annapolis maryland travel guide

Annapolis and Anne Arundel County Conference & Visitors Bureau

Top 25 Things To Do In Annapolis

Welcome to the historic city of Annapolis , Maryland! Listed below are the top 25 things to do in the city, according to the many visitors who filter through our Visitors Center each year.

This city is a captivating destination that exudes charm through its history as one of America's oldest cities and former capital of the United States. Its blend of colonial history , maritime heritage , culinary excellence , and art scene captures the hearts of visitors worldwide. While planning your visit to Annapolis, you may have realized there are many things to do and might wonder where to begin. We hope this list inspires you so that you can journey through Annapolis, discovering the past and the present and the beautiful Chesapeake Bay along the way.

an aerial view of historic Annapolis and the Naval Academy Chapel with the Severn River behind it.

U.S. Naval Academy

Armel-Leftwich Visitor Center: 52 King George Street, Annapolis, MD 21402

Founded by George Bancroft in 1845, the United States Naval Academy is home to thousands of midshipmen training to become officers in the U.S. Navy and second lieutenants in the Marine Corps. Filled with immense history and architectural beauty, visitors can tour The Yard by walking or hopping on a five-passenger electric vehicle. The USNA museum is also on-site at Preble Hall, offering two floors of exhibits about the history of seapower and the U.S. Navy.

Maryland State House

100 State Circle, Annapolis, MD 21401

Visit the oldest state capitol in continuous legislative use by walking along the marble corridors where George Washington resigned from the Continental Army and look up at the largest wooden dome constructed without nails in the U.S. Take a self-guided tour to learn about how Annapolis used to be the capital of the U.S. and other facts that may surprise you.

A view of the Maryland State House through an alley

William Paca House & Garden

186 Prince George Street, Annapolis, Annapolis, MD 21401

A National Historic Landmark, the William Paca House offers visitors a glimpse into the wealthy colonial lifestyle that lawyer, governor, and Declaration signer William Paca and his family indulged in. Its Georgian-style architecture and interior have been restored to their original beauty, and guests are invited to tour the lavish home. A 2-acre walled garden is located in the backyard, creating a serene break from the bustling of the city.

a view of a garden at William Paca House and Garden

Trolley Tour with Towne Transport

Depart: 26 West Street, Annapolis, MD 21401

Enjoy a 60-minute tour of historic Annapolis aboard one of Towne Transport’s air-conditioned red trolleys! Along the route, visitors can admire and learn about various century-old Georgian-style homes and other points of interest in Annapolis, like the colonial seaport, state capital, county seat, sailing center, and the home of the United States Naval Academy.

Banneker-Douglass Museum

84 Franklin Street, Annapolis, MD 21401

Operated by the Maryland Commission on African American History and Culture, the Banneker-Douglass Museum is the state's official Museum of African American Heritage. The museum is located in a historic church formally known as Mt. Moriah African Methodist Episcopal Church. Here, visitors are immersed in African American history with its permanent exhibit, “Deep Roots, Rising Waters: A Celebration of African Americans in Maryland,” along with temporary exhibits.

A father and son celebrate Black History month with a visit to the Banneker Douglass Museum.

Kunta Kinte-Alex Haley Memorial

City Dock, Annapolis, MD 21401

Located in City Dock, The Kunta Kinte-Alex Haley Memorial pays tribute to Alex Haley and his ancestor, Kunta Kinte , which Haley had discovered through stories told by his grandparents. Through storytelling, Haley determined that Kinte was a survivor of the slave trade who landed in Annapolis and was sold into slavery at 17. When Haley learned of his history, he wrote the Pulitzer Prize-winning novel Roots, which follows Kinte's journey. Now, a bronze statue of Haley reading his book to children remains as a permanent memorial to commemorate Alex Haley and Kunta Kinte for many years to come.

a sunrise photo of the Kunta Kinte Alex Haley Memorial at Annapolis City Dock

Annapolis Maritime Museum and Park

723 Second Street Annapolis, MD 21403

The Annapolis Maritime Museum is located in a historic water-front oyster packing plant formally known as McNasby Oyster Company . The museum’s mission is to educate and inform visitors about the enormous ecological wealth and history of the Chesapeake Bay through interactive exhibits, environmental programs, camps, and community events.

