Key West home tours offer a peek into island lives
By: Author Bonnie Gross
Posted on Last updated: December 6, 2023
One of the great pleasures of visiting Key West is admiring the hundreds of historic homes that have been lovingly preserved and restored.
But few visitors get a peek inside those private homes.
Four weekends a year, however, the owners of some of Key West’s most interesting houses open their doors to visitors on Key West house tours to raise money for historic preservation on the island.
Winter 2023-24 is the 64th year that the non-profit Old Island Restoration Foundation (OIRF) hosted the Key West Home Tours. It is one of the oldest home tours in the country.
Tours are planned for:
- Friday and Saturday, Dec. 29-30, 2023: Home Tours “holiday style,” spotlighting five homes festively dressed for the season, including one with six holiday trees.
- Friday and Saturday, Jan. 12-13, 2024
- Friday and Saturday, Feb. 16-17, 2024
- Friday and Saturday, March 15-16, 2024
Tickets for each tour cost $55 per person ($45 for OIRF members) when purchased in advance through oirf.org/home-tours/ or $60 at the door on tour days. (You get a deal if you buy tickets for all four — $200 for nonmembers; $165 for members.)
All 2024 tours are set for 1-4 p.m., with visitors to travel between homes at their chosen speed via their own transportation. Each month’s tour features a different group of homes and a different experience for participants.
The tours feature houses reflecting the varied tastes and originality of their owners. Some showcase homes have been scrupulously restored. Others have been ingeniously renovated. Many have art collections and antiques.
Key West’s Old Town contains what is believed to be the largest predominantly wooden historic district in the United States with almost 3,000 structures. Many were constructed by shipbuilder-carpenters and cigar manufacturing barons in the 1800s, so the island’s architecture reflects the building styles and cultures of its early inhabitants.
How Key West house tours started
The first home tour was organized in 1960. It cost $2 per person and featured eight homes you could tour in three hours on a single Saturday afternoon. It was a very different era for Key West, according to Jean Shannon, a former board member of the OIRF.
“The Old Island Restoration Foundation was organized by handful of people who were really disappointed with what was happening to the island,” she said. “It was happening all over the United States, and it was called progress. Beautiful historic structures were being torn down.
“The organizers of the foundation realized they were losing their history,” she said. “If they didn’t do something, it would all be gone, replaced by gas stations and car dealerships.”
Shannon said the home tours were more than a fund-raiser: “We were opening people’s eyes to the fact that you could buy one of these homes and you could fix it up and you could save it.”
The appeal of Key West house tours today
Today, while few need to be convinced that Key West homes should be saved, education is still a major part of the tours, Shannon said.
“Once the 20 homes are selected, we research each home. We dig into the historic records and learn the background of each house. We want to give the visitor an idea of the history of island.”
It’s not all about educating visitors, however. It’s also about entertaining them.
“You’re walking through somebody’s home that has all sort of interesting features,” she said. Volunteers are trained to point out details about the antiques, art works and architecture.
Sue Huffaker, a Key West resident for two decades who has attended more Key West Home Tours than she can recall, says that’s her favorite part of the tours – you’re not just seeing houses, in a way you’re also meeting the people who live there.
“It’s a form of voyeurism, I guess,” she said, laughing. “You get to see who people are. You see what’s important to them.
“Everybody puts out their most precious things and you get an insight into the person. This person is really family oriented with pictures everywhere. Or this person is into cooking.”
Her favorite thing, however, is to see the choice of art.
“You won’t see Cezanne or Picassos; many people have work by local artists in their homes and some of it is extraordinary,” she said. “I have found some of my favorite artists through the Key West Home Tours.”
Where does the money raised go?
The people who agree to open their houses for the home tours are motivated by helping to raise funds for historic preservation, Shannon said
The money raised by the home tours is used to make grants to local home owners and non-profits to fix up their buildings in the historic district. OIRF grants have helped preserve the Old City Hall, the Custom House, the Martello forts, the Key West Lighthouse, the Women’s Club, several churches, and more. Recently, grants helped fund repairs to historic buildings after Hurricane Irma damaged many.
The foundation also has preserved and maintains the Oldest House Museum and Gardens, 322 Duval St., which is open to the public to visit and tour.
