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The Florida Keys and Key West vacation packages

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Florida Keys & Key West ... Laid-Back and Legendary

The Florida Keys — the continental United States’ southernmost island chain — are characterized by a balmy subtropical climate, breathtaking natural beauty and a uniquely laid-back atmosphere that seems to be a world away from big cities and every-day cares.

The islands are connected by the Florida Keys Overseas Highway’s 42 bridges — one almost 7 miles long — over the Atlantic Ocean, Florida Bay and the Gulf of Mexico.

The longest island of the Keys chain, Key Largo shares its name with the famous movie starring Humphrey Bogart and Lauren Bacall — portions of which were filmed there. Bogart's Key Largo connection still is evident today as visitors can take a ride on the African Queen, the actual boat he skippered in the movie of the same name. But Key Largo's star attraction is John Pennekamp Coral Reef State Park, the first underwater preserve in the United States, now incorporated within the National Marine Sanctuary.

Islamorada is the centerpiece of a group of islands sometimes referred to as the "purple isles." Known as the Sport Fishing Capital of the World, Islamorada is heralded for its angling diversity and features the Keys' largest fleet of offshore charter and shallow-water "backcountry" boats.

Marathon is a renowned boating and family destination and is centrally located at the heart of the Florida Keys between Key Largo and Key West.

Big Pine Key and the Lower Keys

For more than 60 years, the region of Big Pine Key and the Lower Keys — from the west end of the Seven Mile Bridge at Sunshine Key to Stock Island — has advocated the responsible use and preservation of the vast natural wonders found there. That focus on the environment has earned the region the title of the Natural Keys.

Key West is the final stop on the Overseas Highway, where the land ends and meets the sea amid 19th-century charm and contemporary attractions. Continental America's southernmost city, situated closer to Cuba than to Miami, is characterized by quaint palm-studded streets, century-old mansions and a uniquely relaxing way of life. At day's end in Key West, crowds gather at Mallory Square to experience the nightly "sunset celebration," a tradition that locals share with visitors.

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DISCOVER THE BEST KEY WEST RESTAURANTS, KEY WEST BEACHES, KEY WEST MUSEUMS, AND PLACES TO SNORKEL

March 27, 2024 | 6 min read.

A funny but true story tells you all you need to know about the independent, larger-than-life spirit of tiny Key West, the 4-square-mile island at the southernmost tip of the Florida Keys. It was April 23, 1982, when, in search of illegal drugs, the U.S. Border Patrol set up a roadblock on US 1, the main thoroughfare connecting the keys to the mainland, creating a colossal traffic jam and hampering tourism. Key West city officials implored the federal government to remove the blockade but to no avail. So, they staged a mock secession from the Union, declaring Key West the Conch Republic. Within 60 seconds, they surrendered to the government and asked for a billion dollars in foreign aid. The money never materialized, of course, but the roadblock was removed—and the spirit of the story endures.

Today, locals continue to embrace their “sovereign state of mind” and tongue-in-cheek motto “We seceded where others have failed.” Indeed, along with a sense of humor, Key West brims with a singular sense of place, separated not only by the endless blue Gulf and Atlantic waters but also by its uniquely Conch come-as-you-are attitude and laid-back lifestyle.

If you long for a bit of island time but are short on—well, time, here’s a two-day itinerary that squeezes in a weekend’s worth of fun and sun in Key West. (You can sleep when you get home.)

TOOLING AROUND TOWN While Key West is super-walkable, consider renting transportation (an electric cart, a scooter or a bike, for example) to explore the island’s many corners. Another option: Board the Conch Tour Train or hop-on/hop-off Old Town Trolley to explore a greatest hits collection of attractions.

KEY WEST MUSEUMS Love history? You’ll want to check out the Harry S. Truman Little White House , used as a retreat by Truman and five other US presidents during their presidencies, and the Key West Lighthouse & Keeper’s Quarters Museum , where you can explore the life of a keeper and climb 88 steps to the top of the 1848 lighthouse. Also, drop by the Oldest House Museum , a Bahamian-style home dating to 1829, and the 1891 Key West Museum of Art & History at the Custom House , featuring two floors of exhibitions.

You can also dive deep into the 19th-century Golden Age of Sail when a hundred ships passed by Key West daily, many wrecking along the treacherous reef, making the island a wrecking hot spot. Fascinating shipwreck stories are told at the Shipwreck Treasure Museum , also home to a 65-foot-tall lookout tower and artifacts salvaged from the Isaac Allerton, and the Mel Fisher Maritime Museum , showcasing treasure hunter Mel Fisher’s fortune of finds, including gold, silver and jewels from a 17th-century Spanish galleon.

KEY WEST MUSEUMS FOR LITERARY FANS Key West has a storied reputation as a haven for the literati, with famous writers—including Mark Twain, Wallace Stevens, Robert Frost, Ralph Ellison, Elizabeth Bishop and Shel Silverstein–leaving their mark here. But the most legendary resident was Ernest Hemingway. His former home, a grand Spanish Colonial villa, is now the Ernest Hemingway Home & Museum . Here, you see the writing studio where he penned many a masterpiece and visit with some 60 six-toed cats, which are descendants of Hemingway’s pet feline. Nearby, the Tennessee Williams Museum presents a trove of artifacts related to the celebrated playwright.

KEY WEST GARDENS If nature is your thing, head to The Key West Butterfly & Nature Conservancy , where a glass-domed tropical habitat teems with hundreds of fluttering butterflies, exotic birds and two flamingos. More glorious gardens await at the Audubon House & Tropical Gardens , Key West Tropical Forest & Botanical Garden , and West Martello Towers, a Civil War-era fort turned tropical oasis.

KEY WEST RESTAURANTS AND PLACES TO PARTY Hungry yet? Key West’s multicultural influences translate to a kaleidoscope of island flavors, from Caribbean plates to Cuban specialties to American mainstays. For a quick bite, swing by the Bahama Village for curry- and jerk-infused Caribbean cuisine, the Cuban Coffee Queen for café con leche and Cuban sandwiches or, natch, Margaritaville for the quintessential Cheeseburger in Paradise.

Come evening, Mallory Square is the place to be beginning two hours before sunset. Here, on the promenade overlooking the Gulf of Mexico, a Sunset Celebration unfolds nightly, with magicians, acrobats and stunt performers entertaining the crowds as a prelude to the spectacular sunset.

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KEY WEST SHOPS, ART GALLERIES, RESTAURANTS, AND BARS Then, mosey over to Duvall Street, chockablock with shops, art galleries, restaurants and bars, many presenting live music nightly. Stop by Sloppy Joe’s , once a Hemingway hangout, for an original Sloppy Joe’s sandwich. Then, hop over to Captain Tony’s Saloon , where the late Jimmy Buffett performed and the dive-bar décor includes license plates, bras, business cards and dollar bills plastered everywhere.

GETTING OUT ON THE WATER You cannot visit Key West without getting out on that beautiful turquoise-blue water, of course. A slew of tour operators, many clustered along the Key West Historic Seaport , can take you out on everything from fishing charters to eco-adventures to sunset sails. The crystal-clear, calm waters are perfect for snorkeling, kayaking, paddle-boarding, jet-skiing, scuba-diving and more.

KEY WEST PARKS AND BEACHES You can rent gear from tour operators on several public beaches, or simply enjoy a dip in the water at places like Fort Zachary Taylor Historic State Park , Smathers Beach and Higgs Beach .

For a splurge, take a day trip by high-speed ferry or seaplane to Dry Tortugas National Park , about 70 miles west of the island. Here, you can explore 19th-century Fort Jefferson as well as swim, snorkel and scuba to see an amazing array of marine life inhabiting the coral reef.

MORE TASTE-TEMPTING KEY WEST RESTAURANTS Back at the dock, watch the boats unload their fresh catches of the day. Later, return here for dock-to-dish dining at the many restaurants dotting the seaport. You can’t go wrong with a waterside table at the open-air Conch Republic Seafood Company . For more upscale waterfront dining, make reservations for a balcony table at the A&B Lobster House . And save room for Key West’s iconic dessert: key lime pie. Kermit’s Key Lime Shop whips up some of the island’s best, including Key Lime Pie on a Stick.

Before wrapping up your whirlwind tour, snap a photo at the Southernmost Point , a concrete buoy marking, yep, the southernmost point in the continental US, a mere 90 miles from Cuba. And while you wave good-bye, remember to bring home the ultimate souvenir: some of that colorful Conch spirit.

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South Florida Tourbook Guide

Including florida keys, fort lauderdale, key west and miami-miami beach.

Explore the diverse cultures of South Florida with the digital AAA TourBook guide. The Sunshine State offers everything from beautiful beaches and stunning ocean views to the lush wetlands of the Everglades and the laid back atmosphere of Key West. You'll find opportunities to explore the art and cultures that make up the region. Plan your next trip with the help of AAA's digital TourBook travel guide, available on mobile, tablet or desktop.

