Get ready for the gay Florida Keys road trip of a lifetime. Florida’s Overseas Highway is possibly one of the most iconic roadways in America, if not the world. This 125 mile-long historic roadway, with 42 bridges, including the famous 7-Mile Bridge, takes you from the Mainland U.S. over the Atlantic Ocean and Gulf of Mexico. Believe it or not, there are over 800 keys in total! That’s a lot of keys!
Each of the keys offers a unique experience for every traveler. You can stay in a beautiful and relaxing resort in Key Largo or a hip gay resort in Key West. You can go fishing and snorkeling in Islamorada or relax on the beach in Big Pine Key. There are so many options to choose from when planning the perfect gay Florida Keys road trip.
Plan Your Route
With 125 miles and 800 Florida Keys, planning your route might seem a bit overwhelming. The good news is that there’s one main road from the top of the Florida Keys to the bottom. So you won’t get lost. But knowing where to stop and what to do might be a challenge.
Note that distance and addresses along the Overseas Highway are noted by green mile markers (MM), and by whether they are on the Oceanside or the Gulf side.
To help you plan that perfect gay Florida Keys road trip, I’ve provided a TON of information for you in the content below. I’ve also gathered some info from my friends at The Florida Keys Convention and Visitor’s Bureau to assist!
And if that wasn’t enough, we’ve created an entire OutCoast: Gay Florida Travel page dedicated to The Florida Keys that includes information on landmarks, food, things to go, shopping, gay nightlife, LGBTQ entertainment and much more! Check it out here.
Now back to my gay Florida Keys road trip…
How Gay are the Florida Keys?
There’s no denying that the Florida Keys are gay friendly. Key West is, by far, the friendliest of them all. However, even today’s Key West doesn’t compare to Provincetown or San Francisco on the gay scale.
I’ve heard from friends who are older than I that Key West used to be a gay Mecca. It was the place they would escape to when it was difficult to be out at home. It seems that Key West was once a big gay party town. But with LGBTQ laws changing for the better and inclusion becoming a commonality versus a rarity, Key West is not the hot gay scene that it once was.
Today’s Key West sees people from all over – international travelers, domestic travelers, conservatives, liberals, straights and yes – lots of gays. Key West’s “One Human Family” philosophy has created one of the most integrated and unique communities in the world. All are accepted and welcome in the Keys. “Come as you are!”
Even in the light of change, the Florida Keys (Key West particularly) are still home to hundreds of LGBTQ-owned and supportive businesses. You can learn all about them at the Gay Key West Visitor’s Center. And if you’re in town for Fantasy Fest or Key West Pride, then strap on your leather chaps, spray paint your naked body, and party like a gay in 1999.
Here are a few LGBTQ resources to check out during your gay Florida Keys road trip:
Gay Key West Visitors Center / Key West Business Guild
808 Duval Street
Receive a warm Island welcome with a visit to the Gay Key West Visitor Center. The Center is operated by the Key West Business Guild and has been welcoming LGBT travelers since 1978.
You’ll quickly learn why Key West is a premier destination of LGBT visitors. The Center staff will set you up with a directory of gay friendly Key West businesses. You can also get discount coupons to shops, restaurants, and attractions! Start planning your Key West experience here.
I had the pleasure of meeting Fritzie and team while in town.
In the Keys when the sun goes down, the neon comes on and the volume goes up! There are usually plenty of places to party. However, due to Covid-19 guidelines change fast. Check out websites, social media, or call venues for most current info.
Bourbon St. Pub (724 Duval Street) is currently selling liquor to-go only. The beads, boys, and booze party scene will resume as soon as they get the okay to do so. Keep an eye on their social media for updates.
Learn more about our favorite Keys nightspots and watch for them to re-open here.
Although not identified as a gay event, Fantasy Fest attracts gays from all over the world. Fantasy Fest was created by a group of local business owners who were tired of seeing an empty town in October. A small but over-the-top masquerade party was created to overlap the two weekends closest to Halloween. Its goal was to encourage snowbirds to return earlier. And it worked!
