This isn’t a packed tourist boat — it’s a true small-group adventure with a maximum of 6 guests. You’re not watching dolphins from far away; you’re close enough to feel that electric moment when they swim right next to t... More

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 iconic stories behind Key West’s signature drinks, like the Hemingway Daiquiri, and ... More

You will begin this 1 hour and 30 minute guided tour by meeting your tour guide, (who will be wearing a neon green shirt) at Margaritaville. Musician Jimmy Buffett arrived in Key West 50 years ago in 1971. This walking tour will t... More

Florida Keys Fishing Experience for the entire family. Serious fishing serious fun! Located in Marathon Key Florida, Wet Tails Charter will give you the charter fishing experience of a lifetime. It doesn’t matter if you are loo... More

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 the north and south sides of Key West, each offering a unique experience. It’s about an hour ... More

Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start a sail to the Key West living reef where you will see coral and tropical fish. All snorkeling equipment is provided an... More

The Hemingway Experience celebrates Key West’s most infamous author, Ernest “Papa” Hemingway, with a historical walking adventure retracing his steps on a "Bucket List" tour of Old Town. Our 4-hour guided experience stops at... More

The only 2-hour jet ski tour in Key West, covering an action-packed 28-mile loop with stops at 5–6 scenic locations. Ride the newest 2024 Yamaha VX jet skis, built for speed and stability, while our expert guides share history, ... More

Gulfstream Fishing is the longest-running party boat fishing charter in Key West, catching steady loads of reef fish since 1947. Our 58-foot Gulfstream IV carries up to 45 passengers and is inspected twice a year by the U.S. Coast... More

Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico and the Atlantic Ocean meet in a symphony of beauty and tranquility. Your day begins as you board a luxurious catamaran, your vess... More

*Visit Stockislandboatcharters.com for alternate availabilities and pricing.* Embark on a tour through the beautiful Florida Keys mangrove back country. Stop at various sandbars to paddle board, snorkel, or just hang out. Watch fo... More

Billy started his Island Jet Ski Tour in 1992. There are many imitators, but only one Original Island Jet Ski tour! Our guides are licensed and local, so they know the waters surrounding our island like their backyard - because it... More

Historic Schooner. Champagne Sunset Toast. Elegant and Exclusive. Step aboard the historic schooner When And If, commissioned by General George Patton in the late 1930s, and sail into a breathtaking Key West sunset. Raise a champ... More

Make the most of your Key West vacation by exploring the island with Fury’s golf cart rentals. Forget the long walks and drive straight into the adventure! Cruise through the Conch Republic like a local with our gas-powered golf... More

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 can easily and safely breathe underwater without heavy, cumberso... More

Experience Key West like never before on Fury’s 90-Minute Jet Ski Tour! Perfect for adrenaline junkies, this thrilling 28-mile adventure takes you around the island’s stunning coastline, and scenic backcountry. Ride solo or wi... More

Key West is famous for it's sunsets and it doesn't get any better then on an intimate sunset cruise aboard our custom tiki bar boats. You and up to 5 guests will toast the sunset with your favorite libation(BYOB). Tours depart an ... More

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne and indulge your palate while being washed in the colors of the Key West sunset! Incl... More

Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and enjoy an evening snorkel. If you do not feel like getting in the water, no worries, the bar is open! ... More

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 that celebrate the island’s unique mix of Cuban, Caribbean, and Floridian influenc... More