With the South Florida guide, you'll get advice from AAA travel experts about the best things to see and do, where to stay and how to plan the trip of a lifetime. You'll learn insider travel tips and answers to many top questions asked by travelers.

Here's a sampling of things you'll find in the South Florida guide.

• What beaches to visit
• Why visit more than the beaches
• What to do in Everglades National Park
• Where to camp, hike and fish in state parks and national public lands
• How to explore the Florida Keys
• Where to find the best diving spots
• What to see in Miami's Art Deco District
• Where to see live coral reef

What are some of the must-dos covered in this guide?

We know no two travelers are alike, so we've included a wide variety of things to do in each TourBook guide, from national parks and recreational activities to museums and theme parks.

We cover top outdoor spots to visit in Miami, including Everglades National Park, South Beach and Fort Lauderdale Beach. Learn about history at the Ernest Hemingway House and Museum in Key West and at the Edison & Ford Winter Estates in Fort Myers, and enjoy viewing the art collections at Frederic and Evelyn Bartlett's gorgeous waterfront estate the Bonnet House Museum & Gardens and at more traditional museums such as Pérez Art Museum Miami. Take the family to the Museum of Discovery and Science to learn about the Everglades ecosystems and local ocean life such as sea turtles.

You'll find all these attractions and more in this digital destination guide.

Will this guide help me plan a road trip?

Yes! This guide includes inspiration for scenic drives in South Florida. You can also use the high-quality maps to get started planning your own route.

Is national park information included?

Yes. The South Florida TourBook includes detailed information and travel tips for Biscayne National Park, Dry Tortugas National Park and Everglades National Park.

You'll also find travel information about Big Cypress National Preserve which contains swamp, marshland, prairie and mangroves and is home to many native species of animals.

Explore the South Florida TourBook guide, and start planning your next travel adventure today!

A Key West getaway + KIDS STAY FREE! with Pleasant Holidays   Varies pp

• Duration: 6 Days
• Destinations: United States

The Reach Key West — Curio Collection by Hilton is set on a private natural-sand beach in Key West. This boutique resort is an intimate and elegant destination with a beautiful shoreline and breathtaking sunshine. Stunning murals and artwork reflect the local culture, and guest rooms feature subtle nods to the resort's nautical roots. Guests can enjoy spectacular views from the privacy of their balcony. This luxury getaway is steps away from world-famous Duval Street and offers spectacular on-site amenities such as an oceanfront pool, deep sea fishing, snorkeling, diving and more. Indulge in a Florida oasis to remember with Pleasant Holidays. 

Founded over 60 years ago, Pleasant Holidays is one of the largest travel companies in the United States offering customized vacation packages all over the world! Plan everything with a AAA Travel advisor - your flight, accommodation preference — all-inclusive or luxury, renting a car, sightseeing activities, and even travel protection coverage to preserve what you have to look forward to.

Special Offers and Member Benefits:

• Kids 17 & younger stay FREE
• Up to $50 per booking savings
• Bounce Back Offer - Up to $100 savings on your next trip**
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Where You Will Stay: 

The Reach Key West, Curio Collection by Hilton is situated oceanside on the only natural sand beach in Key West, boasting stunning views of the exceptional location. The guest rooms feature subtle nods to the hotel's nautical roots. Savor delectable cuisine amid sea breezes on the open-air wood deck of the Four Marlins Restaurant. Bask in the sun at the beachfront pool, or enjoy an array of outdoor activities, including bocce ball and water sports. Besides its prime oceanfront location, the hotel is a brief stroll from major attractions of Old Town Key West. 

What You May See: 

Off-beat, pastel-colored and wonderfully tolerant, Key West retains its sense of humor and humility despite all odds. Perhaps its slogan, One Human Family , says it all. There’s a feeling of community here. The area has attracted some of the most creative souls on the planet for years. Life is usually quite lively in the continental United State's southernmost point. 

Nearby Attractions:

• Old Town Trolley Tours
• Waterfront Playhouse
• Key West Lighthouse 
• Key West Aquarium
• Key West Shipwreck Treasure Museum
• Ghosts & Gravestones
• Conch Tour Train
• Fort Zachary Taylor State Park
• Harry S Truman Little White House

Need help selecting a package?  

With endless choices and options that can be customized, select get a quote below and let us build a vacation that’s perfect for your needs and budget. We’ll book the best package for you directly, and combine it with any AAA promotions to get you the best deal! 

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• And much more!

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All pricing and offers for accommodations and other non-air travel are per person, based on double occupancy, capacity controlled and subject to availability and change without notice. Pricing does not include taxes, fees, fuel surcharges, gratuities, resort fees, or airfare unless otherwise noted and is valid on new bookings only. Prices, fees, and other restrictions are subject to supplier policies. All offers, including but not limited to, bonus amenities, upgrades, prices, and group benefits are based on select dates, resorts, room categories, and/or fare codes. Specialty pricing may require proper identification. Cancellation penalties, blackout dates, and other restrictions may apply. When traveling outside the United States a valid passport is required. It is the sole responsibility of the passenger to have the proper documentation and identification required by the United States and other governments at the time of travel. When passports are required, it must be valid for a minimum of six months past your date of return. AAA strongly recommends the purchase of AAA Travel Protection. Usage of a credit card for travel arrangements may provide additional protection, please consult your credit card policies. Under certain circumstances the package price may be subject to supplemental price increases imposed by the supplier. Price increases include, but are not limited to fuel surcharges, taxes or fluctuations in foreign exchange markets that may be imposed after the date of purchase. Air-inclusive prices do not include government imposed taxes and fees, including but not limited to a September 11th Security Fee, U.S. or international government imposed taxes and fees, Federal Excise Fees, among others. Some carriers charge additional fees for checked bags, fuel surcharge, meals, etc. Please check the carriers website for details. Air-inclusive pricing is based on select departure cities. Prices from other cities may vary. AAA Northeast acts solely as a sales agent for travel suppliers and is not responsible for the actions or inactions of such suppliers. We monitor all of the information presented on our website; however, we do not assume responsibility for any errors or omissions in the content of the offers displayed. Review full Travel Disclosure and Consent at time of booking.

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Best Time to Visit

Weather & Climate

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Things to Do in Key West

Things to Do in the Florida Keys

Best Beaches in Key West

Fishing in Key West

Best Key Lime Pie

Food to Try in the Florida Keys

Top Key West Restaurants

Your Trip to Key West: The Complete Guide

The nation’s southernmost city is filled with fun bars, restaurants, historic homes and museums, beaches, water sports and eclectic characters with stories to tell. A three-hour trip from Miami (you can also fly into Key West International Airport ), the drive to Cayo Hueso is anything but stressful when you’re surrounded by crystal blue, sparkling waters on both sides of the highway. A therapeutic drive forces you to slow down and will get you in the mood for what’s to come—boozing, cruising, and possibly some dolphin-watching. Use this guide to plan your trip including where to stay, what to do, when to go, and more

Planning Your Trip

• Best Time to Visit : Visit between March and May when the weather is milder for South Florida (think 70s and low 80s Fahrenheit and less humidity all around) and there aren't as many tourists.
• Language: English, though there are many native Spanish speakers.
• Currency: U.S. dollar.
• Getting Around: You can rent a car in Key West or use a rideshare app, but a pretty common and somewhat adventurous way to get around Key West is on a Vespa. Many hotels on the island have rental programs for guests, as do local tour companies.
• Travel Tip: If you’re not much of a scooter fan or even a bike rider, you can get around Key West perfectly fine on foot. Old Town is worth exploring at a leisurely pace, anyway. There’s a European-style (above ground) cemetery worth checking out and most of the restaurants, bars, and sights we’ve listed are easily accessible when you’re walking.   

Things to Do

Local bars stay open really late here, and most of them hire local talent to play originals, as well as covers of songs we all love. The Ernest Hemingway Home is a must-do, as is a photo at the southernmost point of the continental U.S.   , designated by an anchored concrete buoy. The well-known tourist attraction has been at the corner of South and Whitehead Streets since 1983 and is one of the most visited and photographed attraction in the Keys.

• You’ll likely end up on Duval Street at some point, where you'll find shopping, dining, and drinking galore.
• Mallory Square is where a daily Sunset Celebration takes place with live entertainment that includes fire breathers and artists of all sorts.
• If tours are more your speed, reserve a spot on the Ghosts and Gravestones trolley tour . Guides combine Key West history with some clever ways to make you scream, so this activity may not be suitable for children under the age of 13. 

Explore more attractions with our full-length article on the best things to do in the Florida Keys.

What to Eat and Drink

If you like seafood, you’re in the right place. It’s always fresh and always perfectly cooked. If you’d rather go fishing and present your catch at a restaurant, they’ll season and cook it for you. While you're in town you have to try a slice of Key lime pie. Some of our favorite restaurants in Key West include El Siboney (Cuban food), Eaton Street Seafood Market & Restaurant (go for the stone crabs), Half Shell Raw Bar (oysters, pelicans and the decor here will leave you wanting more) and Croissants de France (for a full-on carby French breakfast of crepes, fresh-baked pastries and French toast—with a side of eggs for balance).