Recruiting home owners to participate in the tour is an annual challenge. Volunteers who know about an interesting home will reach out to individuals and ask them to be part of the tour. Some years, celebrities such as children’s author Judy Blume have opened their homes.
Purchase tickets here .
Key West Home Tours logistics
Homes may be seen in any order and viewings may be split over two days. Since parking is challenging in Key West, it is best to bicycle or to combine walking with the free Duval Loop Bus. Here’s information and the route of the bus.
Resources for planning a Florida Keys vacation:
- Mile marker guide with dozens of stops to help make the most of your drive south.
- Florida Keys wildlife : Places to see animals
- Tiki bars: Soak up the Keys atmosphere
- 12 great kayak outings in the Keys
- Top 10 pit stops on Overseas Highway
- Best beaches in the Florida Keys
Special places to explore in Key West
- Free things to do in Key West
- Key West on budget : Accommodations, restaurants
- Florida Rambler guide to the Lower Keys
- Key West Butterfly Conservatory : A tranquil stop
- Audubon House , a lovely refuge in Key West
- Historic Key West Seaport
- Historic Key West Cemetery is full of stories
- Fort Zachary Taylor
- Key West chickens
All articles on FloridaRambler.com are original, produced exclusively for our readers and protected by U.S. Copyright law. Any use or re-publication without written permission is against the law.
This page contains affiliate links from which Florida Rambler may earn revenue when a purchase is made. This revenue supports our mission to produce quality content.
The author, Bonnie Gross, travels with her husband David Blasco, discovering off-the-beaten path places to hike, kayak, bike, swim and explore. Florida Rambler was founded in 2010 by Bonnie and fellow journalist Bob Rountree, two long-time Florida residents who have spent decades exploring the Florida outdoors. Their articles have been published in the Sun Sentinel, the Miami Herald, the Orlando Sentinel, The Guardian and Visit Florida.
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Wednesday 22nd of November 2023
My brother-in-law's house was on the tour a few years back. He is a shipbuilder and historical architect. I will be there tomorrow, for the annual Thanksgiving potluck.
Your Guide to a Florida Keys Road Trip: Key Largo to Key West
Posted: April 29, 2023 | Last updated: June 28, 2023
Your road trip guide to the Florida Keys
One of the best state road trips in America has to be the sun-kissed drive from Key Largo to Key West in the Florida Keys. This road, known as the Florida Keys Overseas Highway, takes you through a 125-mile island chain that begins just south of Miami. It hopscotches over 42 bridges and five islands, and has turquoise waters stretching in every direction into the Atlantic Ocean, Florida Bay and Gulf of Mexico.
So if you're looking for the perfect Atlantic Coast road trip or cheap beach vacation , look no further than this road trip guide from Key Largo to Key West. And if you'd rather travel from Key West to Key Largo, rest easy—the route works either way. There are shuttles that run from Key Largo to Key West, but keep in mind, you'd be missing out on all the fun in between.
By the way, once you embark on the Florida Keys Overseas Highway, you'll notice that many sites along the way use mile markers (MM) in their address. We use those mile marker points in this story to help you navigate the drive.
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Mile marker: 108–90
The first of the Florida Keys you'll hit after driving about an hour south from Miami en route from Key Largo to Key West is, well, Key Largo. Often referred to as the Dive Capital of the World, Key Largo includes one must-see stop: John Pennekamp Coral Reef State Park (MM 102.5), the first underwater preserve in the United States.
Experienced and novice snorkelers and SCUBA divers will be enthralled by the teeming marine life that lives just below the water's surface, like parrot fish, barracudas and sea turtles. More experienced divers enjoy exploring the USS Spiegel Grove, one of the largest ships ever intentionally sunk to create an artificial reef where pretty fish can thrive.
Back on dry land, travelers can wander nearly six miles of trails at Dagny Johnson Key Largo Hammock Botanical State Park, home to more than 80 species of plants and animals. You can also peruse the work of local artists at myriad galleries.
Best beach: Cannon Beach, found within John Pennekamp Coral Reef State Park, has shallow waters that are perfect for wading. You may even spot cannons and anchors on the beach that remain from a 1715 Spanish shipwreck.
