Celebrate Valentine's Day in Key West (Updated 2026)

Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are the only company offering the Key West Beach Pass....
$107

Key West Sail, Snorkel, Kayak with Sunset Option
Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge....
$105

Key West Backcountry Safari
Spend an unforgettable day sailing emerald waters, kayaking mangrove-shaded channels and snorkeling coral gardens in an unspoiled marine wilderness....
$105

Sunset Sail Cruise in Key West
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's...
$102

Cruise into a stunning Florida Keys sunset aboard a comfortable 53’ catamaran. Your crew will guide you through the waters surrounding Marathon, passing local landmarks...
$102

Embark on a personalized gourmet journey through the lively streets of Key West, where you'll savor a diverse range of street foods from succulent shrimp...
$101

Depart the island of Key West & enjoy a full day of sightseeing along the iconic Overseas Highway! You'll travel halfway up the keys to...
$100

Meet for this Key West Sunset Sail at the Key West Historic Harbor. Board a beautiful bugeye schooner, and get acquainted with your captain and...
$100

The beach pass is an all-day, all-inclusive package. Buy a combo package that includes parasailing or one that includes an umbrella, chairs, and all the...
$100

Key West 4 Seater EZGO Golf Cart Rental
Considering a golf cart rental in Key West? Four adults can zip around the island in style on a 4-seater gas-powered EZGO golf cart, and...
$99

Key West 4 Seater Electric Car Rental
Cruise Key West with family or friends! Four people can get around town in comfort and ease with the smooth, silent GEM 4-seater electric car...
$99

Key West Wind & Wine Sunset Sail
Wind & Wine has been the #1 rated sunset sail on City Helicopter Tours for over a decade. In our opinion, this is the best...
$99

Economical, safe Key West fishing fun. Great inshore fishing with only 9 other guests onboard on our Premium Key West Party Head Boat Fishing Experience....
$99

Afternoon two-tank Key West Scuba dive trips offer divers the chance to explore two different dive sites on the pristine coral reef system of the...
$99

The morning two tank Key West Dive Trips are great because this includes a double dive in a Vandenberg wreck dive....
$99

Shark and Wildlife Viewing Adventure in Key West
This is the only shark tour in the USA and to our knowledge the only tour where guests do not get in the water to...
$99

Board the Dolphin Watch & Snorkel Cruise Key West for a journey to observe the beauty of Key West dolphins....
$99

Go where other tours can’t. Enter historic Fort East Martello after dark, meet Robert the Doll, then stay behind for an extended paranormal investigation inside...
$99

Hemingway Food and Walking Tour
This guided walking tour will take you to the real places that Hemingway lived, worked and played, including where he watched and refereed boxing matches,...
$99

Ready for the most beautiful 2 hours of your Florida Keys vacation? Forget crowded piers and noise—imagine yourself drifting peacefully as the sun melts into...
$99

Florida Keys Jet Ski Rental
Unleash your adventurous spirit with a jet ski rental from Seahorse Water Adventures in Marathon, Florida. Explore stunning coastal views and encounter native wildlife at...
$99

