Cruise the iridescent waters of Florida Keys coast on a romantic 2-hour sailing trip at sunset. Enjoy the intimate atmosphere of this private sailing trip as you admire Florida Keys sparkling skyline at dusk . Allow your expert sk... More

This 2-hour, customizable day sail allows for you to experience the pristine Florida Keys water upon one of our historic schooners. This trip has a capacity of up to 26 people, and a selection of sodas, beer, and wine are included... More

This day typically lasts about four hours (or can be 8) from the time you leave the marina to the time you get back and may include fueling time. There is no chance to forget anything as you will go out on the same yacht for the o... More

This day typically lasts about four hours (or can be 8) from the time you leave the marina to the time you get back and may include fueling time. There is no chance to forget anything as you will go out on the same yacht for the o... More

Enjoy the day hanging out on our 30 ft Double Deck Slide Boat. Have full access to all of our water toys. Relax and listen to music in the shade. Barbecue lunch or dinner and watch the sunset. Swim off the Slide Boat or relax on o... More

Key West is surrounded by stunning reefs. Tell us what you’d love to see and we’ll create the perfect snorkel adventure, complete with cold beer, wine and soft drinks and healthy snacks. If you’ve been looking for the ultima... More

This day typically lasts about eight hours (or can be 4) from the time you leave the marina to the time you get back and may include fueling time. There is no chance to forget anything as you will go out on the same yacht for the ... More

Cowfish offers a smooth and comfortable ride, versatility, and ample space for 6 or fewer in a small package. Whether you want to lounge on the sandbar, snorkel at your own pace, or enjoy dolphin watching, Cowfish provides a great... More

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 the day, pirate ships from afar often ran aground on Sand Key Reef, nine miles off the southern ... More

This trip takes you and your party, (Up to 26 Guests), on a private sunset sail to enjoy wines from around the world and a variety of beers. You will be sailing on a 65-foot schooner while watching the sunset into the ocean. There... More

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon sun and cool off in the bright aqua waters of the Keys as you snorkel and explore Florida's a... More

We are owner-operated and ensure every detail of your trip is perfect! We work with you ahead of time to determine your goals for the day and make them happen. Our guests almost always say that their trip with us was the highlight... More

This day typically lasts about four hours (or can be 8) from the time you leave Marina to the time you get back and may include fueling time. There is no chance to forget anything as you will go out on the same yacht for the ocean... More

This day typically lasts about four hours (or can be 8) from the time you leave the marina to the time you get back and may include fueling time. There is no chance to forget anything as you will go out on the same yacht for the o... More

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 day is spent exploring Key West’s uninhabited mangrove islands... More