10 Romantic Things to Do in Key West

Breathtaking sunsets, long walks on the beach, bicycle rides - these are things that are the stuff of Hollywood's most romantic movies. They also happen to be some of the most romantic things to do in Key West. As one of the favorite destinations of the kings of Spain and literary figures like Ernest Hemingway and Tennessee Williams, it is one of the most romantic destinations on earth. After checking into a cozy Key West bed and breakfast, take your sweetheart on a romantic adventure around the city.

Rent bicycles in Old Town

Rent bicycles

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

Key West

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

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

Key West 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

Key West 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

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

Key West picnic

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

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

Key West 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 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.