When it comes to imbibing, the options are endless, but for craft cocktails, Caroline’s Other Side is a cozy, cool bar hidden in a Key West-style home. Breweries are abundant here, too. Waterfront Brewery and First Flight Island Restaurant & Brewery are a couple; there are also rum distilleries (Key West First Legal Rum Distillery) and the down and dirty, good old bars that haven’t changed since they opened, like Sloppy Joe’s (one of Hemingway's favorite haunts   ), Green Parrot Bar, Capt Tony’s Saloon and El Meson de Pepe where you can dance nightly to salsa.

Explore our articles on the best restaurants in Key West , the best places to eat key lime pie in the Florida Keys and the most fun bars .

Where to Stay

Where do we begin? If you want to relax right outside town, there are some newly renovated and reopened hotels worth getting to know, like Havana Cabana, 24 North Hotel, the Perry Hotel Key West and the Gates Hotel. Smack in the middle of the downtown area, though, the possibilities are endless. La Concha Hotel & Spa serves up glamorous 1920s vibes (it opened nearly 100 years ago), Casa Marina Key West, a Waldorf Astoria Resort channels Old Hollywood but in Florida, and the Saint Hotel Key West, an Autograph Collection Hotel, feels dark and mysterious in all the right ways that New Orleans might feel dark and mysterious. Old school bed and breakfasts are abundant in the Southernmost City, too, and there’s something refreshing about booking the old-fashioned way and having bread baskets delivered to your door in the morning.

Explore the best camping spots in the Florida Keys , best hotels for tourists and everything you need to know about visiting the Keys in summer . 

Getting There

You can drive into town (there’s only one road on and off the island  ) or fly into Key West International Airport . While cars are helpful to get around, especially when traveling from one side of the island to the other, most areas are easily walkable. On the rare occasion you’re sailing around the world, or even just the state of Florida, you can dock nearly anywhere on the island. Some hotels give guests the option of parking their boat instead of a car.  

Money Saving Tips

Take advantage of parks and museums that are free of charge for all visitors. Walking, of course, is free, good for you, and a more affordable option than hopping in a rideshare car. If you and everyone in your crew is of legal drinking age, First Legal Rum Distillery offers free rum tastings, with the purchase of one shot glass per person. 

• The Children’s Animal Park has a petting zoo, which will delight kiddos of all ages. 
• The Florida Keys Eco-Discovery Center is another fun and educational place to learn about local plant and animal species. 
• Higgs Beach is free to visit, too. Pack a blanket, a picnic, and lots of water, and spend the day soaking in the sun and saltwater. 

City of Key West, Florida . "Southernmost Point."

VISIT FLORIDA . "Key West."

Key West Chamber of Commerce . "Getting Here."

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The Overseas Highway: Miami to Key West

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The Best Family Road Trips for Every Age

Your Trip to Miami: the Complete Guide

Your Trip to the Bahamas: The Complete Guide

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The 8 Best Beaches in Key West

The Ultimate 3 Day Key West Itinerary (With a Map of Key West)

Are you planning your ultimate Key West vacation but not sure where to start? Keep reading!

In this 3 Day Key West itinerary , I cover all the details you need to know to plan your dream vacation to Key West . I’ll go over the best areas to stay and different hotel options, the top restaurants to check out, and all the fun activities you need to do!

Plus, I’ve organized it all into 3 perfect days so you don’t need to do any more planning or research!

In my opinion, 3 days is the perfect amount of time to spend in Key West for first-timers. 3 days gives you the opportunity to soak in the atmosphere, explore the main sites, and go on 1-2 excursions if you wish!

So whether you’re a history buff, a nature enthusiast, or simply seeking the perfect beachside retreat, this Key West itinerary is designed to make the most of your time in the Conch Republic!

Note: This post contains affiliate links. If you click an affiliate link or book through an affiliate program, I receive a small commission at no cost to you! 

The Ultimate Key West Itinerary: 3 Days in the Conch Republic

Where to stay in key west.

Before we dive into this Key West itinerary, let’s talk about where to stay in the famous Key West!

Key West is only 4 miles long, so you might be thinking… how many places can there possibly be to stay? The answer is… a lot!

Key West has a few diverse neighborhoods, but the first decision you’ll need to make is whether you prefer the historic charm of Old Town or the modern amenities of New Town. These two areas split Key West down the middle: the eastern half and the western half.

Most people want to stay in Old Town to be near the action, but there are pros and cons to both areas, which I’ll dive into in the next sections!

Staying in Old Town Key West

For those seeking a slice of Key West’s rich history and vibrant atmosphere, Old Town is the ideal choice. This area is known for its charming streets lined with Victorian-style houses, art galleries, and boutique shops.

When staying in Old Town, you’ll be steps away from the iconic sites. You can explore the Hemingway Home and Museum, soak in the vibrant energy of Mallory Square, and party the night away on Duval Street, then walk back to your accommodation!

Here is a list of the top Old Town Key West hotels , but you can also check out your options on the map above! Old Town has tons of vacation rental and B&B options as well as typical hotels!

• Almond Tree Inn (Moderate)
• Ocean Key Resort (Moderate/Luxury)
• The Mansion on the Sea (Moderate/Luxury)
• Pier House Resort & Spa (Moderate/Luxury)
• Marquesa Hotel (Luxury)
• Casa Marina Key West (Luxury)

If you’re staying in Old Town, I recommend skipping the rental car . You’ll be able to access everything you need via walking or biking. Parking in Old Town can be difficult and expensive, so it’s better not to have a car!

However, if you plan to visit other Keys during your stay, you’ll definitely need a car! I recommend doing an epic road trip from Key Largo to Key Wes t so you can experience all the Keys have to offer!

Staying in New Town Key West

If you’re driving into the Keys, New Town is the first area you’ll come across. It’s where the airport is located, along with most of the “chain” hotels. This area is characterized by wider streets, modern conveniences, and a quieter ambiance compared to the lively energy of Old Town.

New Town provides a more relaxed environment, making it an excellent choice for those looking to unwind after a day of exploration. It’s also convenient for those who prefer to have modern amenities at their fingertips.

Hotels in New Town also tend to be a bit cheaper than those in Old Town!

Even though it’s a bit further away from the main Key West attractions, you still may not need a car if you’re staying in New Town.

This is because most of the hotels in New Town have free shuttles to Old Town that run multiple times a day. These shuttles make it easy to visit Old Town without having to worry about parking, or drinking and driving!

Here is a list of the top hotels to check out in New Town Key West!

• Havana Cabana at Key West (Budget/Moderate)
• Parrot Key Hotel & Villas (Moderate)
• Margaritaville Beach House (Moderate)
• The Perry Hotel and Marina (Moderate)
• Hilton Garden Inn (Moderate)

How to Get to Key West

If you’re planning a Key West vacation, you’re going to need to know how to get there! There are a couple of options when it comes to traveling to Key West.

The Key West International Airport (EWY) is extremely convenient to fly into. It’s located right in the heart of New Town and just minutes away from Old Town. If you have the option, I highly recommend flying into Key West.

However, you may find that flights into EWY can be a little pricey. While there are direct flights from around the country, it is still a small airport, which tends to mean higher prices. Airlines like Silver and Allegiant often have cheap, direct flights though, so check to see if they fly out of your home airport!

The other option is to of course: drive! If flight prices into Key West Airport are too high, you can look into Miami Airport (MIA) or Fort Lauderdale Airport (FLL) and then make the drive down to Key West.

I touch more on this in my Ultimate Florida Keys Travel Guide , but I highly recommend this route so you can experience ALL of the Keys, not just Key West. The best option is to fly into Miami, rent a car, and make the drive from Miami to Key West .

Once you arrive in Key West, you can drop off your rental car and fly out of the Key West airport, so you don’t have to drive the length of the Keys twice!

Key West Map

Lastly, before we get into this Key West itinerary, here is a detailed map of Key West! It includes all of the restaurants, bars, and landmarks mentioned in this itinerary, plus more!

Make sure to save this map of Key West to your own Google Maps so you can access it during your trip!

Day 1: Brunch, Historic Sites & a Sunset Celebration

Blue heaven + exploring old town.

Today is your first full day in Key West! Welcome to paradise!

Start your morning by heading straight to Blue Heaven , one of the most popular restaurants. They open at 8am , and I recommend getting there as close to opening as possible. If you show up later in the morning, be prepared to wait!

I highly recommend getting the Lobster Eggs Benedict and a slice of their GIANT Key Lime Pie!

After breakfast, it’s time to walk around Old Town Key West and explore the historic sites. There are a ton of things to do in the area, so you can choose a few (or all!) of them to fill your morning. Here are a few options!

