No two nights ever look the same in Key West, the small island that offers a comprehensive list of evening must-dos. But of course, certain staples should always make it onto your agenda: delicious food, strong drink, a sense of adventure, and most importantly, good company. From start to finishing, here is a perfect night out in Key West.
1. Dinner – They say food feeds the soul. Well, it’s also the perfect start to a long and wild night in Key West. The island offers an endless range of cuisines and restaurants, ranging from fresh-caught seafood to seasonal vegetables bought at the local farmer’s markets. If you’re craving a delicious fish dish with a Mediterranean spin, head to Azur where Chef Drew and Chef Michael give extra flavor to local catches like grouper (pictured above) or yellow tail snapper. For heartier dishes and heafty portions, Abbondanza boasts Italian fare that never strays from grandma’s recipes. Or make your way toward Casa Marina for waterside dining and a to-die-for Pina Colada.
2. Sunset Sail – Make sure you have dinner on the earlier side, as the Wind and Wine Sunset Sail takes off promptly at 7pm from the Westin Marina. The two-hour long boat ride feature a selection of international wine, cheeses, and a friendly three-man staff. Of course, the ocean sunset is the highlight of the ride. It’s safe to say it’s the best sunset in Key West.
3. Cabaret Show – You’ll have to hustle from the boat right to La te Da’s for a hilarious cabaret show starring Randy Roberts. The performer will entertain you as Bette Midler and Cher (among other queer icons), as you laugh your way through a two-drink minimum. Seriously though, is there a better way to work your abs?
4. Bar Hop – Now it’s time to get to know Duval Street, the epicenter for all-things nightlife in Key West. Two of our favorite bars, Aqua and Bourbon Street Pub, serve up the meanest drinks and the best crowds. First check out the former for a contemporary aesthetic and a killer drag stage. Grab a seat at one of the many tables as you enjoy a sassy performance and hospitable company. Then walk just a few buildings over to Bourbon Street Pub, the wildest spot on Duval. Start in the front area, where there is a standard bar and go-go boy stage, before heading to the open back patio for a clothing-optional pool and an outdoor watering hole.
5. Late Night Swim – At this point you’ll probably be slightly buzzed and perhaps with new company. Once you’ve had your bar crawl fill, take the pleasant 10 minute walk to Island House. The gay, clothing-optional resort has a 24-hour restaurant, a bar that’s open until 4am, and an all-night pool, spa, and hot tub awaiting you. Grab one last drink, chat with the sweet (and cute) bartenders, and maybe order some late night eats. Enjoy your food and drink pool-side, or finish it all quickly so you can make a new friend who’s also exploring the resort’s beautifully landscaped, open balconies. Keep in mind there’s always an adventure to find at Island House—the best kind of adventure that is.