The Florida Keys is one of the most queer friendly destinations in the United States. Key West was one of the first cities in the U.S. to elect an out, gay mayor. And that’s just scratching the surface of the iarea’s queer inclusiveness. Naturally, it’s also one of the reasons jumped at the opportunity when the Florida Keys & Key West Tourism Council invited me to fly down and experience my own lesbian Florida Keys road trip with one of my besties Alysse. While I’ve learned a lot traveling in anti-LGBT destinations there is something special about spending time in one that has always celebrated inclusivity and truly lives by the “One Human Family” motto. With its inclusive community atmosphere and relaxed island lifestyle, a lesbian Key West road trip was just the adventure my queer heart was craving.
Live the Island Life
I stayed at Baker’s Cay Resort, which is a beautiful 13-acre hotel with every comfort I could ask for. They even make sure your pets are happy with dog tiki huts and cooled water bowls :: heavy sigh:: my little doxie would have been in her sun worshiper glory.
I loved sitting on the beachside while sipping coffee or eating tacos. I don’t love spicy things but everyone around me was raving about the housemade hot sauce made from peppers grown on the property. My favorite thing was walking down their winding nature trail lined with hidden beaches.
Alexander’s Guest House was another amazing place to stay. This three-story house is a restored Key West “conch house,” built in 1902, and featured tropical decor. There was such a welcoming and comfortable atmosphere. It’s right in the heart of Key West’s Old Town on a quiet, tree-lined street and even has its original pine floors.
Eat Like an Islander
There are two things that stand out at every meal in Key West. The first is the emphasis on fresh ingredients, especially seafood. The second is that almost every table comes with a great view. From fresh fish to the famous Key Lime Pie, I did not have a single bad meal during my visit.
The Fish House
The Fish House is perfect for trying local seafood. The atmosphere here is relaxed and I got to choose between dishes like Mahi Mahi and yellowtail snapper.
Robbie’s Marina was another spot I loved but to be honest even with several restaurants, including the delicious Hungry Tarpon to choose from, the food is not the most memorable thing about Robbie’s Marina. The title goes to feeding the huge, local tarpoons smaller fish while laying flat on my stomach leaning over the edge of the dock.
Chef Michael’s in Islamadora offered an extensive variety of freshly-caught fish, like hogfish and lionfish, and a whole menu inspired by Florida Keys cuisine.
Mrs. Mac’s Kitchen
Mrs. Mac’s Kitchen was an unforgettable meal and is a favorite of locals and tourists alike. The whole place is decorated with license plates that were donated by guests over the years.
I loved trying the Mediterranean specialties at Azur Restaurant. They serve brunch and lunch options like Key Lime Pie French Toast and Monte Cristo sandwiches. Dinner was exotic dishes like pulpo, charred confit octopus, and branzino.
Red Shoe Island Bistro
Red Shoe Island Bistro is a really cool option serving creative combinations like lobster crepes, shrimp mango toast and my favorite the deviled eggs with scallops.
Latitudes is perched on the exclusive Sunset Key Island and dinner came with stunning views of the Gulf of Mexico. Their menu is innovative yet simple and features fresh, local produce and of course plenty of fish.
Caffeinate Before Your Adventure
I’m only ready for a full day of island life or really any other version of life after a cup of coffee. Cuban Coffee Queen put some pep in my step with a decadent Cuban chocolate mocha latte.
This cafe also serves classic items like café con Leche. I loved my egg, sausage, and cheese dish which was perfectly pressed between two slices of crisp Cuban bread.
Play and Snorkel by the Sea
It would be impossible to visit the Keys and not spend time in the water. We chose three separate activities to try, two I’m very familiar with and one (jet skis) that was totally new to me. What better way to kick it off than visiting a woman-owned establishment?
Islander Girl Snorkel and Tours is owned and operated by a mother-daughter team, both of whom grew up diving and snorkeling in the Florida Keys. They guided me to some of the healthiest and most pristine living coral reefs in the world.