Boats and oyster dredging tools at the Annapolis Maritime Museum

Thomas Point Shoal Lighthouse

Thomas Point Shoal, Annapolis, MD 21403

This historic lighthouse is situated in the Chesapeake Bay and is the most recognized lighthouse in the state. Constructed in 1875, it is the only screw-pile lighthouse in the bay that stands strongly as a reminder of an old era in maritime history. Visitors can schedule a boat tour to the lighthouse, where they can tour the inside of the structure and learn about the fascinating history of lighthouses and the keepers who lived in them.

Hammond-Harwood House

19 Maryland Avenue, Annapolis, MD 21401

This estate was built for tobacco planter and Anne Arundel native Matthias Hammond, who sold the house to Jeremiah Towne Chase and then passed it to Chase's daughter. The architecture is a five-part Anglo-Palladian mansion that is known to contain some of the best woodcarving and plasterwork in America. Visitors can partake in a guided tour or a self-guided tour through educational exhibits and Hammond-Harwood Garden.

Museum of Historic Annapolis

99 Main Street, Annapolis, MD 21401

This Museum is located steps away from City Dock and introduces visitors to the cities through its current exhibits, Annapolis: An American Story and Summer’s Legacy: Preserving the Beaches, which follow the history and preservation of several historically Black waterfronts.

Museum of Historic Annapolis brick building

Dock Street, Annapolis, MD 21401

City Dock has been an important staple in Annapolis and Chesapeake Bay history for at least 350 years. Today, it is the heart of Annapolis and is home to bay-side restaurants, boat tours, and shopping. Visitors can watch boats slowly turn around at Ego Alley, a narrow waterway in City Dock where boatowners parade their expensive yachts. Conveniently, Main Street is only a few steps away.

Main Street

Main Street, Annapolis, MD 21401

Located in Historic Downtown Annapolis, Main Street is a lively strip that houses an assortment of everything Annapolis has to offer. Lined with well-preserved historic architecture, many shops settle in this sought-after location. There are plenty of shops, restaurants, and art galleries to check out that will satisfy everyone.

Watermark Tours

1 Dock Street, Annapolis, MD 21401

Watermark offers Annapolis visitors an impressive range of boat tours that provide leisure and an intriguing history of Chesapeake Bay. Popular cruises include the Annapolis Harbor & USNA tour, Spa Creek Cruise, Chesapeake Bay Bridge cruise, and more that are suitable for the whole family to enjoy. Watermark’s boats also have a bar serving drinks and light snacks on board, as well as a restroom, and most are handicap-accessible and temperature-controlled.

Reynolds Tavern

7 Church Circle, Annapolis, MD 21401

The Reynolds Tavern is an enchanting building with a rich history that dates back to the 18th century. The building was constructed by hatter and dry goods salesman William Reynolds in 1747. Many businesses have operated inside, but many historic features remain as they were hundreds of years ago. Today, the Tavern is a unique dining experience that offers afternoon English Tea, lunch, dinner, a beer garden, and a full-service pub.

Ghost Tours with Tours & Crawls Annapolis

16 Church Circle, Annapolis, Maryland 21401

Locally owned and operated for over 20 years, Tours & Crawls has been serving visitors and locals with spooky ghost tours that highlight Annapolis' dark history and the many haunted sites that the historic town holds. Take a 90-minute walking tour or join a haunted pub crawl tour offering alcoholic spirits with...spirits. Pub crawl tours visit 3-4 haunted bars, giving visitors 20-30 minutes at each location.

Annapolis Tours & Crawls Ghost Tour gathers in front of a haunted site

Chase-Lloyd House

22 Maryland Avenue, Annapolis, MD 21401

One of the first three-story brick houses to be built in the 13 colonies, the Chase-Lloyd House, was built in 1769 by Samuel Chase , one of the signers of the Declaration of Independence. The house was passed down to a relative named Hester Anne Chase, who then left the house to her nieces, who then turned the home into a home for elderly women in 1888. While the house no longer operates as a living facility, the main floor and garden are available for the public to tour.

