Drenched in history, nestled in pristine water and framed by turquoise skies, Key West has been a favorite destination for centuries. But the popular south Florida town isn’t just about partying on Duval Street. The lush locale with its vivid orchid tree blooms is a particularly beautiful place to celebrate that all-important lover’s holiday―Valentine’s Day. To get you started in the right direction, we’ve put together an itinerary that will ensure your trip is a romantic success.

Getting There

Set the mood on the Key West Express. “What’s more romantic than breathing in the fresh salt air and being in the middle of the ocean,” fleet representative Linda Miller asks. Cuddle up in a roomy booth in the air-conditioned interior, or stroll the bow to watch frolicking dolphins. The sundeck is perfect for a return ride champagne toast.  

Getting Around

Though visiting couples often walk the mile-wide business strip with arms wrapped passionately around each other, faster transportation is a moped for two. Visit the inviting Ernest Hemmingway Home & Museum to see how the infamous author lived, or roam through treasures and tragedies at the Shipwreck Museum to get a deeper sense of days gone by.

Where to Stay

Revered for its impeccable amenities and nostalgic charm, the Southernmost Beach Resort is steps away from the historic district and is an ideal romantic getaway. Enjoy a leisurely breakfast on a private balcony boasting breathtaking blue-water views. Follow it with a quiet morning at the pool. Further soak in the scenery by arranging a luxurious couples’ massage in the oceanside cabana.

Where to Dine

Dining is nothing to take lightly in Key West. With a host of tantalizing menus and intriguing settings, even those with the most refined palettes will find something here to enjoy.

Directly across from Mallory Square, the Roof Top Café offers an expansive outdoor deck cradled amongst the tree tops. “It’s like being in an elegant treehouse,” visitor April Cosimano recalls of her outdoor dining experience. The venue offers savory “new-island” dishes like sea scallops topped with Key lime butter. Sip a refreshing citrus martini while the sound from local musicians drifts softly up from the street corner on a tropical breeze.

For couples seeking a more exclusive dining experience, book a private beach-front table at the Little Palm Island Resort & Spa. This opulent experience provides an unobstructed view of Key West’s stunning sunsets, coupled with an award-winning 7-course menu paired perfectly with your favorite wines.

Wherever you dine, be sure to save room for Key West’s singular dessert-only restaurant, just a few blocks off Duval Street. Better Than Sex has been tempting couples since 2008 with a provocative menu featuring decadent items such as Tongue Bath Truffle, Morning After and the signature Better Than Sex dish, which manager Tia Marquinez describes as a “mix between a bread pudding, a cake and a brownie” baked with three irresistible chocolates, complete with a side of white chocolate mousse. The flirtatious setting heightens the mood with only 15 intimate tables, low lighting and boudoir inspired décor that evokes playful passion. “I really enjoyed the champagne glass with the chocolate and sugar rim,” Key West visitor Ashley Rivas says of the Sex Appeal drink she ordered. “The dim lighting, candles, and the naughty games at the table made our overall experience very enjoyable and satisfying!”

Night Life

No trip to Key West would be complete without a stop at Mallory Square for the nightly Sunset Celebration ritual. Peruse the work of local artists and enjoy daring performances back-dropped by an array of brilliant pink, purple and orange for those last lingering minutes of the day.

When darkness falls, adventurous couples visit Aqua Night Club, enjoying nightly tongue-in-cheek drag-show performances and quality celebrity impersonations. Come in for the laughs and stay for the dancing―this is one sexy venue you won’t quickly forget!

Written by Reneé Novelle, an author and journalist residing in Southwest Florida.

Key West at a Glance

• Key West Express 888-539-2628, seakeywestexpress.com
• The Ernest Hemmingway Home & Museum 305-294-2755, hemingwayhome.com
• Key West Shipwreck Treasure Museum 305-292-8990, keywestshipwreck.com
• Southernmost Beach Resort 888-354-4455, southernmostbeachresort.com
• Roof Top Café 305-294-2042, rooftopcafekeywest.com
• Little Palm Island Resort & Spa 305-872-2524, littlepalmisland.com
• Better Than Sex 305-296-8102, betterthansexkeywest.com
• Mallory Square mallorysquare.com
• Aqua Key West 305-294-0555, aquakeywest.com