• Climb to the top of the Key West Lighthouse
• Snap a picture at the Southernmost Point
• Tour Ernest Hemingway’s Home & Museum
• Explore the Key West Butterfly and Nature Conservatory

There are also some great lunch spots around this area, including The Lobster Shack , the Seaside Cafe at the Mansion , and Louie’s Backyard !

Beach Relaxation & Sunset Views

In the afternoon, head over to Fort Zachary Taylor State Park , a 19th-century fort and park located on the southern edge of Key West. Starting at $4.50 per person, the park is a great place to spend an afternoon.

There is a beautiful beach within the park where you can swim, lounge, and even snorkel ! Plus, you can explore the fort’s grounds and learn about the incredible Civil War history.

To finish off your day, make your way to Mallory Square and witness the famous Sunset Celebration . This is the most famous place to watch the sunset in Key West, so if you want a front-row seat, arrive early!

Around sunset, Mallory Square comes alive with food vendors, street performers, music, and more. It’s the perfect way to finish off your first night in Key West.

Day 2: Ocean Adventures & Duval Street

A morning ocean adventure.

On Day 2 of this Key West itinerary, it’s time to get out on the water. You have a couple of options!

If you’re feeling adventurous, I highly recommend visiting Fort Jefferson at Dry Tortugas National Park. a former military installation approximately 60 miles west of Key West in the middle of the ocean.

To get here, you either need to take the 3-hour Yankee Freedom ferry or book a seaplane . (The latter is very pricey!!). Both options book up pretty far in advance, so I recommend looking at your options as soon as possible! You can read more about visiting here .

Fort Jefferson is one of the coolest places I’ve ever visited! The fort was never finished, but it was used during the Civil War and even held prisoners.

You can spend the day walking around the fort and enjoying the scenery. Plus there are incredible beaches and clear water surrounding the fort that you can snorkel and swim in. You can even camp here if you’re into that!!

If Fort Jefferson doesn’t sound like your cup of tea, there are plenty of other ocean adventures to be had locally in Key West. Here are some options!

• Snorkeling & Dolphin Watching Combo Tour
• Reef Snorkel & Sail Adventure
• Key West Scuba Dive
• Jet Skiing around Key West
• Island Adventure Eco Tour

No matter which you choose, you are sure to see some incredible marine life and have a great time on the beautiful Key West water! For breakfast before, head to the Cuban Coffee Queen!

A Night on Duval Street

In the evening, head back down to Old Town and grab dinner at one of the fabulous restaurants nearby. If you want to be on the water, I highly recommend Hot Tin Roof at the Ocean Key Resort. This is a great spot if you can’t get enough of those Key West sunset views! You can also grab pre-dinner drinks at Sunset Pier!

There are also some incredible restaurant options along Duval Street, including Blackfin Bistro , Kaya Island Eats , and Nine One Five .

After dinner, it’s time to check out the famous nightlife in the area and maybe do the “Duval Crawl”. This is the nickname for bar-hopping along Duval Street, as you will be crawling by the end!

Some of the most famous bars on Duval include Hog’s Breath Saloon, Sloppy Joe’s, the Bull and Whistle Bar, and the Smokin’ Tuna Saloon.

If dive bars aren’t your thing, don’t worry! There are other nighttime options on Duval Street. You can grab an incredible, adult-friendly dessert at the legendary Better Than Sex restaurant. Another option is to see a drag show at Aqua Nightclub or La Te Da ! Or you can just wander down the street and appreciate the chaos.

Day 3: Bikes, Beach, & a Sunset Cruise

Biking to the beach.

On the last day of this Key West itinerary, start your morning by renting bikes and exploring the south side of Key West. There are plenty of places to rent bikes from, but I highly recommend Eaton Bikes ! They will even drop off the bikes at your hotel for you.

Key West is extremely bike-friendly, so don’t worry about following a particular route, just make your way towards Smathers Beach. There’s a beautiful bike and walking path along A1A in front of the beach you can check out!

Once you’re ready to rest, head onto the gorgeous Smathers Beach, one of the only sprawling white-sand beaches in the entire Florida Keys! This man-made beach actually had white sand imported from the Bahamas, and it does not disappoint! It’s one of my favorite free things to do in Key West !

Shopping and Sunset Cruise

In the afternoon, head back down to Old Town and explore any other sites you missed on your first day. Around Mallory Square, there’s the Key West Aquarium, the Truman Little White House, and the Maritime Museum!

It’s also fun to explore Duval Street during the day! There are many great boutiques and souvenir shops to check out. Make sure to stop in Kermit’s Key Lime Pie Shoppe for another slice of Key lime pie!

In the evening, it’s time to close out your last night in Key West by embarking on a sunset cruise! As you already know, the sunsets in Key West are jaw-dropping, and the best way to see them is from the water on a sunset sail.

There are tons of different Key West sunset cruises to choose from, including dinner cruises, open bar cruises, and cruises with a dance floor! They typically last between 2 and 3 hours and will take you around Key West and Sunset Key as the sun sinks into the ocean.

You can check out my complete guide to Key West Sunset Cruises here to compare prices and help pick the perfect one for you!

Final Thoughts

That wraps up my perfect 3 Day Key West itinerary. As you can see, Key West is more than just an island destination; it’s a kaleidoscope of history, culture, and natural beauty that is sure to leave you wanting more!

And 3 days is the perfect amount of time to spend in Key West to be able to see and do it all. If you follow this 3 day itinerary, I guarantee you’ll have an incredible time!

Don’t forget to check out my other Florida Keys blog posts to help plan your epic adventure! 25 Epic Things to Do in Key West Best Time to Visit the Florida Keys Key Largo vs Key West Should You Visit Key West in January? Yes! Here’s Why

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Your Key West Vacation

From its relaxed vibe to its beaches and beyond, there's a lot to like about Key West. Discover the wonders of this captivating city with a Key West vacation package that's tailor-made for you. A trip to Key West is an excellent opportunity to see the sights. Be sure to visit popular attractions like Ernest Hemingway Home and Museum , Audubon House and Tropical Gardens and Mallory Square . No matter your travel plans or budget, organizing a tailored Key West vacation is simple with Expedia.

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Where to stay in key west.

Key West Historic District

Old Town Key West boasts a rich history with 2485 historic buildings, and is home to popular attractions like Ernest Hemingway House and Mallory Square. Enjoy the lively atmosphere in the central business district.

Old Town Key West

Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area.

Though New Town might not have many top sights, you can venture to the surrounding area to see attractions like Smathers Beach and Key West Tropical Forest and Botanical Garden.

Truman Annex

Mixed-use redevelopment featuring classic conch style homes, high-end condos, a hotel, parks, marina, and museums, including the historic Little White House. Enjoy retail and commercial spaces within the community.

Historic Seaport

Many of the best parts of the southern portion of Florida are rolled into one location. Enjoy your time experiencing attractions in this historic area.

Key West Luxury Vacation Packages

We all deserve to spoil ourselves from time to time, so why not splurge on your vacation in Key West? Book one of our Key West Luxury Vacation Packages and experience stays that come with the best of everything, from poolside bars and first-rate spas to a smorgasbord of restaurants and round-the-clock concierge services. Aside from being perfectly pampering, luxury vacations in Key West should also be stress-free and relaxing.

If it’s peace and seclusion you’re seeking, escape to Casa Marina Key West, Curio Collection by Hilton . A private beach, a signature “toes in the sand” dining experience and yoga sessions are just the start of the offerings at this 5-star resort. Add the Hyatt Centric Key West Resort & Spa to your Key West vacation package and take your escape to another level. An award-winning spa, a private boat dock and a year-round outdoor pool are part of the experience at this upmarket getaway.

Romantic Vacation Packages in Key West

If you’re dreaming of waking up to ocean views, taking long walks along the beach and enjoying candlelit dinners with your honey, check out our Key West Romantic Vacation Packages . A popular destination for honeymooners, Key West is home to idyllic stays that cater to lovebirds, like Pier House Resort & Spa . It has everything newlyweds need: a full-service spa, hot tubs and a private white-sand beach, as well as an excellent location close to lively Mallory Square . Or, stroll hand-in-hand along garden paths and relax under poolside cabanas at Southernmost Beach Resort during your vacation in Key West.

When you can tear yourself away from your cozy surroundings, get out and do the things you love with the one you love. Make new memories with a Key West Photo Shoot at Your Resort or the Beach . Or take the first step toward your new life together and book a Key West Marriage Proposal Package . Browse our Things to Do in Key West guide and add some romantic tours and experiences to your Key West vacation package.

