St. John Sailing

St. John Sailing


Pepper is a one-of-a-kind wooden sloop, modeled after traditional Caribbean fishing vessels of long ago. She was built right on St. John, and sets sail from Coral Bay. Pepper has a wide open cockpit with plenty of comfortable seating. If you are looking for an authentic St. John sailing experience, Pepper is the boat for you!

Two Trips Daily

Our day trip is a fun sailing experience that includes a guided snorkel at one of our favorite snorkel spots, and a gourmet lunch on the boat. Our cocktail cruise is a shorter sail during the sunset hours that includes appetizers and drinks. Enjoy great views and learn about the island from your experienced hosts, Lance & Kim. Custom trips are also available.

Superb Snorkeling

We take you to one of St. John's best snorkel spots, and lead you on a beautiful and educational snorkel. We'll identify fish and coral, and point out things you may have missed snorkeling on your own. Captain Lance takes photos along the way, and we'll post them on our social media sites for you to see & share!