Halloween in Key West (Updated 2026)

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

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

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

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

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

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

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

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

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

Discover the flavors of paradise on our Key West food tour through the colorful streets of Old Town. Guided by locals, you’ll enjoy 5+ tastings...
$108

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne...
$109

Avoid the crowded big boats. Trips on this Sailing Catamaran are 1/2 full maximum! Book with a 2 week cancelation policy from vender, and there’s...
$109

Get out to the Key West barrier coral reef in style on a former luxury sailing catamaran yacht now licensed for 30 passengers, but with...
$109

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This...
$109

Key West Schooner Backcountry Eco-Tour
Set sail from Historic Seaport on the Key West Schooner Backcountry Eco-Tour adventure!...
$110

Discover the charm of Marathon, FL, with a delightful Sandbar Experience and Sightseeing Cruise. Enjoy a 4-hour adventure exploring the local scenery on a comfortable...
$114

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in...
$116

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of...
$117

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your...
$119

See more and spend less with a Go City All-Inclusive Pass - the best Miami pass for flexibility and savings. Enjoy unlimited access to 25+...
$119