Annapolis Symphony Orchestra

801 Chase Street, Annapolis, MD 21401

An anchor in Annapolis for the past 60 years, the Annapolis Symphony Orchestra aims to inspire, educate, and enrich the public by providing extraordinary musical experiences. The orchestra is composed of 70 professional union musicians who perform music for all ages. They also put on an outdoor concert and Quiet Water's Park each summer!

people on a grassy hill in front of an outdoor ampitheatre for a concert

Mission Escape Rooms

40 West Street, Annapolis, MD 21401

Mission Escape Rooms has four different rooms that range in difficulty and are perfect for beginners or experienced problem solvers. Explore their new escape room titled "Battleship," where you and your fellow sailors are under attack and need to defend your ship. There are three other escape rooms titled "The Legend of Sasquatch," "The Bureau.," and "Once Upon a Crime." No matter which room you choose, an unforgettable, puzzling experience awaits.

Mission Escape Rooms - Once Upon a Crime room

Rams Head On Stage

33 West Street, Annapolis, MD 21401

Rams Head On Stage is the top club with under 500 seats in the world! The venue hosts talent from all over the globe, including lots of musical artists from different genres. Rams Head On Stage also has dining options in the venue itself, and the Rams Head Tavern is located directly next to the building. Check out their current calendar of events here.

A black man in a blazer plays a guitar and sings into a microphone

Annapolis Ice Cream Company

196 Main Street, Annapolis, MD 21401

For 19 straight years, the Annapolis Ice Cream Company has consistently won "Best Ice Cream in Annapolis," and their hand-crafted ice cream definitely reflects the award. The store in Annapolis makes its ice cream on-site, creating premium, homemade ice cream using only the finest ingredients.

A boy and his dog sitting on a bench eating ice cream

GameOn Bar+Arcade

144 West St, Annapolis, MD 21401

A newer addition to the city, GameOn is a unique mix of bar and arcade . There are many games to play, including skeeball, giant Jenga, Foosball, and several pinball games. There are also a ton of classic arcade games like PAC-Man and Tetris, as well as more recent games like Fast and Furious and Mortal Kombat 3. Of course, tasty drinks are served from the bar, including their very own 21+ Capri Sun.

An old school arcade with skee ball and stolls

Charles Caroll House

107 Duke of Gloucester Street, Annapolis, MD 21401

Once inhabited by Charles Caroll , signer of the Declaration of Independence and the only Catholic man to do so, the house contains more than 300 years of history and three generations for the public to view. Gain insight on Maryland and American history by partaking in public or private tours that take visitors inside the Caroll's home, as well as their extensive gardens.

a brick house with a white portico porch

Visit Annapolis & Anne Arundel County Visitors Center

26 West Street, Annapolis, MD 21401

Kick off your trip by visiting the Visit Annapolis & Anne Arundel County Visitors Center, where you will be met with knowledgeable information specialists who will guide you through the history of Annapolis and offer recommendations for your itinerary. Conveniently, a visitor center booth at City Dock with the same trained volunteers will assist you in your adventures in Annapolis.

Thurgood Marshall Memorial , Lawyer's Mall

100 State Circle, Annapolis, MD 21401 (outside of the Maryland State House)

Civil rights leader and Maryland Native Thurgood Marshall became the first African-American to serve on the Supreme Court. In his 24 years of service, Marshall is best known for the Brown v. Board of Education case that ended racial segregation in American public schools. This memorial is a stunning tribute to commemorate Marshall's legacy as a lawyer, jurist, and influential leader of the civil rights movement.

For Top Attractions just outside the city in Anne Arundel County, scroll through the blogs below.

23 Sites to See in Anne Arundel County

An aerial shot of a beach with water in the background

Top 15 Things to See and Do in Anne Arundel County

Refind Antiques a small art and antique store in Galesville.