Where to eat: Dig into the catch of the day at The Fish House, Key Largo Conch House or Snook's Bayside Restaurant & Grand Tiki Bar, some of the best traditional restaurants in the area. If you'd rather turf than surf, check out Jimmy Johnson's Big Chill.
Where to stay: If you can't get enough of the underwater world, stay at Jules' Undersea Lodge , the world's first underwater hotel. If you'd rather keep dry, try the adults-only Bungalows Key Largo .
Mile marker: 90–63
Next up en route from Key Largo to Key West is the fisherman's paradise known as Islamorada. Considered the Sport Fishing Capital of the World, it's where backcountry sport fishing and saltwater fly-fishing got their start. Countless seasoned boat captains are ready for hire to take you out to catch the wahoo, marlin, mahi-mahi and tuna that swim in these waters.
There's an even quirkier way to interact with fish here: hand-feeding the tarpon off the docks of Robbie's Marina (MM 77.5). Since 1976, countless Keys visitors have stopped to feed them, and more than 100 kinds of fish gather at the docks for their daily snacks. Feeding the fishies there is so popular, it's been named the No. 1 activity in all the Florida Keys.
Islamorada is also a terrific spot to kitesurf, stand-up paddleboard, go for a hike or take a bicycle ride. Stop by the Laura Quinn Wild Bird Sanctuary, where injured or displaced birdies now make their homes. Or visit the History of Diving Museum, which boasts one of the world's largest collections of diving helmets.
Best beach: Anne's Beach is popular with families (and dogs) because of its shallow waters and lack of waves. Take a walk along the boardwalk or enjoy a picnic at one of the covered tables.
Where to eat: For a quintessential casual Florida Keys meal, go to the Hungry Tarpon. If you want more elegant fare, make reservations at Chef Michael's for creatively inspired local dishes.
Where to stay: When it's time to lay your head for the night, check in to one of the new oceanfront suites at Cheeca Lodge & Spa , or your own cottage at The Moorings Village & Spa .
Mile marker: 63–40
Marathon is the island chain's top boating destination—and for good reason. The area boasts nearly 2,400 boat slips and plenty of facilities to accommodate sailors passing through. But you don't need your own boat to enjoy Marathon and its waters.
For a truly different experience, hop on over to Cruisin' Tikis and have a floating tiki bar adventure. Sunset, mangrove and harbor cruises are all available, as is a swim-stop cruise for a chance to jump into the water.
While you're here, you should also visit Pigeon Key, an island that is accessible by boat, trolley or walking the 2.2-mile Old Seven Mile Bridge. It has a museum to explore, either on a guided tour or on your own. The Bridge is open for walking, running, bicycling, rollerblading and, of course, watching the killer sunrises and sunsets.
Best beach: Sombrero Beach is one of the prettiest beaches in the Florida Keys—not to mention one of the best beaches in Florida . And it's not just popular with humans; sea turtles nest here between April and October.
Where to eat: For any meal, stop by Castaway, which has been serving guests for more than 70 years. Or make a night of it at Hide Away Café, which has an extensive wine list.
Where to stay: The Faro Blanco Resort & Yacht Club is set on the waterfront and gives you a taste of marina life. Lime Tree Bay Resort on Long Key has spacious townhomes for rent.
The Lower Keys
Mile marker: 40–4
After crossing the Old Seven Mile Bridge out of Marathon, you'll find yourself in the Lower Keys, where natural habitats and wildlife refuges thrive. It's no wonder this part of the Florida Keys is known as the Natural Keys. You might even want to consider taking an electric vehicle on this road trip so you don't disturb the animals.
Your best chance to spot a native Key deer, a subspecies of the Virginia white-tailed deer that somehow made its way south, may be in the National Key Deer Refuge, comprised of 9,200 acres stretching from Bahia Honda Key to Sugarloaf Key on the edge of the Gulf of Mexico. More than 20 endangered and threatened plant and animal species can be found within the refuge. Take a quiet walk at dusk or dawn for your best chance to glimpse a Key deer, or join a ranger-led tour to learn more about the area.
Aside from all the eco-friendly fun, Stock Island is well worth a stop. Their maritime history goes back generations, and the marina is filled with shrimping and fishing boats. Artists have been flocking to Stock Island, too, and share their works in galleries dotted across the small island.