Where to Stay in Key West

Key West is a sun-soaked island-city perched at the western edge of the Florida Keys. Here’s our roundup of the best neighborhoods to stay for your vacation in Key West:

• Key West Historic District : In this busy area you’ll find historical landmarks, superb museums and pretty gardens alongside great shopping, dining and nightlife.
• Duval Street : Packed with retail outlets, bars, restaurants, live music venues and street performers, the fun never ends on this lively street.
• Historic Seaport : Key West’s bustling marina is the place to be for tasty eats, art and water sports excursions.
• Bahama Village : Into architecture and food? Stay in this neighborhood to enjoy its colorful houses and dine at open-air restaurants.
• New Town : If you want to be away from the tourist crowds yet a short hop from major sights, laid-back New Town is the perfect place to spend your vacation in Key West.

Top Things to Do

Whether you want to be active or take things slow, visit a museum or feast until your heart’s content, vacations to Key West offer something for all types of travelers:

• Historical : Get a local history and culture fix at Ernest Hemingway Home and Museum and Harry S. Truman Little White House . Don’t miss Dry Tortugas National Park either.
• Beach : Sun, sea, sand and water sports are the order of the day at popular spots like Smathers Beach , South Beach and Higgs Beach .
• Entertainment : Head to Mallory Square for street performers, food carts and spectacular sunsets. If you’re in the mood to party, join a Key West pub crawl or a craft cocktail crawl .
• Family-Friendly : Traveling with the kids? There’s fun for all ages at the Key West Shipwreck Museum and Key West Aquarium .
• Sports : It’s time to get adventurous! Add a Snorkel Adventure of Coral Reef to your Key West vacation package or try parasailing . Alternatively, join a Key West Mangrove Kayak Eco Tour .

How to Find Cheap Package Deals

Landing the best deals on vacations to Key West is a breeze. Just key in your preferred travel dates and filter your property search by things like amenities, price and star ratings. A top tip for scoring a cheap hotel in Key West is to arrive in June, July and August. Generally, hotels are less expensive and have more availability around this time. December, January and February are the busiest months in Key West.

Key West Essential Information

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Frequently asked questions, discover the most popular places to visit in key west, duval street.

Along one of the southernmost streets in the continental U.S., enjoy a lively area filled with shops, pubs, restaurants and lots of sidewalk acts and vendors.

Dry Tortugas National Park

Separated from the mainland and encased by golden beaches and colorful coral reefs, this is a national park of fascinating ocean scenery.

Smathers Beach

Key West’s popular party beach has an electric atmosphere on the weekends and is a destination for water sports lovers.

What to do in Key West

Morning coral reef snorkel excursion with unlimited mimosas & breakfast, sunset dinner cruise with unlimited open bar, other vacations you might like.

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3 Days in Key West: An Epic Weekend In Key West Itinerary

February 24, 2022 //  by  Florida Trippers

Are you looking for the perfect weekend in Key West? If so we have put together a three-day itinerary for your weekend in Key West! We have put together the best things to do in Key West . Your weekend in the Keys will be spent enjoying history, restaurants, state and National parks, beaches, nightlife, and more. We have crafted a plethora of tours to enjoy on your weekend trip to Key West!

Planning your trip to Key West last minute?

Make sure to book ahead! Hotels and tours often sell out the closer you get to your trip. Here are our top picks for Key West!

Top Experiences And Tours In Key West:

• Dolphin Watching And Snorkeling Eco Tour (Top pick!)
• Schooner Sunset Sail (2 hours)
• Reef Snorkel From Key West (Includes breakfast and mimosas)
• Hop-On Hop-Off Trolley Tour (Great way to see the city)

Top Places To Stay In Key West:

• Margaritaville Beach House Key West (Modern mid-range)
• Blue Marlin Motel (Affordable in downtown)
• Hampton Inn Key West (Waterfront with pool)
• Wicker Guesthouse (Great location!)

The first day of your Key West Itinerary will be spent exploring all the historical sites in Key West, the second day will take you to Dry Tortugas National park or Bahia Honda State Park and Day three will be spent exploring a corral, a food tour and shopping.

Before you plan your trip, make sure to check out The Best Times To Visit The Keys where we break down each month and talk all things weather!

Getting To Key West

Getting to a Key West weekend getaway is very easy! You can arrive by car, plane or boat.

If arriving by plane, the closest large international airport is Miami (MIA). Located just about a 3 hour drive north. If you do not want to rent a car, there is a shuttle bus from both FLL and MIA airport to Key West. However, you can also fly into Key West airport!

If driving you have the opportunity to stop along your drive through the Florida Keys. Located about 160 miles south of Miami, why not explore the upper and middle keys on your way to your weekend getaway in Key West.

For those coming from Fort Myers or Marco Beach areas, you can take the Key West Express ferry. The journey is 3.5 hours.

Getting Around During Your Key West Weekend Trip

We HIGHLY recommend renting electric bikes to explore during your weekend trip to Key West. It is such a fun way to explore with the fresh ocean breeze on your Key West weekend getaway. Another fun way to see the city is on a bike tour complete with a slice of Key Lime pie after biking all day!

You can use your own car if driving or rent a car at the airport. This is a great option if you want to explore the upper and middle Keys on a long weekend in key west.

Uber is easy to find here, and the hotels have shuttles. Key West is also a very walkable city, and you explore the downtown area on foot. Or try the hop on the hop-off trolley that operates through the city. You can book a tour here !

Are you a history buff? On the first day of your Key West weekend itinerary, we suggest exploring the historic sites across downtown Key West. Explore the home of a great American author or the winter getaways of former U.S. Presidents!

After a full day exploring and learning the history, it will be time to let loose on your weekend in Key West! Head on one of the amazing sunset cruises around the harbor or stay on land and enjoy a pub crawl across Duval street!

Stop 1 : Breakfast in Mallory Square

Located on the water in the Old Town, Mallory Square is the center of Key West. The Square has shops and restaurants that the whole family can enjoy! Why not start your day with breakfast here! We suggest breakfast at Cuban Coffee Queen.

Choose a hearty Key West-style breakfast or a Cuban breakfast to start fueling your body before spending the day exploring Key West!

After breakfast explore Mallory Square where street vendors and performers are often present.

Stop 2 : Harry S. Truman’s Little White House

Built in the 1890s, Harry Truman’s Little White House is Florida’s only presidential museum and is one of the best places to learn about American history.

Named after Harry Truman as he used this home as a winter getaway from DC. He use the house from 1946 through 1952. Presidents Taft, Eisenhower, Kennedy, Carter, and Clinton have all visited as well.

The entrance is $20 per adult or $10 per child. Included is a tour of the home and grounds where visitors can see how presidents lived while on their weekend in Key West!

Stop 3: Ernest Hemingway House

The next stop on your Key West itinerary is the Ernest Hemingway House . Located just a block from Duval street, the Hemingway House is a Spanish Colonial-style mansion. It is full of the famous writer’s personal items, historic furnishings, photographs, paintings, and more.

This is a must-see Key West destination for anyone who loves history, architecture, or literature! Worth noting the grounds are filled with the famous six-toe cats that are descendants of cats that roamed the grounds while Hemingway himself lived in the house!

Stop 4 – Sunset Cruise

Whether you are in town for a Key West couples getaway , a Key West girlfriend getaway, or a Key West bachelorette party we have the perfect way to end your first day! Why not end your first day with a Sunset Cruise with Buffet Dinner and Open Bar! There is truly nothing like being out on the calm and peaceful ocean while watching a gorgeous sunset.

On this two-hour cruise around the harbor, you will be fed a delicious dinner with favorites including pulled pork in mojo sauce, black beans, and rice, fish, mixed vegetables, pasta with mini shrimp, and more. You can dance on the upper deck, or sip a cocktail and watch the sunset!

For those looking for something a little more relaxing why not hop aboard the 2-Hour Sunset Sail on Schooner America 2.0 tour with two viewing decks and the calmness of open water.

Optional: Stop 5 -Pub Crawl

If you would rather stay on land, to end your first night on your weekend trip to the Florida Keys try a Duval Street Pub Crawl! Key West is known for its nightlife on Duval street, so why not let a tour guide you into the hottest spots in town with your admission and a cocktail at each stop included!

For those looking for a fun night out why not book this Drag Queen Guided tour that takes you to the most happening nighttime destinations in Key West! Featuring drinks, karaoke sing-alongs, dancing, and all the drama that comes along with being in the presence of a world-famous drag performer!

Make sure to check out the best bars and nightlife in Key West!

On Day 2 of your weekend in key west, we suggest heading on a day trip to Dry Tortugas! You can either do a half-day seaplane tour or a full-day boat tour! Check out our guide to avoid the big mistakes plus tips when visiting Dry Tortugas National Park !

After your trip to one of the best and hardest to reach National Parks, why not relax downtown and grab dinner and drinks on the water! You can pack and lunch even an alcoholic beverage to enjoy while on the island!

If getting to the Dry Tortugas is not an option on your trip, why take a day trip to Bahia Honda State Park!

Stop 1 : Dry Tortugas Day Trip

Dry Tortugas is a 100-square mile park made up of seven small islands and is located just about 80 miles from Key West. This tropical paradise is also home to the well-known and magnificent Fort Jefferson. A visit here mixes nature, history, and transports visitors to a remote place!

