Celebrate Your Love in Paradise: 7 romantic things to do in Key West

Key West, the southernmost point in the United States, has long been known as a gay getaway and is even considered by many to be the original gay vacation spot. It is an island paradise located in the Gulf of Mexico, perfect for a romantic vacation this Valentine’s Day. 

Key West is full of amazing things to see and do, but we have picked out some of our favorite romantic activities.

Liquid lunch at Latitudes on Sunset Key 

Enjoy romantic cocktails on a private island 500 yards off the coast of Key West overlooking the Gulf of Mexico where tiki torches illuminate the night sky magnifying the glorious Key West sunsets.

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Cocktails at Latitudes

Climb the Key West Lighthouse

If you’re up for a climb, you’ll be rewarded with stunning views of Key West and the ocean. The Key West Lighthouse was built in 1825 to help the many ships entering the port avoid the hazardous reefs. Today, you can climb the 88 iron steps to the top of the tower for a scenic look at what the lighthouse keepers watched over for more than 120 years.

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Enjoy dessert at Better Than Sex Dessert Restaurant

This famous dessert bar offers an extensive menu of decadent treats in a dimly lit, intimate space. Reservations are definitely required. 

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Take a sunset cruise with fine wines 

A sunset cruise is a Key West classic, so why not do it right on the last boat built in Key West: the luxury catamaran Argo Navis? Fine wines, craft beers, artisan cheeses and charcuterie, and small-batch chocolates are the perfect accompaniment to the natural spectacle.

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Enjoy a sunset bike ride to Ft Zachary Taylor Park

Widely considered the best beach in Key West, Ft Zachary Taylor Park is a National Historic Landmark that played a significant role in Florida’s early development. Follow the path all the way down to the rock jetty… most of the gays will be there! 

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Relax and unwind with a couples massage at “The Top Spa”

Rejuvenate and find serenity at the highest point in Key West. Perched among the clouds high above the island, the beautiful panoramic views and floor to ceiling windows will take your breath away. 

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The Top Spa

Enjoy cigars and whisky in a plush leather lounger 

The picturesque harbor views and comfortable yet classic furnishings at Berlin’s (upstairs at A&B Lobster) creates the perfect atmosphere for winding down a romantic night. Nowhere else on the island will you find a better place to sample a rare cigar, sip a fine cognac, and spend quality time together.

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Get naked with your lover during one of Island House’s two weekly Hot Naked Pool Parties

Strip down to whatever is most comfortable, sip on signature cocktail specials, and enjoy free shots from friendly naked pool boys! These men-only pool parties are legendary and great for making new friends.

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Book your romantic getaway to Key West now and be sure to stay at the famous Island House Resort. Island House benefits from an amazing location and offers gorgeous rooms, a stunning pool, a gym, a hot tub and an award winning cafe! Island House is gay owned and operated since 1976, and that helps to make sure that your needs are anticipated, not just met. 

Visit to book your stay now! 


BWM Staff

Our Staff Writing Team works hard to bring you great content and share news & events from the bear community and beyond.