Next up was kayaking, with Get Up And Go Kayaking. I’ve been kayaking before but being able to experience gliding over the water and through mangroves in a completely clear kayak was like unlocking an entirely new experience. I can’t recommend it enough.
Barefoot Billy’s was the last stop on the mini water sports tour. I had a chance to explore the island on a jet ski and even see some dolphins. They also offer snorkeling, sunset cruises, and rentals to get around the island.
Tour a Brewery
I’m not a huge beer drinker but Florida Keys Brewing Co made a great case for trying to change my mind. Touring their facility is fun as it’s a beautiful space sprawling with trees and nature. I couldn’t think of a better way to sit back and enjoy one of their beers brewed with local flavors like Key lime, local honey, and citrus.
Explore the New Seven Mile Bridge
The Seven Mile Bridge is one of the most visually iconic landmarks in the Florida Keys, so I couldn’t miss it. Anyone can bicycle, walk, run, or rollerblade along the 2.2-mile-long bridge that parallels the Florida Keys Overseas Highway in the Middle Keys.
I chose to walk so I could fully take in the gorgeous setting. This historic bridge was originally built as the centerpiece of railroad magnate Henry Flagler’s Florida Keys Over-Sea Railroad. This railroad connected the Keys and mainland Florida for the first time!
Take a Sunset Tour
No trip to an island is complete without taking a sunset tour, and the one I took with Sebago Water Sports was everything I was looking for. The Key West Sunset Tour was in a spacious and state-of-the-art ship and the crew was professional and friendly. They made the tour feel personalized and were always engaging. They also offer sailing tours on catamarans and schooners, snorkel and kayak tours, and parasailing.
Take a Historic Tour of Key West
Key West is the center of rich history and architecture on the islands. I couldn’t leave without taking a tour that highlights the best of it. The Conch Tour Train was a lively, narrated tour of historic venues throughout Key West all while riding a cute train.
Celebrate Iconic Famous Figures
Key West has long been thought of as a place of refuge for creativity, so it’s no wonder that people like Ernest Hemingway and Tennessee Williams made homes here. I couldn’t miss seeing Ernest Hemingway’s Home, one of the most famous spots in all of Key West. He spent 10 years writing on the island and even used it as a location for his novel “To Have And Have Not.” I took a tour of the historic home and even got to see a few of the cats that famously surround the property.
The Tennessee Williams Museum tour was also informative and I left knowing much more about this iconic playwright than I had before. You can take a self-guided tour or a curator-led tour.
Step Out Into Nature
The Key West Butterfly and Nature Conservatory was exactly what I needed for a quiet break. I wandered through hundreds of beautiful butterflies while enjoying the cascading, flowering plants.
Visit a Historic Lighthouse
There’s something magical about a lighthouse, and the Key West Lighthouse and Keeper’s Quarters are no exception. First built in 1848, this lighthouse underwent many upgrades over the years and is now a standing museum about the island’s maritime heritage. I also learned all about the brave men and women who kept the light burning through war and weather threats.
I was thrilled to learn that the lighthouse’s first Keeper was a woman! I got a chance to walk to the top of the light and learn all about the Keepers and their way of life.
Lesbian Key West Island Experience
I was so happy to find some amazing spots on the island that celebrate the queer and lesbian community. In TOUCH Key West is the self-proclaimed “gayest, most fun store in Key West, Florida.”
The boutique is a combination of classy, tacky, and fun. I picked up some great gifts. Their unique greeting cards, collectibles, and works from local artists are fun to look through.
La Te Da is a hotel with several bars and is a Key West landmark. I loved their piano bar and couldn’t say no to staying for their nightly cabaret show. Mingling with the friendly staff and lively hotel guests and locals made plenty of fun, new memories.
Planning a Lesbian Florida Keys Trip and More
This island chain had the perfect blend of island living, history, fantastic food, and queer culture making for a perfect lesbian Key West experience. I’ve fallen in love with many cities in Florida but Key West has found its way near the very top!