The only way to visit here is by private or chartered boat tour , chartered seaplane tour, or the Yankee Freedom Ferry . Reservations for the ferry fill up very quickly, so you’ll need to plan several months in advance. It is worth noting that the visit to Dry Tortugas can cost several hundred dollars and needs to be booked in advance. But it is 100% worth it!

For those who are adventurous enough, why not spend the night for some primitive camping in Florida !

Stop 2 : Visit Fort Jefferson

Most of the iconic photos you see from the Dry Tortugas is the red brick, Fort Jefferson. Take a tour of Fort Jefferson to learn about the island chain’s historical past as a prison. It once housed nearly 2000 inmates. You can also take a self-guided tour as well with numerous plaques spread across the fort. Make sure to put this on your list when doing a Florida Keys Road Trip!

Stop 3: Snorkling

No weekend in Key West is complete without a trip to Dry Tortugas. It is a great spot for snorkeling and scuba diving around the National Park. Less than 1% of the National Park is on dry ground, making the Dry Tortugas an underwater paradise!

With crystal clear water, gorgeous coral some rising 50ft high, it is truly spectacular! There are fish species here that don’t exist anywhere else in the world. Keep an eye out for  sea turtles as the island is named after the Spanish word for turtles!

The popular spots to go, scuba dive, include the Maze, the Bat Caves, Dante’s Inferno, Texas Rock, and the Windjammer Wreck one of the most beautiful shipwrecks in the world.

Optional: Bahia Honda State Park

For those who don’t have the time or budget for Dry Tortugas, head to Bahia Honda State Park . We have an entire guide on what to explore here!

Known for its iconic Florida Key scenery, sandy beaches, clear waters Bahia Honda State Park is the best place to visit on a weekend in Key West. Just under 40 miles from Key West, it only costs $8 per vehicle to visit!

You will want to arrive early on weekends or holidays as once capacity is hit, the park will close!

Make sure to check out some of our other favorite things to do in the Lower Keys in addition to Bahia Honda or check out our list of the Best Florida Keys Beaches for some more ideas of places to visit!

Stop 4: Dinner at Blue Heaven

You are sure to have worked up an appetite after exploring Dry Tortugas! We suggest heading to one of the best restaurants in Key West for dinner.

Head to the historic Bahama Village where you can enjoy the island flavors. From the fresh snapper in the yellow submarine sandwich to popular Caribbean “BBQ” shrimp or a vegan and vegetarian option, there are plenty of options!

Stop 5: Ghost Tour

After you return from your half-day trip to Dry Tortugas or Bahia Honda, why not spend your evening on a ghost tour of Key West! The best part is you will be transported by trolly along with the spooky and haunted sites across the island.

On day 3 of your weekend in Key West itinerary, you will be taking it easy after a jam-packed first two days and nights! You will start with an amazing boozy brunch spot, followed by either snorkeling the reef, taking food out, or purchasing handmade leather sandals!

Stop 1: Brunch at Bagatella

Bagatelle serves a breakfast hangover happy hour from 9 to 11:30 a.m. every morning. If you had a late night during your Key West bachelorette party head here, where you can enjoy fun alcoholic beverages with scrumptious brunch plates. Dive into a crab cake benedict, crispy fried French toast, or braised pork sandwich with pineapple slaw.

Stop 2 : Snorkeling and Breakfast

On stop 2 of your Key West getaway itinerary why not take a Key West: Reef Snorkel Morning Tour with Breakfast & Mimosas! This tour is 3 hours where you will visit the third longest reef in the world, snorkel, and enjoy a delicious breakfast accompanied by mimosas on your trip back to port!

Stop 3: Optional : Key West Food Tour

Next up, for those who want to stay on land is a Southernmost Food and Cultural Wal k ing Tour ! On this 5 stop tour, you will get to taste some of the most famous foods of Key West. Think conch fritters, fresh fish tacos, and the amazing key lime pie! Head to hole-in-the-wall places you would never find on your own!

Stop 4: Smather’s Beach

On your 3 days in Key West, you must visit one of the beaches. With half a mile of soft sand, Smathers Beach is the one to go to if you like lively, fun-filled beaches.

Smathers is a great beach with something for everyone like swimming, snorkeling, kayaking, parasailing, sunbathing, and beach volleyball. Plus there are food vendors and beautiful palm trees shoreline perfect for picnicking under!

Stop 5: Kino Sandal Factory

Since 1966, the Kino Factory has been a staple of any Key West weekend trip! Stop in the purchase handmade leather sandals that are hand-cut and produced on-site in this traditional sandal factory! Choose from over 17 styles with various color combinations for men, women, and children. 

Where To Stay In Key West

There are plenty of options if looking for places to stay in Key West ! From hotels, home rentals , camping , and more!

Make sure to check out our list of the Best Resorts In The Florida Keys ! There are some really epic resorts featured for couples, families, and more.

The Saint Hotel Key West, Autograph Collection

If you are looking to be in the heart of the action, The Saint is located just 4 minutes from Duval Street. This upscale hotel is also close to Ernest Hemingway and Smathers Beach. While the rooms are small, they are well-appointed and bright and airy, or splurge for a much larger suite!

Amenities include a restaurant and bar on-site as well as a chic outdoor pool with a waterfall and Dj on the weekends.

Check Rates: Booking.com

Key West Marriott Beachside

On our most recent trip to Key West, we stayed at the Key West Marriott Beachside. Located on 7 prime acres with oceanfront access with the pool as the centerpiece of the resort. This is truly one of the Best Places To Stay in The Florida Keys!

From the hotel’s marina, you can rent jet skis, kayaks, and paddleboards. There is a complimentary hotel shuttle downtown multiple times daily. Many of the balconies are oceanfront allowing you to relax and enjoy a sunset or ocean breeze from your town room!

If you have a car parking is $25 a night!

Dog-Friendly Home With Private Pool

Are you planning an extended weekend in Key West and want to bring your pups with you? This  Dog-Friendly Home With Private Pool  is the place to stay!

Located in Central Key West, you are in a prime location for exploring shops, restaurants, beaches, historic landmarks, and dog parks! The home is ready to accommodate up to 3 guests with 2 bedrooms, 2 beds, and 1 bath.

>>>Check Rates:  VRBO.com

Waterfront Oasis 

This 2 bedroom 2 bath home has amazing views of the ocean. This property  can sleep 6 people in 4 beds. This is truly one of the Best Places To Stay In Key West!

The property features plenty of outdoor seating, a grill, and a pool table. The home comes with life jackets and kayaks so that you can explore the channel that the house sits on.

Where to Eat During Your 3 days in Key West

Latitudes is one of the classiest restaurants in Key West. To reach it you’ll have to hop on a free ferry because Latitudes is on an island of its own!

With waterfront seating, delicious food, and excellent service, it’s open for breakfast, lunch, and dinner. For breakfast, savor the lobster benedict. For lunch, try the surf & turf burger. And for dinner, twirl up the Key West pink shrimp carbonara or cut into the lemon glazed yellowtail snapper.

Banana Café

This French-inspired restaurant serves up some of the best crepes in town. Enjoy them for breakfast, lunch, or dinner.

Try everything from the breakfast-themed la super crepe to the seafood-filled la Mahi piccata crepe to the popular homemade key lime pie crepe. At lunch, be a little adventurous and try the baked escargot. Or for dinner enjoy the half roasted duck, seafood risotto, and French country chicken. There are also a good number of vegetarian options available at Banana Café.

Hogfish Bar & Grill

Situated on Stock Island just 15 minutes from Key West, is Hogfish Bar and Grill. Known for its fresh seafood and oceanfront location, it is frequented by Florida Keys locals.

The hogfish tacos and hogfish sandwich – named after both the fish and the restaurant – are two of the most popular items on the menu. There is live music on the weekends.

Those looking for vegan and vegetarian options will want to head to The Cafe. Breakfast is served every Monday through Friday until noon. If a dish on the menu doesn’t fit your dietary habits, then simply ask your server for the vegetarian or vegan version.

On Saturday and Sunday, mornings switch to brunch service! We love the Polenta Cake Benedict with lemon-caper hollandaise. You can’t go wrong with the Caprese Egg Sandwich with house basil pesto, garlic spinach, grilled tomatoes, and fresh mozzarella.

Key West vacations

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Here are a few of our most popular Key West resorts:

Combining distinctive island flavor with a fun atmosphere.

Conveniently located where the Gulf of Mexico meets the Atlantic Ocean.

Key West via Fort Lauderdale

Encounter picturesque views and upscale Floridian touches.

Things to do in Key West, FL

Old Town Trolley

The Ernest Hemingway Home and Museum Tour

Key West Glass-Bottom Boat Tour

Key West Living Coral Reef Snorkel Adventure

Here are a few favorites:.

