Make a Key West Vacation a Valentine He’ll Always Remember

fall key west

This Valentine’s Day, there’s only one thing every man wants: Something to look forward to. Now’s the perfect time to plan a getaway far away from the confines of the same four walls you’ve been staring at for the last year. Recharge, reconnect and rekindle the romance with an unforgettable trip to Key West.

The island not only has a perfect climate, but also boasts a vibrant LGBTQ community, unforgettable scenery and an utterly unique local culture that encourages everyone to “Come as you are.” (So don’t let that quarantine beard hold you back.)


While always a great choice for solo travelers and groups, Key West offers couples plentiful opportunities to craft a custom romantic experience, no matter your taste.

To help heat up your travel plans, we’ve put together some of our favorite suggestions fit for a variety of partners.

Photo by Mike Freas/Florida Keys News Bureau

Something Scenic
The sunshine, sand and surf in Key West are enough to lower anyone’s blood pressure, making the tropical climate ideal for getting your groove back.

Any of Key West’s beaches can be prime for some reading and relaxation, but more outdoors-inclined couples can take advantage of the island’s natural treasures. A day trip to Dry Tortugas National Park, a 100 square-mile park across seven small islands, offers an idyllic escape (and a truly enchanting choice to possibly pop the question). It’s easy to reach via seaplane, just a quick trip 70 miles west. Besides ample opportunity to swim and snorkel, Dry Tortugas is a great spot for nature lovers, features the historic Fort Jefferson and, for those who don’t mind roughing it some, campsites for unforgettable overnight starry skies, free from light pollution.

Travelers with less time to spare can keep it local at the popular destination, Fort Zachary Taylor State Park. As one of the island’s most popular beaches, the serene sands are the perfect place for a picnic. The eponymous Fort Zach is also worth exploring, providing visitors exquisite vistas from atop the ramparts of the Civil War fort.

Get even closer to nature at gay owned and operated Key West Butterfly & Nature Conservatory. Trade glances with resident flamingos, Rhett and Scarlett, and feel your full Disney princess fantasy as brightly colored butterflies flutter and flap all around you.

For dinner with a view, make sure to visit Louie’s Backyard. The waterfront favorite has garnered praise from the likes of Fodor’s and Frommer’s for its innovative cuisine and romantic atmosphere.

An elegantly-plated entree at Café Marquesa

Something Stylish
If art, fashion and culture are more your speed, there’s no shortage of options in Key West. Galleries and shops can be found up and down Duval Street, as well as elsewhere throughout the island. Shopaholics can treat their partners (or themselves) to a sharp new ensemble from Graffitti, Inc., the longest-running, gay owned and operated retail clothing store in Key West. The store sells items featuring exclusive, sexy designs by queer artists, as well as some naughtier merchandise.

Of course, the best part of a new outfit is being seen. A great place to strut your stuff is the recently opened Hugh’s View rooftop venue above the Studios of Key West on the corner of Eaton and Simonton Streets. Keep an eye out for Glow Hours on select Mondays to enjoy stunning sunsets and cash bar. Once you’ve caught an eyeful of one of Key West’s signature sunsets, feast your ears on Jazz in the Gardens of The Gardens Hotel, a New York Times pick for “Prettiest Hotel in Key West.”

For a meal as elegant as the white tablecloth it’s served on, enjoy an exquisite meal from Café Marquesa. The seafood-starring contemporary American cuisine is a delight for the eyes as well as the tastebuds, gorgeously plated and begging to be paired with a fine wine (or dry martini).

Photo by Mike Freas/Florida Keys News Bureau

Something Social
Even a romantic getaway can be better with friends, and nothing better sums up the “close to perfect, far from normal” Key West ethos than the people you’ll meet and forge fast friendships with. Take your arm candy for a spin at any number of drag performances at Aqua, 801, Mangoes and LaTeDa. The backyard bar at Bourbon Street Pub is a great place to rub elbows with the locals, and Island House‘s weekly pool party is a great spot to rub some other parts, if that’s your thing.

The fun isn’t contained to the island, though. Some of the best ways for you and your bae to mix and mingle is aboard any number of Key West’s aquatic adventures. For the guys, the gay owned and operated BluQ is a local institution, offering men-only nude sails, snorkels, paddle boarding and more. (Groups, families and individuals can also book Fish ‘N Chicks for private charters and tours.)

If you’re one of those couples that love making vacation friends, a meal at either Santiago’s Bodega or Café Sole includes not only some of the most beloved dishes on the island, but also some of the most attention-grabbing presentations. Take the flashy Saganaki at Santiago’s Bodega, which is served a la flambé, or the famed hog snapper at Café Sole that’s sure to be a topic of conversation around your table (and those neighboring you).

The pool party at Island House (photo taken, as all photos in this story, before the COVID pandemic was underway)

Something Sexy
With the island’s lax attitude to nudity, sexy isn’t hard to find on Key West. When it comes to you and your companion, though, there are few couples activities better than a massage. Ocean Wellness Spa and Salon offers a bevy of packages combining massage and treatments, including facials, manicures and pedicures.

After indulging in a relaxing spa treatment, share a truly decadent evening at the aptly named Better Than Sex. Whether it lives up to its name or not depends on your personal chemistry, but regardless there’s an undeniable sexuality to the desserts offered here, from the extra helping of entendre in the dishes’ names (Cookie Nookie Pie, Italian Stallion, Between My Red Velvet Sheets Cheesecake) to the sensual speakeasy decor. Even the wine glasses are dipped in dripping chocolate or caramel, which makes for a real treat to share over a smooch.

Just don’t get too full on dessert. Surprise your man with a new toy after dark. Support local business and stock up on some erotic accoutrements at Leathermaster of Key West, a self-described “Toyshop for the Adventurous.” It’ll certainly prove to be a more useful souvenir than another postcard.

And the best part of visiting Key West? No matter which style of getaway you choose (or mix and match) there will be plenty left to explore when you inevitably plan your return.

For the latest health & safety protocols in The Florida Keys, please visit

Published at Thu, 11 Feb 2021 16:00:00 +0000

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