Halloween in Key West (Updated 2026)

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

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention...
$79

Make the most of your Key West water time — our Double Dip Key West Snorkeling Adventure lets you explore the underwater scenery at two...
$80

Set sail from Key West's Historic Seaport for a thrilling dolphin watch and famous Key West sunset sail aboard a luxury catamaran with premium wines...
$90

This Key West experience lets you enjoy all that the island has to offer. Sail on a sleek catamaran along the smooth waters of the...
$169

100% Clear Kayaks: Unlike traditional kayaks, ours are completely see-through. As you paddle, you'll have a front-row seat to the vibrant marine life beneath the...
$89

Discover the flavors of the ocean on this locally guided 3-hour food tour of Key West. Savor maritime history through delicious seafood (or tasty non-seafood...
$94

Embark on a journey like no other. This tour takes guests on an amazing journey from Key West to a secluded sandbar & then to...
$150

Enjoy life like a Key West local with a picnic play day on the calm, clear waters and pure white sands of a Backcountry sandbar...
$120

Hey there, I’m Captain Zak; just a guy with a boat who loves showing off Key West and sharing good times on the water. Whether...
$1,200

Key West Craft Cocktail Crawl
Join us on a sip and stroll through Key West's craftiest bars and hidden local gems enjoying 5 local cocktails & 2 food tastings! Discover the...
$99

Introducing Squid! The quietest experience you will have on a boat while watching dolphins. We worked with David Walworth, an MIT educated Naval Architect and...
$143

Beautiful Key West is surrounded by sparkling blue waters of the Gulf of Mexico, making kayaking and dolphin watching the perfect way to spend a...
$120

Key West Reef Snorkel & Sail Adventure
Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both...
$79

Key West Split Fishing Charter
On a Key West Split Fishing Charter, you save by dividing the charter cost between several people. Book your Key West split-charter fishing trip now...
$200

Key West SNUBA Experience
Go Beyond Snorkeling is the closest you can get to scuba diving without being Dive Certified! Go Beyond Snorkeling into new depths for greater durations where you...
$160

Looe Key Marine Sanctuary is part of the Great Florida Reef, the only coral reef in the continental USA, and the third largest barrier reef...
$569

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

Join us for the ultimate sandbar adventure in Key West. This trip combines the best activities Key West has to offer. We will cruise out...
$161

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern...
$89

The Key West Snorkel & Sunset Sail Rum & Reggae Combo checks your Key West bucket list items with snorkeling, a sunset cruise, and icy...
$60

