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Everything you need to know about the Conch Republic. Keep up on local events, nightlife and activities while in Key West.

The Best Things to Do on Valentine's Day in Key West

The Best Things to Do on Valentine's Day in Key West

January 30th, 2022 | Activities

Key West is full to the brim with heart-fluttering activities and Valentine’s Day is the time to treat your sweetheart - or yourself - to something special. So, open your minds, your hearts, and your wallets. Here are the best things to do on Valentine’s Day in Key West.

Go on a Romantic Key West Sunset Cruise

Join Fury for a sail on the beautiful waters of Key West. The Live Music Sunset Sail takes you out for an evening aboard their state-of-the-art catamaran accompanied by a live musician on Valentine’s Day. Enjoy a breathtaking sunset with a kaleidoscope of colors, strawberries, appetizers, and a bevy of boozy beverages like Champagne, wine, and margaritas.

Enjoy an Aperitif at Key West’s Best Cocktail and Wine Bars

Begin your special night, with your special someone, at Key West’s best craft cocktail and wine lounges. Expert mixologists are sure to work their magic on Valentine’s Day, so sidle up to the bar for a drink. Some of our favorite spots are The Roost, Vinos on Duval, and Rum Row, The Gates Hotel’s specialty rum and rum cocktail bar.

Make Reservations at a Romantic Restaurant

Incredible meals are said to be the best way to someone’s heart. Come February 14, enjoy the intimate ambiance and indulgent cuisine at Key West’s most romantic eateries. Top choices include French-Caribbean fare at Café Solé, authentic Italian at La Trattoria, and American seafood dishes at Bagatelle or Nine One Five.


Listen to Live Music at Rum Row

Celebrate Valentine’s Day at The Gates Hotel in New Town with live tunes at Rum Row’s outdoor main stage. Our live music series presents performances al fresco, with specialty rums and rum cocktails available from our exclusive partnership with First Legal Rum Distillery. When hunger hits, satisfy your cravings at The Blind Pig, our onsite food truck serving up tasty tapas inspired by regional cuisine and local ingredients.

Indulge in Decadent Desserts at Better Than Sex

There’s no need to choose between a post-dinner nightcap and a sweet treat - Better Than Sex offers both. The dessert bar in the heart of Old Town features decadent desserts and chocolate and caramel rimmed wine, beer, and house-made cocktails in an intimate speakeasy-like atmosphere. Their tables also have privacy curtains and candlelight to set the mood. Reservations are strongly recommended.


Book a Romantic Retreat at The Gates Hotel

Welcome to a sun-soaked paradise. Key West is a frequent romantic destination for couples with its laid back attitude, beautiful sunsets, and walkable streets to explore as a pair. Stay with us at The Gates Hotel and discover the history and soul of Key West. Our local touches immerse you in the art of island living through design, music, and food and drink. Our poolside King guestroom is the perfect retreat for couples. Enjoy the scene from a cozy terrace with seating. This approximately 300-square-foot room offers a plush king bed, pullout sleeper sofa, and the opportunity to relax outdoors. Plan an intimate vacation at The Gates Hotel for a relaxing addition to your happily ever after.


The Gates Hotel Key West is a Conde Nast award-winning hotel set in New Town that offers shuttle service to and from Old Town. Take a look at our specials.

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