Current Scoop on the Vintage Loop

Galesville Hot Sox courtesy of Galesville Community Center Organization, Inc. Archival Collection

In Southern Anne Arundel County, Galesville Offers Maryland’s Own Field of (Negro League) Dreams

Getting to Know the Benson-Hammond House

Chesapeake Crossroads African American Heritage Trail

A Hidden Arts Gem in Northern Anne Arundel County: Chesapeake Arts Center

A view from the Annapolis harbor to the Chesapeake Bay

Chesapeake Crossroads Heritage Area: Key to Meaningful History

Brandi mckeating, download the free 2024 visitor guide.

This handy resource includes a complete listing of accommodations, restaurants, shopping destinations, and more in Annapolis and Anne Arundel County!

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The Sailing Capital of the U.S. Is a Perfect East Coast Getaway — With Historic Charm, Tasty Seafood, and Scenic Harbor Views

Here’s what you need to know about visiting Annapolis, one of the East Coast’s best waterfront destinations.

Best Things to Do in Annapolis

Annapolis hotels.

Where to Eat and Drink in Annapolis

Best Time to Visit Annapolis

Getting there.

The famous “crab cakes and football” line from “Wedding Crashers” may have firmly planted itself in the cultural zeitgeist 18 years ago, but there’s a lot more to Maryland than seafood and sports (although those are pretty important, too). Given its East Coast location and proximity to the Chesapeake Bay, many of Maryland’s towns and cities have waterfront access — hence, the association with the fishing and crabbing industries as well as sailing and other maritime activities.

As one of the original 13 colonies, Maryland was also influential in the shaping of the United States; in 1791, the state transferred ownership of a portion of its land to the federal government to form the country’s new capital, Washington, D.C.

Sean Pavone/Getty Images

There’s perhaps no city that combines everything Maryland is known for — food, culture, and historical significance — quite like Annapolis. Home to the U.S. Naval Academy, a walkable downtown, and a robust sailing community, the state’s capital is perfect for a long weekend away or an extended visit to the Chesapeake region.

DenisTangneyJr/Getty Images

With a nickname like the "Sailing Capital of the U.S.,” it should come as no surprise that Annapolis plays host to various water-adjacent activities. The warmer months are particularly buzzy around Annapolis Harbor and City Dock, the heart of the historic district.

If you’re visiting for the first time, a guided tour of the city is your best bet to cover as much ground as possible. In true Annapolis fashion, there are plenty of options to see the area by boat. Visitors who come aboard the Harbor Queen will explore Annapolis Harbor and cruise by the banks of the Naval Academy while learning about the city’s history and geography (tours are available from April through October). The Annapolis Maritime Museum & Park also offers Skipjack history tours that provide additional information about the Chesapeake Bay and its ecology. Travelers who don’t quite have their sea legs can opt for a 60-minute trolley tour around the charming streets, marinas, and high points of the city. Access to the U.S. Naval Academy is limited, but it’s certainly a must-see spot when in Annapolis. Both public and private tours can be arranged through the Armel-Leftwich Visitor Center .

SerrNovik/Getty Images

If you prefer to discover a new place on your own, be sure to walk down brick-paved Main Street and pop into its shops, art galleries, restaurants, and bars. One block away, you'll find State Circle and the Maryland State House , the only state house to have served as the nation's capital and the oldest state capital in continuous legislative use. Further out in the Annapolis Design District — about two miles from State Circle — numerous murals decorate the city. From the 7,000-square-foot Breonna Taylor mural (located at 14 Dorsey Avenue) to the Carlester “Walking Man” Smith mural (found at 1100 West Street) that honors a local who spent 40-plus years cleaning up the trash from Annapolis streets, these murals can be appreciated via a self-guided walking tour .

Like the city itself, the best hotels in Annapolis have touches of nautical whimsy and nod to the city’s history. Graduate Annapolis opened in the arts district in 2019 with decor “inspired by Chesapeake blue crabs, Academy colors, and old-school madras plaid.” Like other Graduate hotels, the property proudly celebrates the culture of local colleges — the U.S. Naval Academy and St. John's College. As its name suggests, Annapolis Waterfront Hotel, Autograph Collection , is conveniently located by the harbor, and it’s just a short walk to the Naval Academy. Historic Inns of Annapolis is made up of three landmark buildings in the downtown area: Maryland Inn, Robert Johnson House, and Governor Calvert House. Each house pairs 18th-century details and quaint ambiance with modern amenities (including free Wi-Fi).