Today, Fantasy Fest has become the premier masking and costuming extravaganza, like nothing else you’ve ever seen. The festival includes more than 60 parties, costumed marches, street fairs, and glamorous balls, as well as the show-stopping Fantasy Fest parade.
As you can imagine, Fantasy Fest is the ideal place for gays to be, well – gay! Masks, sequined, boas, leather – it’s every queen’s dream!
2020 Fantasy Fest has been cancelled due to COVID-19. To learn more about future Fantasy Fest events, click here.
Key West Pride
Organized by the Key West Business Guild, Key West Pride takes place in June along Duval Street. The five-day festival includes a street fair, parade and events throughout the week.
Originally rescheduled to November, Key West Pride has officially been cancelled this year, but plan ahead for June 2nd-6th, 2021.
Where to Stay in the Florida Keys
There are many beautiful places to stay throughout the Florida Keys. With over 800 keys, deciding where to stay might be the biggest decision you make. Hopefully, I can help to narrow your options.
On my three-day gay Florida Keys road trip, I spent one night in Key Largo at Baker’s Cay Resort and two nights in Key West at the popular Alexander’s Guest House. I’ve provided a description and photos of each property below. I’ve also provided a few additional options. For a more robust list, read our article on where to stay in the Florida Keys.
Key Largo: Baker’s Cay Resort
9700 South Overseas Highway, Key Largo
Out of the many places I visited throughout my stay, this property is at the top of my favorite list!
There’s plenty of space to relax at this 13-acre 200 room resort. Unwind from your time on the road with a dip in one of two swimming pools or the private beach. Enjoy sitting by the waterfall grotto or a stroll on the nature trail. Even your four-legged family members will enjoy this oasis with their own doggy tiki huts and chilled water bowls!
Rent a kayak or a paddle board and enjoy the sunset views. Unwind in a hammock along the beach. Or relax in your room and watch the sunset from your balcony.
This beautiful location also has everything needed to host private events, including weddings, either indoors or on their grand lawn. I spoke with the General Manager during my visit and she informed me that gay weddings are very common at their resort. I wasn’t surprised, as I met a few LGTBQ people on site. They’ve also seen an uptick in elopements. Start planning your escape here.
COVID Update: Baker’s Cay Resort is a Hilton brand. Hilton recently rolled out the CleanStay Program to keep guests safe and healthy during the pandemic. When I visited the resort, the hotel was not offering valet parking or room service. Guests were also checked in at the welcome gate versus the front desk to minimize lobby congestion. Bell service was available upon request with door delivery. Please make sure to visit the Baker’s Cay website to stay updated on policies and procedures in preparation for your visit.
My Tip: Reserve a Waterfront Suite for the best experience possible. The views are unmatched! Also, grab a drink and kick up your feet in a waterfront hammock.
Other places to Stay in Key Largo
Key West: Alexander’s Guest House
1118 Fleming Street, Key West
This Bed & Breakfast was another favorite of mine. I didn’t want to leave!
Settle into a tropical retreat at Alexander’s Guesthouse. This lovingly restored 1902 guest house has been providing a welcoming atmosphere for LGBTQ travelers, friends, and allies for 35 years!
Enjoy Alexander’s delightful amenities including a pool, jacuzzi, lobby area with books to read, breakfast and complimentary daily happy hour. All just a short walk from historic Old Town. Guests at this adult property must be at least 21.
Parking is available both in front of the property as well as along side streets.
The Alexander’s team is also known for coordinating beautiful weddings on site or with a sunset sail! Get all the details about this slice of paradise here.
COVID Update: Guests on site are asked to take their temperature upon entry. There is also information at the front desk on where to get tested for COVID-19 if you feel unwell. Guests are also asked to wear masks throughout the property, unless in the pool or in guest rooms. Breakfast is being served a la carte as opposed to their standard buffet set up. Bellman services are still available. If you prefer to not have turn down service, please advise the front desk. I was not aware that this was still being offered and was surprised to return to my room with a made up bed.
