Find Your Perfect St John Sailboat Charter

• LUXURY FULL DAY SAILING CHARTER
  $1500
  

  includes:
  morning mimosas
  fresh tropical fruit platter
  gourmet lunch
  open bar

• PRIVATE CHARTERS

  
  Full Day Sail $1300 (up to 6p) ($185pp additional)
  
  Half Day Sail $700 (up to 6p) ($100pp additional)

• GROUP/SHARED CHARTERS
  
  Full Day Sails
  $1100 (up to 6p) (6-8P $185 each, additional)
  10AM - 4PM
  
  Half-Day Sails
  $500 Minimum (6-8P $185 each, additional)
  3 Hrs Morning or Afternoon
  
  SUNSET SAIL
  $500 MINIMUM (6-8P $185 each, additional)
  4:30 - Sunset
                                    

• OVERNIGHT SAILING CHARTER
  $1400 nightly
  1-3 Nights (Longer Possible)
  
  includes:
  open bar
  light breakfast
  lunch
  snorkel gear and guidance
  
  *Dinner Ashore not included
  

maximum capacity 10 passengers
PLEASE REACH OUT WITH ANY QUESTIONS - WE ❤️ TO ACCOMMODATE

Our Story

Cimarron is a 43' classic wooden yawl built in 1969, a true beauty with soul.
Her name comes from a river in the American Southwest, a word associated with wild horses and runaway slaves seeking freedom. It speaks to an independent, adventurous spirit - exactly what you'll feel when you're aboard.

Grace is a 41' Bristol center-cockpit cruiser built by some of New England's finest craftsmen. She's a high-performance vessel with the kind of classic lines that turn heads in every harbor - proof that speed and elegance can share the same deck.

A St John sailboat charter is the epitome of relaxation.

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.

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.