Kevin Fleming/Getty Images

Where to Eat and Drink in Annapolis

The culinary scene in Annapolis goes above and beyond seafood — but if you’re visiting Maryland in the summer months, oysters and blue crab should make it into your diet at some point during your trip. For a taste of a traditional Maryland crab house, there’s Cantler’s , Mike’s Crab House , or The Choptank . Chick & Ruth’s has been a city staple since the 1960s, and Iron Rooster has a popular all-day breakfast menu. For a post-dinner sweet treat, head to Annapolis Ice Cream Company , where you can indulge in homemade flavors like Funfetti cheesecake, blueberry strudel, and birthday cake.

If you want a heaping dose of Annapolis history, add Reynolds Tavern and 1747 Pub to your itinerary. You’ll take a step back in time when you enter the tavern for traditional English afternoon tea or the cellar pub (watch out for the low ceilings) for a refreshing Pub Punch or lager. The beer garden behind the tavern also welcomes guests during the spring, summer, and early fall. For something a bit more modern, there’s Preserve for cocktails, Fox’s Den for craft beer and pizza, or Galway Bay Irish Restaurant and Pub , a lively pub on Maryland Avenue.

SeanPavonePhoto/Getty Images

Like most other parts of Maryland, Annapolis is a true four-season destination. The warmer months, however, are ideal for adventuring out on the water. Spring is typically the best time of the year to go to Annapolis, as summer tends to become busier when sailing season kicks into high gear.

Annapolis can easily be explored on foot, but you’ll need a car if you want to venture further into the Chesapeake region. Washington, D.C. and Baltimore are both about an hour’s drive away, depending on traffic, so flying into any of the area’s three international airports — Baltimore-Washington International Thurgood Marshall Airport (BWI), Washington Dulles International Airport (IAD), and Ronald Reagan Washington National Airport (DCA) — puts you within driving distance of Maryland’s capital.

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17 Best Things To Do In Annapolis, Maryland

Including the best things to do in this patriotic town, such as crab cakes, sunset cruises, and history tours.

Learn The Area's History

Get On The Water

Enjoy local cuisine, have an early drink, stay awhile.

Annapolis, Maryland , is not a town to brag—but it could. This coastal gem existed here over a century before 1776, and it can still celebrate with the best of them. While the patriotism runs all year long, every summer you'll find this place fully decked out in red, white, and blue, welcoming visitors with flags waving and young midshipmen walking together on the street. Annapolis has its history down but doesn't stop there. You'll find plenty of character, great crab cakes and local cuisine, and plenty of opportunities to get out on the water too. Settle into a waterfront room and enjoy this walkable city where you can spend the day browsing quaint boutiques or overlooking the harbor.

Here's our guide to the best things to do on your trip to Annapolis, Maryland.

Learn The Area's History

Take a history tour.

The streets of Annapolis hold more than 350 years of American history, and you could spend hours strolling up and down Main Street, where shops, hotels, and restaurants thrive inside 18th-century brick storefronts. City Dock, once a shipping hub, now acts as a host to schooners and other boats waiting to set sail on the Chesapeake Bay. Join a guided tour—such as the Colonial Annapolis Walking Tour or Walking Ghost Tour —to learn about the town's history and lore.

watermarkjourney.com , 1 Dock St Annapolis, MD 21401

toursandcrawls.com , 16 Church Circle, Annapolis, MD 21401

Visit St. Anne's

Up the hill sits St. Anne's Episcopal Church , where engraved Communion silver gifted by King William III in 1696 continues to grace the altar every Sunday. Many of the 24 stained glass windows and mosaic are more than 100 years old.

stannes-annapolis.org , Church Circle, Annapolis, MD 21401

See The Historic Maryland State House

Nearby, you'll see the Maryland State House, which is the first and only one that also served as the U.S. Capitol. It was here that Gen. George Washington resigned as commander in chief of the Continental Army in 1783.

msa.maryland.gov/msa/mdstatehouse/html/home.html , 100 State Circle, Annapolis, MD 21401

Visit The Yard

The United States Naval Academy campus, also called The Yard, sits at the confluence of the Severn River and Chesapeake Bay, just a minute's stroll from Main Street, so it's an easy afternoon activity for those exploring town. It's designed in grand Beaux Arts style, making it an architectural sibling to The Metropolitan Museum of Art in New York City and the Grand Palais in Paris.

