Rent bicycles in Old Town


As one of the most historic areas of Key West, Old Town is filled with classic 19th century architecture that will seem to transport you to the days when Hemingway called the island home. The best way to see the winding streets of Old Town is via bicycle, so grab a rental from Eaton Street Bicycles and start exploring!


Watch the sunset at Mallory Square


Nothing is more quintessentially romantic than watching the sunset, and there's no place better on earth to do it than at Mallory Square in Key West. At the nightly sunset celebration, you can watch local street performers and sip on a glass of wine as you witness the sky turning brilliant colors of red, pink and orange.


Visit Hemingway's house


Literary fans will adore taking a tour of famed novelist Ernest Hemingway's home in Key West - the gardens are some of the most beautiful on the island. The grounds are a popular site for weddings, and host the many descendants of Hemingway's six-toed cat - the gift of a ship captain.


Go sailing


If you're looking for a romantic adventure, nothing beats sailing off the shores of Key West. Take a romantic sunset sail on a private yacht or a tall ship schooner, and get to know one of the most romantic spots on earth from the sea. Floridays also offers fabulous Champagne sunset cruises.


Get his-and-hers massages


After a long day of exploring Key West, what's more romantic (or more well-deserved) than a couples massage? Ask for a recommendation at your bed and breakfast, or get a massage on the beach from Spa al Mare.


Climb to the top of the Key West Lighthouse


It's 88 steps to the top, but the romantic view from the Key West Lighthouse is well worth it. While the height isn't exactly dizzying, it offers a bird’s-eye view of the entire island and the museum features a collection of old photographs from the days when the lighthouse saved many ships from crashing into the reefs.


Picnic on the beach


Nothing says romance like a picnic on the beach! Grab some tasty treats from a local vendor and take a stroll to Fort Zachary Taylor. The Civil War-era fort features one of the island's quietest beaches - perfect for sunset picnics.


Have dinner on Duval Street


If you're looking for a romantic restaurant in Key West, look no further than Duval Street. La Trattoria and Nine One Five are both local favorites. After dinner, head over to Simonton Street for one of the famous desserts at Better Than Sex.


Try your hand at snorkeling


You can't leave Key West without trying snorkeling or scuba diving! Explore the majestic reef and colorful creatures, and even the occasional shipwreck. If you have a chance, don't forget to take a swim with the dolphins.


Share a slice of Key Lime pie


Key West is famous for its Key Lime pie, and no romantic trip would be complete without sharing a slice with your loved one. For the best pie in town, head to Kermit's Key West Key Lime Shoppe.