• Enjoy life at sea with snorkeling, sailing, kayaking and paddle boarding tours
• Check out local watering holes on a pub crawl
• See the island at night on a sunset cruise
• Take out a fishing charter to catch exotic marine life

No matter what you’re interests are, you can always find a spot at a world-renowned Key West beach. Experience the full Key West vacation package by booking with Southwest Vacations® today.

Additional information on Key West activities:

Key West exudes character with its quirky charm, natural island beauty, and rich history. Located at the southernmost tip of Florida, a Key West vacation is a true getaway and feels like a Caribbean vacation. It’s a popular destination for a variety of travelers–from families and fishermen to beachgoers and partiers, Key West is sure to keep everyone entertained.

A Key West vacation package offers many activities to choose from including boating, cruises, ecotourism, excursions, scuba diving, snorkeling, and more. The Dry Tortugas National Park is a draw for visitors looking to experience the wilderness of Key West. History and culture buffs will enjoy Fort Jefferson, one of the oldest coastal forts in the United States. Other must-see Key West attractions include the Ernest Hemingway Home and Museum, the Key West Aquarium, and the fascinating Dolphin Research Center.

Scuba diving and snorkeling in Key West is one of the area’s most popular activities. Known as an excellent dive destination, make sure your Key West vacation package includes a tour of the beautiful underwater world of Key West. You can explore colorful coral reefs that are home to many species of tropical fish, explore sunken shipwrecks, or try an exciting night dive where you can experience Key West nightlife underwater.

You can also explore the breathtaking natural beauty and exotic wildlife. With an ecotourism Key West vacation, you uncover scenic treasures hidden under the waves through glass bottom boat tours of the reef system. Popular Key West eco-excursions include cruises along the island where guests can encounter dolphins, manatees, and many other species of wildlife. Eco-tours make for a great addition to any Key West vacation package from Southwest Vacations.

Please note: flight service for Key West vacations is into Ft. Lauderdale.

Key West Vacation FAQ

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Key West flight + hotel vacation packages

Pier House Resort & Spa

Ibis Bay Beach Resort

Casa Marina Key West, Curio Collection by Hilton

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Southernmost Beach Resort

Top key west hotels deals.

Oceans Edge Key West Resort, Hotel & Marina

Margaritaville Beach House Key West

Fairfield Inn and Suites by Marriott Key West

Havana Cabana at Key West

24 North Hotel Key West

Popular places to visit, duval street.

With a visit to Duval Street, a favorite shopping spot in Key West, you can search for that perfect souvenir. Wander the seaside or discover the area's beautiful sunsets.

Dry Tortugas National Park

Separated from the mainland and encased by golden beaches and colorful coral reefs, this is a national park of fascinating ocean scenery.

Smathers Beach

Key West’s popular party beach has an electric atmosphere on the weekends and is a destination for water sports lovers.

Photos of local treasures

Browse Key West vacation photos for more inspiration

Frequently asked questions

Where to stay in key west: best areas for travelers.

• Old Town : Things don't get quiet after dark in these parts. Live it up at places like Key West Burlesque Theater. Pulled an all-nighter? Don't worry about it. You can have a long sleep-in not far away at the Luxury Townhouse in the Gallery District of Old Town, Key West , The Chelsea House or the Almond Tree Inn .
• Key West Historic District : Ernest Hemingway Home and Museum is just one of the awesome sights that draw visitors to this neighborhood. You'll find a range of comfy hotels to take your pick of here, like the Curry # 6 Historical Lodging in the Heart of Old Town! Pool and Breakfast! , The Merlin Guest House and The Marquesa Hotel . Secure your room in advance and be close to the action!
• Truman Annex : Stay a few nights at the Spacious Truman Annex End Unit Townhouse /side Courtyard , the Craig & Cindy Truman Annex Foundry Townhouses or the Hyatt Sunset Harbor Lobster Mini Season and get ready to check some of this neighborhood's prominent attractions off your must-do list. Harry S. Truman Little White House, Mel Fisher Maritime Museum and Key West Museum of Art and History are among the hot spots here.
• Historic Seaport : This place has everything you need — a buzzing vibe, a good variety of hotels and huge attractions, such as Audubon House and Tropical Gardens. Explore what this neighborhood has to offer before unwinding in comfort at the Vacation Paradise, Design Unit FOR 4 Guests, 3 Pools, Bar, Close TO Attractions , the Vacation Paradise, Design Unit FOR 4 Guests, 3 Pools, Bar, Close TO Attractions or the KEY West Escape! Three Amazing Units FOR 12 Guests! Pool, Tiki-bar, GYM .
• Uptown - Upper Duval : If this is your first visit to this city, this neighborhood is a top choice. As well as having a nice selection of hotels to pick from, there are also lots of things to do. Spend your days perusing some of the area's best sights like Key West Butterfly and Nature Conservatory and your nights somewhere comfortable, like The Southernmost Inn-Adults Only , the H2O Suites - Adults Only or the Best Western Hibiscus Motel .
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• There are loads of types of vacations in Key West and the cost will depend on what type of trip you’re taking and for how long you’d like to stay. Here are the latest prices for a 3 night trip for 2 travelers: Top vacation $614; Family vacation $582; Romantic vacation $578; Luxury vacation $708.

Why should you book a vacation package to Key West?

There are many points of interest along Key West, including Ernest Hemingway's home, Dry Tortugas National Park, Martello Towers, and the Key West Aquarium. A rental car is the easiest way to travel at your leisure between these popular cultural attractions.

When should you book a vacation package to Key West?

The best time to visit is between March and May before the heat and crowds of summer tourists arrive. However some of the most popular cultural festivals include Ernest Hemingway Days, Goombay Festival, and Fantasy Fest, which take place in the summer and fall.

Where should you stay in Key West during your vacation?

For any vacation type in key west:.

Ocean Key Resort-A Noble House Resort lets you soak in the island's charm with a barside pool, private cabanas, and uninterrupted views of the Caribbean. Located on Key West's biggest island, it's easy to connect via rental car from Key West International Airport.

Hilton Garden Inn is part of the renowned collection of Keys hotels which features year-round outdoor pools, modern tropical décor, and friendly knowledgeable staff. Consider taking a lyft, uber, or taxi from Key West International Airport to avoid paying parking fees.

For family vacations in Key West:

The Marker Waterfront Resort is one of the newest hotel additions to Key West, providing updated amenities and an intuitive layout. Keyshuttles will transport the whole family from the airport to your hotel's front door from Key West, Fort Lauderdale, or Miami International Airport.

Southernmost Beach Resort on Duval Street is close to boutique shops, art galleries, eclectic restaurants, and non-stop nightlife. Daily bike rentals are also available from several locations to keep your family entertained and active on your Key West getaway.

For romantic vacations in Key West:

Chelsea House Hotel is a quiet historic inn with an acre of botanical gardens so you can travel back in time to the days when Ernest Hemingway called these islands home. The VIP concierge can help guide you towards your best transportation options on the island.

The Gardens Hotel offers intimate cottages with tropical verandahs for a romantic beach vacation in Key West. This hotel is located just 3.7 miles from EYW Airport.

For luxury vacations in Key West:

Crown Plaza Key West-LA Concha is a historical landmark situated on the popular Duval Street. It puts you within easy reach of Key West's most popular shopping district. Key West International Airport is just a few miles away and easily accessible by taxi.

Hyatt Centric Key West Resort and Spa offers sweeping views of the Caribbean, docks, Mallory Square, and the Key West Aquarium. You can easily rent a car at Key West International Airport for added flexibility when travelling around the islands, however Hyatt Centric Key West charges a $20-a-night parking fee for guests.

For budget vacations in Key West:

Fairfield Inn & Suites by Marriott Key West is one of the few hotels that also offers free breakfast with your nightly rate. Easily hop on the trolley which stops in front of the hotel for a new vantage point of the city when traveling between different locations on the island or to Key West International Airport.

Eden House and Suites is a 4-star guest house in the old city that prides itself on old-fashioned customer service coupled with modern comforts to help you find your home away from home. In addition to a heated pool, Eden House also offers guests waterfalls, hammocks, swings, and a garden café on-site.

Where to stay in Key West

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• Fares, Fees & Schedule
• Going to Key West
• Going to Fort Myers Beach
• Going to Marco Island
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Key West Express Ferry to Paradise

Chill out - relax - enjoy - explore.

Our jet powered catamarans whisk you away to Key West from either Fort Myers Beach or seasonally from Marco Island.  THE Vacation Spot of Poets, Pirates, Presidents & Partygoers. 

Get your camera ready and soak in the vibrant arts and entertainment of Duval Street, experience world-renowned deep-sea fishing or SCUBA diving, and don't miss the awe-inspiring daily Sunset Celebration at Mallory Square!

For more information about planning your next trip to Key West and what to expect onboard the Key West Express simply TAP:

• Fares and Schedules
• Frequently Asked Questions
• Things to do and where to stay in Key West

Your Booking Options

INDIVIDUALS

15 or More Passengers

We offer departures from two convenient Southwest Florida locations; Fort Myers Beach (year round) and Marco Island (seasonally) to Key West, Southernmost Point of the United States.