Bancroft Hall, the main dormitory, defines the view on campus with its intricately detailed stone facade and almost five miles of hallways. Across the Yard, the copper-domed Naval Academy Chapel occasionally hosts weddings and also houses the crypt of Revolutionary War hero John Paul Jones. In the summer, incoming freshmen, or plebes, begin a rigorous training camp and you may be able to catch one of the plebes' formal parades on Worden Field and schedule a campus tour.

usna.edu/homepage.php , 121 Blake Road, Annapolis, MD 21402

Cruise The Chesapeake Bay

"You probably need to get on a boat." That's what any local will say to an out-of-towner. Known as the Sailing Capital of the U.S., Annapolis can turn even a seasickness-prone passenger into a wannabe sailor with a thirst for wind. First-timers will find no better way to be introduced to the Chesapeake Bay than a cruise with Capt. Jennifer Kaye ("Captain Jen") aboard one of her family's 74-foot wooden schooners, Woodwind and Woodwind II .

Captain Jen started the family business along with her parents nearly 30 years ago, and she and her crew offer daytime and sunset cruises from April through October. Book one of the Wednesday night cruises to participate in Annapolis Yacht Club's summer race series, a season-long tally for bragging rights. "There are not many other places in the country where you can turn off the engine only five minutes off of the dock," Captain Jen points out. "When you're sailing back with the wind as the sun sets over the skyline, it's pretty magical."

If you're used to cruising lakes or rivers on a noisy motorboat, get ready to experience boating in its purest sense. Captain Jen maneuvers her boat in the shadow of the immense Chesapeake Bay Bridge. With a half-turn of the wheel, the wind roars into the sails. If you're lucky enough to visit for the Fourth of July , find a spot on Captain Jen's cruise for the best seat in the house to see the fireworks display on the bay. She warns that tickets sell out as early as January, so don't miss out.

schoonerwoodwind.com , 80 Compromise Street, Annapolis, MD 21401

Go Paddleboarding

If you already have your sea legs, you can charter a fishing boat or rent smaller water vessels like kayaks and stand-up paddleboards to explore the bay. Capital SUP (a local business that offers rentals, tours, and lessons) can get beginners going on the water and moving like pros in no time. They also have lots of handy tips. "Make sure to tap your heels on the paddleboard, or your toes will start to feel numb!" owner Kevin Haigis advises newbies by the dock. Capital SUP even teaches fitness classes such as yoga, Pilates, dance, and boot camp right atop the water. From the looks of the brave souls returning from these unique workouts, planks and push-ups will never be the same.

capitalsup.com , 600 Quiet Waters Park Road, Annapolis, MD 21403

Try Maryland Crab Cakes

The first time you eat a true Maryland crab cake, it will ruin you for all others. You'll immediately see the cracker-packed varieties for what they really are: posers. Maryland crabs aren't a dime a dozen, and the cocky little pinchers know it.

Almost every local can tell you where to go for the " best crab cake in town." (Even if you ask where to find a decent chili dog, they'll still point you to a crab cake.) But where that is always depends on who's talking. Decide for yourself at favorites like Dock Street Bar & Grill and Carrol's Creek Cafe , which serve up area favorites alongside the usual suspects: peel-and-eat shrimp, crab boils, littleneck clams, and rockfish.

