Experience the Virgin Islands the way they were meant to be seen, from the deck of a classic wooden sailboat.

Captain Rick grew up sailing on the Maine coast and has been sailing for over 50 yearsHe’s sailed thousands of miles across the Atlantic, around the Caribbean and for the last 16 years he has returned to St John every November for the warm winter.

Whether you’re looking for a relaxing half-day sail around the islands, an adventurous full-day snorkeling trip, a romantic sunset cruise or an intimate sailboat wedding, Cimarron Yacht Charter offers an authentic Caribbean sailing experience you won't find on larger tour boats.

Our two vessels - Cimarron, a stunning 43-foot classic wooden yawl built in 1969 and Grace, an elegant 41-foot Bristol center cockpit cruiser depart daily from Cruz Bay, in the heart of St John.

CIMARRON IS A 43' CLASSIC WOODEN YAWL BUILT IN 1969. Her NAME hails FROM A RIVER IN THE SOUTHWEST UNITED STATES. ASSOCIATED WITH WILD HORSES, AND ALSO WITH RUNAWAY SLAVES — AN INDEPENDENT AND ADVENTUROUS SPIRIt.

Grace is a 41.1’ center cockpit bristol high performance cruiser with distinctive classical styling built by some of New England’s finest craftsmen.

Enjoy the paradise of the Virgin Islands sailing on Cimarron or Grace!

HALF DAY TRIP 3 HRS 500.00 MINIMUM 6 TO 8 PPL 100.00 EA MORNING OR AFTERNOON

SUNSET SAIL 4:30 0R 5:00 TO SUNSET SAME PRICING AS HALF DAY

Full day trips 1100.00 up to 6 ppl 6-8 ppl 185.00 ea 10:00 TO 4:00
                                  
maximum capacity 10 passengers

PRIVATE CHARTERs
full day 1300.00 up to 6 ppl 185.00 ea additional person
half day 700.00 up to 6 ppl 100.00 ea additiomal person

LUXURY full day 1500.00 incudes mimosas fresh fruit platter gourmet lunch and open bar

overnight charters ONE TO THREE NIGHTS (LONGER OPTIONAL) 1400.00per night includes

light breakfast and lunch open bar, snorkel gear UNDER THE GUIDANCE OF A CAPTAIN AND MATE. DINNER ASHORE NOT INCLUDED.

PLEASE REACH OUT WITH ANY QUESTIONS WE ARE ACCOMODATING IF THERE’S ONLY TWO OF YOU LET’S TRY AND ADD YOU TO ANOTHER GROUP

The Caribbean waters surrounding St. John, US Virgin Islands have often been described as a snorkeler's paradise. An unusual shallow depth of only 20-30 feet and crystal clear water, you will soon find out why the water and reef system is a National Monument. Our half and full-day snorkeling trips take you to the places off the beaten path that are not easily accessible on island from the beaches of St. John. During our trips we have encountered many sea turtles, octopus, sea stars, parrotfish and occasionally even dolphins and whales! Customize your adventure with lunch or dinner options like Lovango Beach Club, ZoZo’s Caneel Bay or PizzaPi. Luxury full-day charters available with champagne, advanced notice required to create a custom itinerary with your captain.