My Tips: Nothing beats a nighttime swim in the pool at the Alexander House. The white lights in the pool area make for a beautiful experience in the evening hours. Also, book guest room #10 with the outdoor bed. No worries – you get an indoor bed as well. But in the cooler months, I imagine the outdoor bed is an amazing experience.
Other Places to Stay in Key West
Where to Eat en Route to Key West
I hope you like seafood, because the options are endless in the Florida Keys. The region is known for some of the best fishing in the world, so you can expect lots of local treasures on your place. I’ve highlighted a few of the places I enjoyed below. These are more casual options. If you’re looking for a higher-end experience check out some of the resorts along the way.
Key Largo Conch House
100211 Overseas Highway, MM 100.2
Nestled among tropical foliage is one of Key Largo’s most delicious finds. Be sure to say hello to the resident parrot as you make your way to the verandah or outdoor seating garden.
This family-owned environmentally conscious eatery serves-up homestyle fare for breakfast, lunch, and dinner. Their legendary conch fritters have celebrity status – they’ve been featured on “Emeril’s Florida” and the Travel Channel!
The atmosphere at the Conch House is charming and historic. However, the family-owned eatery is totally modern when it comes to technology and safety. They offer a touchless menu and ample outdoor seating. Find out more about this yummy destination here.
My Tip: Try the Conch House sampler. It’s a great way to taste it all – 2 conch fritters, 2 coconut shrimp, island crab cake, cracked conch and lobster & conch ceviche. I also liked the Island Tropical Seafood. I hear it’s a patron favorite. It’s on the sweeter side, but super tasty!
Key Largo Fisheries
1313 Ocean Bay Drive, Key Largo
Relax as you watch the fishing boats head into the Key Largo marina. This off-the-beaten path venue started generations ago as fish market for locals and restaurants. Now the waterfront Backyard Café is a popular casual spot for off-the boat fresh seafood, sandwiches, cold beverages, and live music.
Before you get back on the road check out the fish market for the freshest local and specialty items. They even sell fresh bait for your own fishing adventures. Check out the market and café’s fresh offerings here.
My Tip: Anything is good here. This restaurant has that old Florida feel that makes you crave fresh seafood and fries. I had the lobster bites. Florida lobster never tasted so good! I also hear that their fried yellowtail is a winner. And the desserts? I avoided them for sugar addict reasons, but they looked AMAZING! If you’re staying in a rental property during your gay Florida Keys road trip, make sure to pick up fresh seafood to-go in the market for dinner.
Robbie’s of Islamorada
77522 Overseas Highway, Islamorada
No trip down the Overseas Highway would be complete without a stop to Robbie’s Marina. This iconic waterside village has been entertaining visitors for generations.
Browse the eclectic open-air market that lines the waterfront. Relax in one of the lounge chairs set up around the property and watch the pelicans and boats come and go. For a uniquely Robbie’s experience feed the enormous tarpon that hang out around the marina.
When you’re ready to feed yourself, head to the Hungry Tarpon Restaurant. This waterside spot serves breakfast, lunch, and dinner. The menu has great options to satisfy everyone including signature Keys dishes like cracked conch and Florida lobster. If you had luck fishing they’ll even cook your catch! Find out all the details about this legendary spot here.
My Tip: Grab your camera for the Tarpon feeding. I captured some amazing images during my visit! As for lunch, I was lucky to get a sampling of fresh tuna that was caught by a local. I also tasted the grilled shrimp tacos. I don’t think I’ve ever been that full!
Where to Eat & Drink in Key West
Welcome to the Keys! Loosen that belt loop, because the testing frenzy has just begun! Of course, Key West also offers a delicious seafood selection. The Conch Republic might be a new favorite. For a gay Florida Keys road trip experience, I’d plan a dinner and show (if available) at La Te Da. The food, entertainment and ambience is top notch. And for breakfast and coffee – no worries! I’ve got you covered. Keep reading.
Cuban Coffee Queen
284 Margaret Street (and three other Key West locations)
Start your morning right with a café con leche or chocolate mocha at this local favorite. As the name implies, the Cuban Coffee Queen is the spot for Cuban coffee and other day-brighteners! Enjoy a smoothie, pastries, and specialty sandwiches served on fresh Cuban bread. You can even pick up some of their delicious roasted coffee beans to take home. Get the details here.