dockstreetbar.net , 136 Dock Street, Annapolis, MD 21401

carrolscreek.com , 410 Severn Avenue, Annapolis, MD 21403

Crack Steamed Crabs At Cantler's Riverside Inn

In these parts, summertime is synonymous with big platters of steamed hard shell crabs served with loads of Old Bay Seasoning or J.O. spice and a cold longneck to wash it all down. Get there early to get steamed crabs at Cantler's Riverside Inn . From April to December, local fishermen pull up to their docks to unload their catch directly.

cantlers.com , 458 Forest Beach Road, Annapolis, Maryland 21409

Hang With The Locals At Boatyard Bar And Grill

Locals like Boatyard Bar & Grill for crabcakes, crab soup, lobster rolls, and oyster shooters. Order their specialties online to enjoy anywhere in the U.S.

boatyardbarandgrill.com , Severn Ave. & Fourth St. Annapolis, MD 21403

Dine On Fresh Catch

O'Learys Seafood Restaurant serves up jumbo lump crab cakes, whole fish, steaks, and rockfish. Dine on upscale seafood dishes across the water from historic Annapolis.

olearysseafood.com , 310 Third Street, Annapolis, MD 21403

Have Crab For Breakfast At Iron Rooster

Start your mornings at Iron Rooster , digging into a plate of crab cakes Benedict or a crab omelet. You'll see a steady stream of them leading the charge out of these kitchens, accompanied by just as many mimosas and Bloody Marys, even at half past nine on a balmy Thursday morning.

iron-rooster.com , 12 Market Space, Annapolis, MD 21401

Feast At Miss Shirley's Cafe

House specialties at Miss Shirley's Cafe include Crab Hash and Fried Green Tomato Eggs Benedict. Pair the Maryland crab omelet with a Spicy Shirley, a Bloody Mary with a green tomato and bourbon-infused pickled okra.

missshirleys.com/home , 1 Park Place, Annapolis, MD 21401

Spend Happy Hour At Preserve

Post up at dinner spots like Preserve for happy hour deals. Specializing in pickling and fermented foods, pair rotating seasonal cocktails with Pickle-Brined Fried Oysters or Smoked Fish Dip.

preserve-eats.com , 164 Main Street, Annapolis, MD 21401

Check Out Sailor Oyster Bar

Head to happy hour at Sailor Oyster Bar for the raw bar specialties and cocktails. Stay until you have ordered plenty of local delicacies like a dozen fresh clams, house olives, caviar, and spiced bar nuts.

sailoroysterbar.com , 196 West Street, Annapolis, MD 21401

Sample Wine At Great Frogs Winery

Just a few miles outside downtown Annapolis, you can hone your sommelier skills at Great Frogs winery , run by winemakers Andrea and Nathanael O'Shea and their two scruffy dogs, Scout and Bruno (you'll find them on the O'Sheas' heels at all times). Word on the street says the Great Frogs team has a refined palate—the scruffy pups in particular. The cool tasting room will make even a hotter-than-Sam-Hill summer afternoon feel breezy and bearable. So will the wine flights and complimentary charcuterie plate . "You can't just expect people to come out here and drink all day with no food!" jokes Andrea. Now she's speaking the truth.

greatfrogs.com , 3218 Harness Creek Road, Annapolis, MD 21403

Watch The Sunrise At Annapolis Waterfront Hotel

Located in downtown Annapolis, this is the area’s only waterfront hotel, offering sunset or sunrise views of the Chesapeake Bay and historic downtown. Enjoy a relaxing stay with luxurious room amenities like a clawfoot tub, wet bar, and private balcony.

annapoliswaterfront.com , 80 Compromise Street, Annapolis, MD 21401

Soak In The Charm Of Historic Inns Of Annapolis

Surround yourself with Victorian charm at one of three historic inns downtown: the Governor Calvert House, Robert Johnson Inn, and the Maryland Inn. Located within walking distance of Main Street shops and restaurants, the inns feature period furnishings and modern amenities.

historicinnsofannapolis.com , 58 State Circle, Annapolis, MD 21401

With food, history, water adventures, and small-town cobblestone charm, Annapolis has mastered the whole Southern hospitality thing. Whether you're taking off with girlfriends or enjoying a family vacation, you'll find plenty of reasons to salute this picturesque city on the Chesapeake Bay.