Boarding & Departure Times

• Ft. Myers Beach to Key West :    Boarding begins at 7:00AM. Boarding required no later than 7:30AM. (8:00AM departure)
• Marco Island to Key West :           Boarding begins at 7:00AM. Boarding required no later than 7:30AM. (8:00AM departure)
• Key West to Ft. Myers Beach :    Boarding begins at 5:00PM. Boarding required no later than 5:30PM. (6:00PM departure)
• Key West to Marco Island :           Boarding begins at 4:00PM. Boarding required no later than 4:30PM. (5:00PM departure)

Schedules and times are subject to change. Travel time and actual time on Island varies depending on weather & sea conditions

however, plan on approximately 3.5 hours between ports.  

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 100 Grinnell Street  Key West, FL 33040

  239-463-5733

Fort Myers Beach

 1200 Main Street  Ft. Myers Beach, Florida 33931

Marco Island

 951 Bald Eagle Drive  Marco Island, FL 34145

Flights to Key West (EYW) with American Airlines

Popular flights with american airlines.

Dallas (DFW) to

Philadelphia (PHL) to

Salt Lake City (SLC) to

Providence (PVD) to

Washington, D.C. (DCA) to

Sioux Falls (FSD) to

Charlotte (CLT) to

New Orleans (MSY) to

Savannah (SAV) to

Salisbury / Ocean City (SBY) to

Portland, OR (PDX) to

Tallahassee (TLH) to

Hartford (BDL) to

Oklahoma City (OKC) to

Cleveland (CLE) to

Boston (BOS) to

Norfolk (ORF) to

Knoxville (TYS) to

Allentown (ABE) to

Scranton (AVP) to

*Fares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Some fares listed may include one or more connections that are Basic Economy, which class is subject to additional terms and conditions . Modifying this information may result in a different fare. To find the most updated fare, please visit aa.com. Additional baggage fees and charges for optional products and services may apply.

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Key West routes with American Airlines

• Philadelphia - Key West
• Dallas - Key West
• Salt Lake City - Key West
• Providence - Key West
• Sioux Falls - Key West
• Savannah - Key West
• New Orleans - Key West
• Salisbury / Ocean City - Key West
• Portland, OR - Key West
• Hartford - Key West
• Tallahassee - Key West
• Oklahoma City - Key West
• Norfolk - Key West
• Boston - Key West
• Cleveland - Key West
• Birmingham - Key West
• Miami - Key West
• Chicago - Key West
• Minneapolis - Key West
• Allentown - Key West
• Scranton - Key West
• Milwaukee - Key West
• Los Angeles - Key West
• Ontario - Key West
• Alexandria - Key West
• Wilmington - Key West
• Tulsa - Key West
• Portland, ME - Key West
• Grand Rapids - Key West
• Omaha - Key West
• Buffalo - Key West
• Rochester - Key West
• Tucson - Key West
• Sacramento - Key West
• Las Vegas - Key West
• Reno - Key West
• Fayetteville - Key West
• Gainesville - Key West
• Jacksonville - Key West
• Orlando - Key West
• Pensacola - Key West
• Tampa - Key West
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Painted Canyons Of The West

Enjoy radiant Paris and the Renaissance romance of Florence, dramatic Alpine landscapes and the Eternal City of Rome where you'll toss a coin in the Trevi Fountatin to secure your swift return.

Trek across the Southwest as you take in the sienna-colored canyons, towering spires, and desert landscapes found in Utah's five national parks. The backdrop of Denver's Rocky Mountains is the starting point of your journey. In Colorado's wine country, dine with new friends and enjoy a tasting at a family-run winery. Among vistas that evoke the spirit of the Old West, marvel at the unspoiled beauty of Utah's five national parks. Make your way from Arches and Canyonlands to Capitol Reef, Zion, and Bryce National Park. Discover the bright lights and glitz of Vegas. Explore the kaleidoscope of colors found in America's rocky western landscapes.

Our prices start from

9 Days • GUIDED • 11 Meals

The Details

• 8 nights accommodation
• On some dates additional accommodations may be used
• Services of a tour manager
• All on-tour transportation and related fees
• Hotel-to-hotel baggage handling
• Round trip home to airport sedan service provided when you purchase airfare through Member Choice Vacations. One transfer per person, per reservation. (Restrictions apply)
• 7 breakfasts, 2 lunches, 2 dinners

Engaging Experiences  These special places and experiences are considered tour highlights. Look for them in the daily itineraries.

Sheraton Denver Downtown, Denver, CO or Hilton Garden Inn Downtown, Denver, CO

Trek across the Southwest as you take in the sienna-colored canyons, towering spires and desert landscapes found in Utah's five national parks. Your journey begins in the mile-high city of Denver — an urban gateway to America's natural beauty.

Enjoy dinner and a wine-tasting in Colorado's wine country.

Doubletree Hotel Grand Junction, CO

Breakfast, Dinner Included

The Rocky Mountains are your traveling companions on the drive to Grand Junction. Look out at the natural scenery as you pass by Glenwood Canyon, a product of the Colorado River, carved more than 3 million years ago. Dine together at a family-owned vineyard and enjoy a wine tasting in the midst of Colorado wine country. Today breakfast and dinner will be included.

Element Moab Hotel, Moab, UT

Set out to explore the Colorado National Monument this morning along Rim Rock Drive. Make your way to Utah on the Upper Colorado Byway, known by the locals as "River Road." As the iconic Fisher Towers loom over breathtaking mesas, make your way to Moab, Utah's outdoor adventure center. Today breakfast and dinner will be included.

Behold incredible views at Dead Horse Point State Park in Moab.

Breakfast, Lunch Included

Journey through the otherworldly oases of two national parks. Hike* along red rock features as you make your way through Arches National Park. Continue to Canyonlands National Park, resting in the heart of the Colorado Plateau, and discover a world of mesas and canyons. Close by, at the Island in the Sky, look out over a landscape of ethereal valleys and dreamy horizons. Today's park pilgrimage ends atop the sheer sandstone cliffs of Dead Horse Point State Park. Today breakfast will be included.

*While there is opportunity to hike on this tour, all hiking is elective and should only be undertaken by people who are physically fit and have prior hiking experience, especially at high elevations.

Take in the thrilling and mesmerizing scenery on Utah's most scenic byways.

Best Western Plus Bryce Canyon Grand Hotel, Bryce, UT or Best Western Plus Bryce Canyon Ruby's Inn

Travel through the dramatic Utah desert on Scenic Byway 24. Visit Capitol Reef National Park, named for the curved white walls that resemble the U.S. Capitol building. On the Million Dollar Road, take in views of Grand Staircase-Escalante National Monument, where layers of warm reds and oranges melt into smooth sided peaks. Spend the night in Bryce, your jumping-off point to Bryce Canyon National Park. Today breakfast and lunch will be included.

Explore the amazing spires of Bryce Canyon National Park, known as hoodoos.

Holiday Inn Express, Springdale, UT

Breakfast Included

Spend the day in Bryce Canyon National Park and see the famous hoodoos – vibrant rock formations likened to fairy chimneys. Perhaps you'll start your morning with a hike,* getting up-close and personal with the graceful geology. Take in the sprawling vistas as you walk along Sunset Point, leading into Sunrise Point Rim Trail. As the day draws to a close, settle into Springdale, a small town perched just outside of Zion National Park. Today breakfast will be included.

Climb aboard Zion's open-air tram with a guide.

There are few places on earth that match the beauty of the red and white sandstone cliffs of Zion. Make the most of an entire day exploring this rock-ridden paradise. On Zion's open-air tram, wind along the Virgin River through the 2,400-foot deep, half-mile wide Zion Canyon. Choose how you spend the afternoon because it's your choice! Hike* independently - OR - visit Zion's Human History Museum. Today breakfast will be included.

Paris Hotel, Las Vegas, NV

Age-old nature is replaced with captivating energy, vibrant lights, and endless excitement in Las Vegas. Toast with your travel companions at a farewell lunch. Then, the evening is yours – spend your time along the neon-lit strip however you please. Today breakfast and lunch will be included.

Say goodbye to Las Vegas and the painted canyons of America as you depart for home.

Itinerary featured is for May 2024 – April 2025 tour departures. Departures prior will vary. On some dates alternate hotels may be used. Pricing is per person, double occupancy, land only, based on May 12, 2024 travel date. Single supplement from $1,000. Call AAA for current airfare rates and availability. Airfare to the destination is not included, on-tour flights, when applicable, are included..

All this makes it AAA Vacations ®

AAA Complimentary Inclusion: Up to $50 per person credit toward an optional pre-paid excursion

Member Benefit: $50 per person savings

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Anchorage, Denali National Park, Fairbanks, Talkeetna

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