Croissants de France & Le Bistro
816 Duval Street
For a tranquil breakfast or lunch head to the garden of Croissants de France & Le Bistro. This bakery, bistro, and coffee shop has been serving-up highlights including Seafood Eggs Benedict and quiche since 1984. They also offer burgers, seafood, and magnificent desserts. Gain five pounds just by looking at their menu here.
631 Green Street at the Historic Seaport
After one of Key West’s legendary sunsets head to dinner at Conch Republic Seafood. This popular casual spot is nestled in Key West’s Historic Seaport along the bustling marina.
Indulge in a classic cocktail from the full bar. Then dive-into Caribbean-inspired local fare. Specialties include Keys shrimp, conch chowder, and oysters callaloo. Fresh seafood is brought in daily to the restaurants own dock. Check out the Conch Republic’s menu you and live music schedule here.
My Tips: Start with the Conch Chowder, then move on to the Baked Oysters with braised callaloo and parmesan cheese, and finally the Local Snapper Fillet with homemade garlic chimichurri sauce, marinated cherry tomatoes and mashed potatoes. Don’t judge – I was hungry that day!
Azur Key West
425 Grinnell Street
Head to the heart of Old Town for a memorable brunch or dinner experience. Azur features brunch specialties like Key Lime French Toast, crab cakes, frittatas and Benedicts. Satisfy your lunch cravings with Mediterranean-inspired salads and sandwiches.
Dinner features exotic dishes like charred octopus, braised oxtail, and seafood risotto. Local seafood including shrimp and grouper are also stars of the menu. Save room to explore their extensive wine menu and daily dessert creations. Explore Azure here.
My Tip: If you’re looking for indulgent, then go straight to the Key Lime French Toast. I skipped the sweet stuff and opted for something that aligned more with the “this plus-sized girl needs to get through this gay Florida Keys road trip without gaining 20 pounds” mentality. So I selected the Four Cheese & Egg White Frittata paired with avocado, Arugula, Basil Pesto Tomatoes. Yummy, healthy and guilt-free!
First Flight Island Restaurant & Brewery
301 Whitehead Street
For a taste of history head to First Flight. This historic 1927 spot was once home to Pan American World Airways ticket counter. Pan Am planes shuttled mail and travelers between Miami, Key West, and Havana. Now this unique space is home to the First Flight restaurant and the southernmost brewery in the United States.
Indulge in signature appetizers, salads, and staple comfort food of the diverse menu. Enjoy the eclectic environment with multiple bar and dining spaces including a tree-top deck and an open air dining area. Stop by the brewery to sample their fresh new selections and relax among the palms. Plan your First Flight adventure here.
My Tip: First, order a cocktail. They’re delicious! Then order the Brussel sprouts and deviled eggs with jalapeño poppers. I skipped dinner and stuck with the happy hour appetizers. But the main menu also looks divine.
La Te Da
1125 Duval Street
La Te Da is a uniquely Key West experience. Once a private home, this 1892 house has been transformed into one of Key West’s most sophisticated, multi-faceted venues.
The restaurant serves classic and gourmet options for breakfast, lunch, and dinner. With extensive menus for each meal there is something for every diner. At breakfast choose from traditional to interesting Benedicts. Lunch and dinner feature signature French onion soup, salads, fresh seafood, pasta, sandwiches, and exciting chef’s daily creations. Be sure to save room for dessert specials.
Any time of day La Te Da’s terrace bar is a great place for people watching and meeting. The open air spot is a popular local hangout. Early evening’s the lobby piano bar is the place to be for beverages and free live entertainment. In the evening the stars shine above in the upstairs Le Te Da Cabaret. Top notch drag performers bring the stage to life Tuesday through Sunday nights.
Next door the La Te Da hotel offers beautifully updated accommodations and full amenities including a beautiful courtyard pool. Learn more about all La Te Da has to offer here.