Annapolis Travel Guide

Courtesy of Sean Pavone | Getty Images

Why Go To Annapolis

The moment you enter Historic Annapolis , life seems to slow. It's as if history is yanking at your heels and hindering your pace, so you might pause and absorb the past. Indeed, Queen Anne lent her name to the city way back at the start of the 18th century, and it's retained its courtly status for more than 300 years, attracting visitors to its Colonial architecture and cobblestone walks.

Once known as the "Athens of America," Annapolis has always been a city enriched in its culture and history. From the Maryland State House to the Frederick Douglass Museum and Cultural Center, its intimate port city setting welcomes more than 4 million visitors a year.

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# 3 in Best Places to Visit in Maryland
# 22 in Best Small Towns to Visit in the USA

Best of Annapolis

Best hotels in annapolis.

# 1 in Graduate Annapolis
# 2 in Annapolis Waterfront Hotel, Autograph Collection
# 3 in The Westin Annapolis

Best Things to Do in Annapolis

# 1 in United States Naval Academy
# 2 in Historic Annapolis
# 3 in Banneker-Douglass Museum

Popular Tours

Private and personalized tour of Washington dc

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from $ 367.65

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from $ 76.00

Phantoms of Annapolis Ghost Tour By US Ghost Adventures

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from $ 22.50

Annapolis Travel Tips

Best months to visit.

The best time to visit Annapolis is in the spring when the city is redolent with blossoms and the sailing season is just beginning. But each part of the year has its charms. In summertime, you'll find the harbor teeming with boats and restaurant patios filled with diners. In the fall, the changing trees against the historic homes are postcard-worthy. And in the winter, even when a chilling cold settles in the city, Annapolis still appeals with its glowing storefronts and cozy restaurants.

Weather in Annapolis

Data sourced from the National Climatic Data Center

What You Need to Know

Take to the water Annapolis is sailboat central. Take a cruise with a sailing tour operator or at the very least, book a boat tour of the Annapolis Harbor.

Learn the lingo "Mid" is short for the "midshipmen" over at the U.S. Naval Academy. "Johnnie" is short for the students that are enrolled at the liberal arts St. John's College.

Eat like a native Don't leave without sampling some Maryland blue crab. There's an art to selecting the best steamed crabs, but when in doubt, pick a heavy crab – this signifies a lot of muscle.

How to Save Money in Annapolis

Book a hotel in Parole, Maryland The bed-and-breakfasts in downtown Annapolis are pretty high in price; you can save some cash by booking accommodations less than 4 miles west in the nearby town of Parole, Maryland.

Head to City Dock For cheap entertainment, grab a coffee or an ice cream and walk along the dock, taking in the sights and sounds of Ego Alley .

Cash in on free attractions World-class attractions like the U.S. Naval Academy and St. Anne's Church are absolutely free to enjoy.

What to Eat

Owing to its idyllic perch on the harbor, you might guess that dining in Annapolis would be seafood-heavy. And you'd be right. Steamed crabs, in particular, are one of the city's specialties, and you can try them at any number of restaurants. Mike's Crab House and Cantler's are among some of the old favorites. For ice cream, the Annapolis Ice Cream Company is a popular spot. If you're looking for a wine bar, you might try the well-reviewed Vin 909 Winecafe . Chick & Ruth's Delly is legendary, namely for their "colossal challenges," which involve downing a 6-pound milkshake or munching your way through a 3-pound sandwich.

Getting Around Annapolis

The best way to get around Annapolis is by car. Although Historic Annapolis is small and best explored on foot, the greater Annapolis area requires wheels to see. You can also call a taxi. And although the city does offer bus service, it's really not a convenient or efficient way to explore the city.

The closest major airport is Baltimore/Washington International Thurgood Marshall Airport (BWI) in Baltimore . To traverse the 20-some miles south to downtown Annapolis, you can take a taxi or hire a rental car. The Airport Shuttle also offers service between BWI and Annapolis.

The self-important name, " Ego Alley ," comes from the parade of expensive boats and yachts that glide through the narrow waterway in the harbor.