Queer Fun in the Sun for a Key West Couple’s Weekend

For some LGBTQ travelers, a Key West vacation might bring to mind non-stop partying and bar hopping until the wee hours of the morning—more of a spring break type fest than a true vacation. But for queer couples looking for a more grown-up vacation, with some relaxation and some adventure, this island treasure still has a lot to offer.

For our first adventure, my partner and I decided to get in the water a bit. We booked the two-hour Island Jet Ski Tour from Barefoot Billy’s, looking to try something new for both of us. The tour begins and ends at the Casa Marina Resort. I drove the Yamaha Waverunner while Lance sat behind me, holding on for dear life. Although there was some choppy water in the Atlantic at the outset, our guide expertly guided us how to deal with the waves, and also gave us plenty of space to play when we wanted to crank up the speed a bit.

Over the course of the 27-mile ride, we saw Key West from every angle, helping us put things in perspective, and where different attractions were in relation to each other. We saw the Southernmost point, glamorous Sunset Key, the harbor, many resorts, and plenty of birdlife around the stunning Caribbean waters. We stopped for about 15 minutes at a particularly shallow and flat spot, where the guide let everyone play around with the wave runners a bit, trying some sharp turns and quick accelerations.

Once back on land, we decided to hit up some of the surprising number of museums and attractions that tiny Key West has.

The Ernest Hemingway Home and Museum, located in Old Town, is the former home of the famed American author. Hemingway lived in this lovely Spanish Colonial mansion for a decade, and tours recount his sometimes soap-opera style life. Descendants of his famous polydactyl (six-toed cats) still live here—dozens of them, in fact (not a great discovery for someone like me who’s allergic!). The cats truly live the life are cared for full time by the staff and a local vet. It’s sort of a quirky local landmark, and if you have time, you should stop and see it once.

Not far away is the Harry S. Truman Little White House, the state’s only presidential museum. Built in 1890 by the U.S. Navy, the 8,700 square foot house eventually became a favorite getaway of President Truman, who spent 175 days there over six years. The facility has served as a Presidential getaway for six U.S. Presidents, and exudes a graceful charm that we were really drawn to. Tours are offered every 15 minutes.

The next day, we continued our explorations. Our only disappointment over the weekend was the Key West Aquarium; the facility felt dated and needs a major refurbishment. That said, if you’re traveling with little ones (I’d say 10 or younger), this might well be preferred to doing the historical museum track.

The far better option for wildlife fans, in my opinion, is the Key West Butterfly and Nature Conservatory. This small but lovely facility is right on Duval Street, and has fascinating exhibits on the life and development of butterflies. There’s a glass-enclosed habitat to walk through, and the 50+ species of butterflies that live here will be all around you. There are also several species of birds here, and the whole tropical setting is divine. While a typical museum gift shop is one of the last places I’d recommend, the gift shop here has some amazing art and butterfly-inspired gifts—enough to make even Mariah Carey blush!

One of our highlights was Danger Charters’ Wind & Wine Sunset Sail. We’re wine aficionados, and we were pretty impressed with the quality of wines they had aboard. We made a bunch of friends on the cruise and enjoyed a lot of wine and some very tasty appetizers, like Caprese skewers and smoked gouda and summer sausage. The staff was a joy to interact with, and we were sad to disembark at the end of the sailing.

We did get in one seriously gay event, the Cabaret at LaTeDah—make sure to get your tickets early. We saw the amazing female impersonator Christopher Peterson, who made his way through a variety of performers, including Marilyn Monroe, Reba McEntire, Joan Rivers, Cher, Bette Midler, Lady Gaga and Tina Turner. Even more impressive, he stayed on stage for the costume and wig changes, making the transformations all that more impressive.