Key West is full to the brim with heart-fluttering activities and Valentine’s Day is the time to treat your sweetheart - and 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 Catamaran 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 live music 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 (try their bourbon-based Bless Your Heart cocktail), Vinos on Duval (for sparkling, white, rosé, red, and dessert wines by the glass), and Rum Row, The Gates Hotel’s specialty rum and rum cocktail bar.

Rum Row is part of Rooster Row’s All-Day Happy Hour on Feb. 14. Patrons can visit select bars along the popular path in New Town for all-day Happy Hour savings: Barefoot Bar & Brew (12 - 2 p.m.), Toasted Coconut (2 - 4 p.m.), Rum Row (4 - 6 p.m.), Salty Lime ( 6 - 8 p.m.), and Republica Bar & Lounge (8 - 10 p.m.).

[The Best Cocktails for Key West Sunset Sipping]

Plan a Picnic for Two

This Valentine’s Day, picnic with your love on the Sunset Green Event Lawn, just steps from your hotel room. The Gates Hotel presents a very special Valentine’s Package which includes reserved seating on the green, a Valentine’s card and two roses, a cheese and charcuterie platter, and one bottle of red, white, or sparkling wine. Email amspringer@thekeyscollection.com to reserve your spot.

Make Reservations at a Romantic Restaurant

Incredible meals are said to be the best way to someone’s heart. Come Feb. 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 and Nine One Five. Check out our Key West Dining Guide for more inspiration.

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. This Feb. 10 - 19, the dessert bar has special Valentine’s desserts planned. Reservations are strongly recommended.

Book a Romantic Retreat at The Gates Hotel

Welcome to 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 Suite is the perfect retreat for couples. Enjoy the scene from a cozy terrace with seating. The 300-square-foot room offers a plush king bed, pullout sleeper sofa, and the opportunity to relax in the sunshine just outside your room. Plan an intimate vacation at The Gates Hotel for a relaxing addition to your happily ever after.

[How to Fly Direct to Key West]

Speaking of paradise, The Gates Hotel’s Sunset Green Event Lawn is hosting a very special pre-show celebrating Jimmy Buffett and the Coral Reefer Band’s performances next week at the Coffee Butler Amphitheater. Join us from 1 - 4 p.m. on Feb. 9 and Feb. 11 for ‘Cheeseburger in Paradise’ for live music and fun. It’s always 5 o’clock here!

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, including special rates for seniors, Florida residents, and a Bed & Breakfast package that gets everyone on your reservation a daily delicious breakfast.

We’re proud to announce that The Gates Hotel has been nominated to the Travel + Leisure World’s Best Award 2023! You can vote here.

Looking for more things to do during your Valentine’s visit to Key West? Check out these brand new recurring events at The Gates Hotel, including a Paint & Sip on Feb. 9 and Na Ma Sit and Stay Puppy Yoga on Feb. 12 - just bring your own mat and your pup!