We hope you will join us as we sail into history!

Day Sail/Snorkel Trip

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This is a private trip for up to 6 guests. Have the Pepper and her crew all to yourselves. Perfect for couples or families to make memories to last a lifetime! Your captain and crew will guide you on a fun and exciting sailing adventure. We’ll glide by beautiful and sensitive natural area historic landmarks. We can drop anchor and explore a nearby island or go for a swim or snorkel over a reef that’s teaming with tropical fish. Afterward we’ll serve you complimentary soft drinks, water, juice, and snacks.

Reservations required.


Sunset Sail

A one and a half hour trip for up to 6 guests
Enjoy the fresh breeze and the local sights as we chase the setting sun. We’ll serve complimentary beer, wine, soft drinks, water, and snacks as we sail our way into the end of the day!

Private Lessons

Wouldn’t you like to say that you sailed a replica of a classic Caribbean sloop on one of the most beautiful sailing grounds on the planet?

Take sailing lessons from Captain Rob, an experienced watersports instructor, U.S. Coast Guard licensed master captain and winner of the Washington’s Birthday Classic Boat Regatta on Florida’s Biscayne Bay.

Captain Rob can teach you the difference between a leech and a luff, a tiller and a turnbuckle, and how to tack and jibe. You’ll learn important safety skills and how to use the wind to your advantage to get to where you want to go.

By the end of your lesson, you’ll have learned basic skills that you can build on during your next lesson or at your home sailing center! We’ll be sure to take some photos of you sailing the Pepper that you can share with family and friends at home.

Note — Private sailing lessons are designed for individuals or small groups that are already comfortable being on a boat. The Captain reserves the right to alter the lesson or turn it into a private charter with verbal sailing instructions based on weather and water conditions and the skill level of the student.

Special Events

Proposing to that special someone? Want a longer trip to a more distant destination?
Contact us to put together the sailing adventure of your dreams.

Whether you are looking for a longer trip to a more distant destination or you’d like to propose to that special someone, we can customize a day trip to fit your needs!
Contact us to put together the sailing adventure of your dreams.

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