Plan the Perfect Valentine's Day Date in Key West 2024

Love is most definitely in the air, and there’s nowhere better to be than in Key West to celebrate that joyous feeling that makes life worthwhile. The island offers a bevy of romantic things to do for Valentine’s Day, whether you want a traditional heart-fluttering activity or you want to shake things up a bit this time around. Check out our guide to find a Valentine’s Day date idea that suits you and your better half the best.

Check in at 24 North Hotel in Key West

Enjoy a romantic stay at 24 North Hotel in New Town, Key West. Treat yourself to exceptional amenities, poolside cocktails, complimentary weekend yoga, an on-site Starbucks, and a whole lot more. Our hotel is located at the point of entry to Key West and is convenient to everything in Old Town (via our shuttle - complimentary for guests!). Our Ocean View King Suite is perfect for a romantic couple’s night away, with 575 square feet of living space, beautiful photography, thoughtful furnishings, and breathtaking ocean views. Make yourself feel right at home, here.

Take a Key West Sightseeing Cruise Around Town

This Valentine’s Day, plan a special excursion for your special someone. Our concierge can curate personalized Key West experiences such as spa services, bicycle and scooter rentals, snorkeling and diving, seaplane tours, catamaran sailing, parasailing, deep-sea fishing, and much more.

Glide over the gulf at top speed on a jet ski. 24 North Hotel offers a Jet Ski for Less package which includes a 90-minute guided tour for two and a gift of reef-friendly suntan lotion, SPF lip balm, and a 24 North Hotel wellness kit. Or, cruise around with our Bike Around Key West special offer, which includes two bike rentals per day to explore the island at your leisure. Other fun options include a diving excursion around North America’s only coral barrier reef, and a catamaran sunset sail.

Buy the Perfect Key West Valentine’s Day Gift

Shop Petals & Vine for flowers, places like Kilwins and River Street Sweets for freshly made chocolate, and Rodriguez Cigar Factory for cigars. In lieu of gifts, commemorate the special day by taking pictures in front of the island’s most popular locales. See the most iconic, insta-worthy photo stops in Key West.

Plan a Beach Date

When staying with 24 North Hotel, it’s easy to get to the soft sands of Smathers Beach (pictured above). Just borrow one of our bikes for the short ride south. The largest public beach on the island begins at mile marker zero and stretches along New Town. There’s beach chairs and umbrellas, and paddleboards, catamarans, and volleyball courts available for use.

While the view of the deep blue Florida Straits from the beach is gorgeous, nothing can beat a poolside post at 24 North Hotel with a Toasted Punch. It’s the perfect backdrop for a romantic day with the one you love.

Book a Table for Two at a Romantic Key West Restaurant

Get out on the town for a unique dining experience. The perfect Valentine’s Day spot will have sensational food, with a cozy ambiance to boot. Lucky for us, Key West has quite a few restaurants that measure up. Here are just a few of our favorites.

Try La Trattoria Restaurant for authentic Italian cuisine and their famous martini menu that features nearly 20 options. Their Raspberry Chocolate Bomb martini is the quintessential Valentine’s Day sipper, with raspberry vodka, creme de cacao, and Godiva liqueur. Antonia’s Restaurant is another pick for Italian and Mediterranean dishes, with handmade pastas, local seafood, and a Wine Spectator award-winning wine list.

If you’re a foodie, Little Pearl’s 4-course Chef’s Tasting experience is something you and your partner will remember forever. The intimate eatery is seafood heavy, offering innovative, globally-inspired dishes with a tropical twist. The Chef Tasting courses are always changing, and have included dishes like Wagyu Tartare, Sake Braised Bone in Short Ribs, Shio Koji Tuna, and Pretzel and Gingerbread Pudding in the past. Another excellent seafood choice is Bagatelle.

We’re keeping tabs on special Valentine’s Day 2024 menus. So far, Seven Fish and Martin’s have confirmed special experiences on the 14th. Stay up to date with OpenTable for more Key West Valentine’s Day dinner options.

Book your seating in advance!

End the Night at a Bar to Remember

Dive bars slinging domestics may reign in Key West, but there are quite a few cocktail and wine bars to elevate your experience on Valentine’s Day. For cocktail-forward spots, browse the menus at The Roost, The Little Room Jazz Club, Better than Sex, and Berlin’s. For wine, Wine-O Bar & Lounge, Grand Vin Wine Bar, and Vinos on Duval are all superb options, some of which also include cheese and meat pairings.

Start making your Valentine’s Day plans now and show us how you celebrate your relationship in Key West by sharing a picture with us on Instagram at #TheKeysCollection. And if you don’t already, keep up with us by following the 24 North Hotel Facebook and Instagram.

They say the way to someone's heart is through their stomach, so start the day off right with breakfast at 24 North Hotel. Our Bed & Breakfast Package includes a scrumptious breakfast for only $5.

See what our past guests had to say:

“Valentine's Day Get-Away…Had an all-around great experience…The pool area was amazing..The Toasted Coconut bar was very nice. It was located right at the pool with great food and drinks…we also found out we could hang out at The Gates Hotel and use their pool as well…So it's like getting two hotels for the price of one... Did I mention they have a Starbucks!?!?!?!?!?...I come to Key West a few times a year, and now I know I will be staying at the 24 North Hotel everytime.” - PennyCox2014, TripAdvisor

“We stayed there the week before Christmas for three nights. Rooms were nice..Had a great time on Rum Row with some excellent food and drinks. Shuttle service was good..Would come back for another visit!” - Julianne Pennington, Google

“The hotel is really nice…The beds are clean and comfortable…We stayed on the top floor, facing the ocean. Gorgeous…This hotel and The Gates are like the same big property - and there’s a gorgeous grassy seating area in between that is really inviting. The pool is lovely, and the food at the pool is fantastic! Having breakfast at the pool is a great way to start the day!...Everyone is really nice and I love the laid back, cheery atmosphere of the Florida Keys. I’d love to come back!” - Leah, Google