My Tip: Truth be told, I didn’t make it to La Te Da during my gay Florida Keys road trip, but I had the pleasure of experiencing this Key West treasure during Christmas two years ago. I remember the food being top notch. And the ambience was very romantic. While I can’t remember what I ate, my guess would be the duck. I do remember having nothing but tasty thoughts.
Margaritaville Bistro 245
245 Front Street in the Margaritaville Resort and Marina
Enjoy a relaxing meal at this casual open-air waterfront restaurant. Take in views of Key West’s Harbor over breakfast, lunch, or dinner. Favorites include sandwiches, salads, steak, and pastas. Many dishes feature fresh, local seafood.
Grab a dink and relax on the Bistro’s deck area. This is a great spot for a drink while observing the Sunset Celebrations at adjacent Mallory Square. Every day hundreds of revelers gather to watch the sun fade away in a dazzling spectacle. It’s like Times Square on New Year’s Eve but with palm trees and rum. Adding to the bustle are vendors, buskers, and musicians making for a lively scene.
Find out more about Margaritaville including the Bistro menu here.
Things to Do en Route to Key West
While you might be itching to get to Key West on your gay Florida Keys road trip, stop to savor all that the Florida Keys have to offer along the way. Remember – there are 800 keys! Think of your drive to Key West as foreplay leading up to the main event. Yes…I just compared a road trip to sex. Analogies are my speciality.
Shopping along the Overseas Highway
Shopping in the Keys is not your typical day at the mall. Boutiques, eclectic shopping centers, art galleries, and even clothing stores all offer an air conditioned excuse to stretch your legs and get in a little retail therapy.
No trip to the Florida Keys would be complete without a stop to Shell World (97600 Overseas Highway, Key Largo). This friendly and well-organized gift shop has a great selection of quality souvenirs, home décor, and oh, of course, natural seashells.
Among visitor favorites is the Lobster Trap Art Gift Shop and Gallery (82200 Overseas Highway, Islamorada). This is the spot for nautical-theme art and authentic wooden lobster trap frames. They also specialize in one-of-a-kind artwork, jewelry, and housewares crafted by locals.
Need to update your Keys wardrobe? Bayshore Clothing (8911 Overseas Highway, Marathon) has clothing and accessories for everyone. From swimwear, outfits for the kiddos, and even a “Big Guys” section, the whole family will be comfy and stylish for the rest of your time in the Keys and beyond.
For uniquely Keys creations check out Uniques by Kennedy Studios (8903 Overseas Highway, Marathon). This shop is one of the middle-keys best kept secrets for locally created artwork and handicrafts. They also have a nice selection of clothing, fashion accessories, and jewelry.
Tour the Turtle Hospital
2396 Overseas Highway, Marathon
In the Keys you’re never far away from nature, especially the sea, and the creatures that call it home. The good folks at the nonprofit Turtle Hospital have been taking care of Florida’s sea turtles since 1986. In addition to healing and rehabilitating loggerheads and their marine cousins, the Hospital offers educational programs and tours. Learn more and schedule your visit to meet the resident turtles here.
With over 200 miles of waterfront and easy access to the Atlantic Ocean and Florida Bay the Florida Keys are prime fishing territory. Whether your casting for dinner or the thrill of sport fishing you will come away with great Florida fish tales and possibly a fresh catch!
Start planning your Florida Keys fishing adventures here.
Take a break from the road with stops at some of the beaches off the Overseas Highway. The Keys offer miles of waterfront, but not as many beaches as you might think. Due to the rocky shoreline in many areas, beachfront property is at a premium. Stop to enjoy the beauty and swim your cares away as you make your way south to Key West. We’ve created this list of top Florida Keys beaches to help you plan your time on the sand and in the surf.
Things to do in Key West
You’ve finally arrived at the southernmost point of the United States! Key West is one of my favorite places in the world. Yes, we could recommend having your selfie taken at the giant buoy that represents the Southernmost Point, and you should, but there are so many other things to see and do. So, we’ll skip that highlight. But you should get some sleep, because you’re about to have some fun. On second thought – read this first!