Best beach: The shallow, clear water and white sand at Calusa Beach make it a locals' favorite. The beach is a perfect spot for snorkeling too.
Where to eat: In addition to the freshest of seafood, Big Pine Rooster serves up ribs and a special-recipe meatloaf. Or sip like the locals at No Name Pub, located on Big Pine Key.
Where to stay: Consider the waterfront Sugarloaf Lodge , stay in an Airstream at Big Pine Key Resort or pop a tent on one of the reserved campsites at Bahia Honda State Park.
Mile marker: 4–0
You've made it to the end! Closer to Cuba than Miami, Key West is known for its nightly sunset celebrations, party atmosphere and laissez-faire vibe, but it's really so much more.
If you're a writer or bookworm, you'll certainly want to make plans to visit the Ernest Hemingway Home & Museum, where you should keep an eye out for the famous six-toed cats. Then wander through Key West's Bahama Village, a 12-block area of historic homes and restaurants.
Consider a day trip to Dry Tortugas National Park, about 70 miles west of Key West in the Gulf of Mexico, where you'll find some hidden gems . The island, accessible by boat or seaplane, is popular for snorkeling and feeling like you're on your own private island, not to mention touring the Civil War–era fort.
Best beach: Fort Zachary Taylor Beach—or Fort Zach, as locals call it—predates the Civil War and boasts the island's very best sandy stretch.
Where to eat: No visit to Key West is complete without a meal at Blue Heaven, where you can dine with wandering roosters for breakfast, lunch and dinner. Or snag a spot on the tiny balcony at Santiago's Bodega for tapas and flowing wine.
Where to stay: The boutique Gardens Hotel , the adults-only Kimpton Hotels Ridley House or the new Capitana Key West , to name a few. Wherever you stay, you're sure to find your place in Key West, and it's likely you'll follow so many others' lead and start planning your return visit before you even leave.
Art and history in the Florida Keys
Road-tripping from Key Largo to Key West, it's easy to appreciate all the natural beauty. That said, the Keys aren't just a terrific destination for eco-travelers, but artists and history buffs too.
It's easy for artists to find inspiration throughout the Florida Keys. Fortunately for road-trippers, there are many spots to stop and admire their work. One of the largest artists' communities in the Florida Keys is Stock Island in the Lower Keys, just about three miles from the commercial area of Key West. What was once a shrimping boat marina is now a blend of fishermen and painters, sculptors and other artisans who have created an energetic and supportive community.
For history buffs, in addition to Pigeon Key in Marathon and the Civil War–era Fort Jefferson in Dry Tortugas National Park, other must-stops in Key West include the Audubon House & Tropical Gardens, Harry S. Truman Little White House and the Southernmost Point in the continental United States.
Planning your Florida Keys road trip
Now that you're inspired to hit the road, it's time to start planning. After budgeting for a road trip , your next step is to decide whether you will travel south from Key Largo to Key West, or north from Key West to Key Largo. Or maybe you'll opt for a roundtrip.
If you're starting off in Key Largo, it's important to note that the Florida Keys Overseas Highway begins at the Miami-Dade/Monroe County line. So if you're flying to Florida, Miami International Airport (MIA) is the way to go. If you begin in Key West, the airport (EYW) is on the island.
If you're already driving one of the best road trip cars to get to Florida, you're all set. But if you need a loaner, choose one of the best cars to rent for a road trip . Consider packing these road trip essentials and download some of the best podcasts for road trips to make the miles fly by.
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Horses for Courses: Jason Day leads way in taming difficult Torrey Pines
Horses for courses.
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San Diego and Torrey Pines Golf Course welcome the PGA TOUR for the second week of the West Coast swing.
The Farmers Insurance Open features a full field of 156 players. A host since 1968, the familiar two-course layout will determine the champion. Players will tee it up at the North Course, the easiest of the two daily fee tracks, once in the first two rounds. They will play the other three rounds on the South Course, home of two U.S. Opens this century.
