Key West Water Sports Activities

We are the only Kayak business on Stock Island's Gulf side that offers direct access to the Gulf, allowing patrons to witness a stunning sunset without...Read more

Party like a local by visiting one of the Florida Keys' Back Country sand bars. Your knowledgeable captain will choose the optimal location based on conditions, leading you to breathtaking turquoise waters and vivid blue skies. You may be lucky enough to spot rays, turtles, fish, or even dolphins while there! Don't forget your swimsuit,...Read more

Escape to the stunning shallows of Key West on an Adults-Only Champagne Celebration Sunset Cruise, where you can savor Moët & Chandon champagne while admiring the sunset. The tour cost includes house champagne Chandon Brut, 7 varieties of red and white still wines, 3 types of ice-cold beers and a gluten-free Gourmet Cheese Buffet featuring 4...Read more

Don't miss out on one of the best activities Key West has to offer—a half-day sailing tour that takes you through the waters of the Florida Keys. During your cruise, you'll have a chance to kayak in a mangrove eco-system and spot various birds, followed by snorkeling in the crystalline sea. Snacks, beer, wine, and use of...Read more

Observe bottlenose dolphins as they frolic in their natural environment on a Key West dolphin excursion. Afterwards, take a voyage to the backcountry for some exhilarating snorkeling. Hunt for marine creatures and underwater plants like coral formations and more.

We're locals, so our captains are familiar with the waters around Key...Read more

. Soar above the waters of Smathers Beach in Key West, Florida from the safety of a state-of-the-art parasail boat. All crew members are licensed and insured for your...Read more

Witness the renowned sunset over Key West from a 1.5-hour catamaran sail. While you bask in the dusk vistas of the ocean as the sun sets, sip some complimentary wine, champagne, beer, sangria or margaritas on board the vessel. As you cruise across the water, appreciate sights of the island with a chilled beverage in hand — an ideal way to...Read more

Embark on a tranquil 3-hour cruise from Key West and make friends with one of nature's amicable mammals--the dolphin. Gaze at the scenic views while these playful creatures swim alongside your boat, then plunge into the Florida Keys' backcountry waters for snorkeling adventures. Uncover the captivating underwater world and observe a...Read more

Dive Into North America's Sole Existing Coral Reef
Investigate the Reef in Two Distinct Locations
Enjoy the Most Efficient Path to Reach the Reef, Allowing You to Spend Less Time Getting There and More Time...Read more

Witness the beauty of a Key West sunset on board the Sandie...Read more

. Embark on this ultimate Key West island exploration from the sea! With your knowledgeable guide, you will traverse across 26 miles (weather and wind dependent) of tropical waters in the Atlantic Ocean or Gulf of Mexico - or both!

Please Note: The price is per jet ski. When booking, 1 Adult corresponds to 1 jet ski; it is suitable for...Read more

Since 1947, we have been the longest running deep sea fishing charter in Key West, Florida. Our 58-foot boat is inspected twice yearly by the US Coast Guard and is equipped with amenities such as restrooms, a galley serving snacks, and experienced Captains to assist anglers. Get your catch of the day on board our vessel - you can keep them or...Read more

. Experience the tranquil, unruffled waters between Stock Island and Key West for 2 hours with a standup paddleboard rental. Traverse above sea grass and through mangrove passages as you search for fish, birds, sharks, rays, and manatees. This is an ideal activity for individuals of all skill levels. Receive a...Read more

Indulge in a secluded, half day excursion for up to 6 individuals on our modern pontoon boat. Revel in the varied marine habitats and wildlife preserves while taking in the rich variety of aquatic birds and sea creatures. Cruise through meandering mangrove creeks with a kayak or paddleboard then recline on a sandbar or islet. Don't forget to...Read more

Billy initiated the Original Island Jet Ski Tour in 1992. Although there are many copycats, none can match our tour! Our guides are certified and locals, so they have an intimate knowledge of the waters surrounding our island as it is their very own backyard!

The route we take depends on the weather & waves - we adjust our itinerary to...Read more

. Come join us for a snorkeling journey to the only living coral reef in North America! We have some remarkable reefs on both the north and south sides of Key West that provide a distinct experience. It's an hour voyage out to the reef, you will stay there for an hour before we embark on our one-hour trip back to the dock. We offer...Read more

Billy began his Original Island Jet Ski Tour back in 1992. There have been plenty of others that have tried to imitate, but there is only one true original! Our guides are certified and live on the island, so they know these waters like their own backyard - because it really is!

We adjust our tour route based on the weather and waves...Read more