Fury Commotion on the Ocean Sunset Sail
631 Greene Street, Key West
Set sail off into one of Key West’s legendary sunsets. The Fury Commotion on the Ocean 65-foot catamaran makes the perfect backdrop for a beautiful evening. Local musicians provide the soundtrack for making new memories in the waters off Key West. Guests enjoy complimentary libations and appetizers during the two hour excursion. Book your cruise to paradise here.
Seems the gays love a sunset sail!
COVID Update: At this time, the Fury Commotion is taking precautions to keep everyone safe and healthy. They are limiting boat capacity to 25-50% and have made adjustments to the bar and food area so that people keep their distance. Still, be aware that if it rains, EVERYONE gathers under cover. So bring your mask!
Tennessee Williams Museum
513 Truman Avenue, Key West
Key West has been home to many artists and writers over the years. Author and playwright Tennessee Williams made Key West his permanent home in 1949 and lived on the Island with his partner until his death in 1983. Fans can tour this entertaining and informative exhibit honoring his life and career. Check out Williams’ typewriter, other personal items, and view some of the paintings he created.
Insider Tip: In March, Key West honors Williams with a birthday celebration over several weeks. The party includes productions of his plays and other fun. Learn more about Williams’ legacy here.
The Key West Butterfly & Nature Conservatory
1316 Duval Street, Key West
Nature and photography lovers will love the Key West Butterfly and Nature Conservancy. This eye-catching attraction features tropical gardens, cascading waterfalls, a greenhouse, over 20 species of birds, and of course butterflies!
Learn more about these beautiful winged creatures in the on-site butterfly museum and learning center. Get all the details for your visit here.
My Tip: It’s a bit warm in the butterfly garden so dress accordingly. And bring your camera! The photos opps are incredible!
Ernest Hemingway Home and Museum
907 Whitehead Street, Key West
In 1931 Key West captured the hearts of author Ernest Hemingway and his wife. Today their Island home is a National Historical Landmark.
Hemingway wrote many of his classic books in the studio of this tropical oasis. Tour the rooms and beautiful gardens. Be sure to check out the in-ground swimming pool. In 1938 it was the first one on the Island!
Animal lovers will enjoy seeing the descendants of Hemingway’s six-toed pet cats that have full run of the house and grounds. Learn more about this iconic author and his home here.
My Tip: If you are allergic to cats, either stay away or pre-party with allergy meds. I can’t remember how many cats I saw, but they are everywhere. They’re so cute you’ll want to pet them all! And you can!
Kayaking with Key West Eco Tours
5 Geiger Road, Key West
Explore Key West’s natural wonders with a personalized kayak tour. The seasoned guides of Key West Eco Tours will customize a tour to match your interests. Get up close to the island’s lush mangroves, colorful gardens, and the creatures that call them home. Reserve your kayak experience here.
Snorkel excursion with Sebago Watersports
205 Eilzabeth Street, Key West
Head out beneath the waves and experience the beauty of Key West’s underwater treasures. The expert crew at Sebago Watersports will take you seven miles out into the shallow waters of the Caribbean. They provide all the equipment and instruction you need to snorkel like a pro. Float effortlessly above North America’s only living coral reef. Check out the colorful marine life. Climb back on board to relax during your sail back to the island. Explore all your undersea adventure options here.
My Tip: Let go!! Just float and enjoy all that you encounter under the water. I had the most magical experience when I saw two large stingray dancing below the surface. I didn’t even have my camera – I was just one with nature and living in the moment.
Wander the Town
Sometimes the best journeys are the unplanned ones. Enjoy Key West! Wander the town and have fun. Take selfies and photos. And take in all this amazing Florida key has to offer. Here are some of my goofiest moments during my recent gay Florida Keys road trip.
As the Florida Keys reopen information is frequently being updated to best meet the needs of the community and ensure safety for residents and visitors.
During this unusual time please travel safe. Check with your hosts, restaurants, and other venues in advance to learn their current plans and regulations. For updated information check the Monroe County website.
Plan Your Road Trip to the Florida Keys
Exhausted yet? I was! The Florida Keys offer a relaxing, fun and beautiful vacation experience. To plan your gay Florida road trip to the Florida Keys, click here.