Only two players have won more events and money than Jason Day (+2800) . The winner in 2015 and 2018 (both in playoffs) will look to add to his recent hot streak. The longest track on TOUR (7,765 yards, par 72) and the most difficult non-major challenge has fit the eye of the Australian. Racking up seven top-10 paydays from 10 weekend appearances, he has enough power off the tee plus precision on and around the greens to contend annually. The 2014 runner-up hit the podium again in 2022, falling one shot short of a playoff. Last year, he posted T7, his fifth T16 or better in his last six visits.
Players listed are in the field this week; 2023 season stats.
While not a major championship in name, the South Course provides a major examination. The scoring average has ranked the Farmers as the hardest non-major event in two of the last three seasons. All 14 clubs will be in play this week. It's probably not a coincidence that the top players in this category are also at the top of the BetMGM Sportsbook board this week. There’s length, rough and difficult green complexes, making par a solid score this week.
The South Course has ranked in the top five in this category in three of the last four years. Tight driving conditions, coastal breezes and 4 inches of overseeded rough are the challenges presented off the tee. Less than 55 percent of fairways are found each year. The proximity numbers from the tall grass are frightening. Approaching small greens, only 5,000 square feet on average, not even 66 percent find the putting surfaces from the short grass. Navigating closely mown areas and bushy rough around the green will require creativity and nerves.
While other players entered this week might have accumulated more top finishes, defending champion Max Homa (+1100) thrives at Torrey Pines and in California. Producing six career wins on TOUR, the Californian has claimed four of them in the Golden State. His other two victories, both at the Quail Hollow Club in North Carolina, were on another meaty, tee-to-green grinder. After missing the cut in his first three tries, he has bounced back with Win-MC-T18-T9 in his last four starts. His keys to victory last season included residing in the top 14 of Fairways, GIR, Scrambling and SG: Putting.
In 2022, Luke List (+6600) defeated Will Zalatoris (+5000) in a playoff for his first TOUR victory. The big hitter cashed in his previous four visits, including T10 in the 2021 edition and T12 in 2018. After cashing T25 in defense last year, his streak of making the weekend is now six and counting. The streak of champions to rank in the top 10 of SG: Putting has now reached four consecutive seasons.
Strokes Gained: Putting
From the list above, Homa (win), Bradley (second), Theegala (T4), Ryder (T4), Schauffele (T13) and Suh (T20) all factored last year. I’ll point out that Montgomery was T11 in 2022 and English ran third here at the U.S. Open in 2021.
Getting it close from the rough on approach or around the green doesn’t happen frequently. Also, over the last four years, Approach Putting on the South Course is annually in the top five most difficult. The ability to grind and make putts outside the circle of friendship will go a long way this week. Extra credit for guys who grew up on this style of greens.
Making his 13 th appearance, Keegan Bradley (+3000) has never missed a start and has found the weekend 10 times. Playing the South Course on the weekend in his last six visits, he’s cashed three times in the top five, stacking runner-up dollars last year, the best of the bunch.
Tony Finau (+2800) might be the safest player on the board this week. The big hitter has cashed every year but 2022 from nine visits and has finished T24 or better in ALL of them. His five top-10 paydays have come in the last seven years, including three of the last four.
With top-10 results in four of his last six appearances, 2019 winner Justin Rose (+4500) should draw eyeballs. Posting 21-under in perfect scoring conditions, the Englishman converted his third consecutive top-10 into victory. After missing the cut in defense, he posted T6 in 2022 and T18 last year.
- Collin Morikawa (+1000): T4 here in the 2021 U.S. Open, solo third last year.
- Sungjae Im (+2000): Perfect from five tries including T4-T6 in the last two editions.
- Will Zalatoris (+5000): Cashed P2 and T7 in two of three visits as a professional. Missed the cut last year as his back issues were developing.
- Hideki Matsuyama (+5000): Making the cut in 2024 would run his streak to eight straight. Signing for T9 in 2023 and T3 in 2019 are the highlights from 10 visits.
- Sam Ryder (+10000): The 2023 co-leader after 18, the solo leader after 36 and 54 holes, faded to T4 on Sunday. Cashing T10 in 2021, he’s hit the top 10 twice in three years.
The PGA TOUR is committed to protecting our fans. If you or someone you know has a gambling problem, the National Council on Problem Gambling operates a confidential toll-free hotline that you can reach by phone or text at 1-800-522-4700.