Book with the Caribbean specialists. For over 14 years we have been a leading yacht charter brokerage connecting groups like yours with the best crewed yachts available for charter in the Caribbean including the Virgin Islands & BVIs, Leewards, Grenadines and Bahamas.
Utilize out firsthand knowledge about available charter yachts, crews and locations to book the best yacht and crew for your budget and travel style.
Start planning your vacation today!
Sail away to white sand beaches, consistent Caribbean trade winds, clear blue water, sheltered island bays great for cruising, world-class dive sites, award winning yachts and crew, and sunshine every day of the year.
These crewed catamaran specials are available for new reservations sailing from Tortola or St Thomas in the Virgin Islands or elsewhere in the Caribbean. Contact us now for further information and a no-obligation quote.
We all had the most incredible time.
We have nothing but praise for "Shawtumn". They're an amazing team - we always felt so well looked after. Autumn is an amazing cook. Always kept us on time so we didn't have to worry about anything. They read our group well and suggested excursions were always appreciated. I don't have any captains to compare Shawn to, but he seems to really know what he's doing and we all felt very safe. And added bonus - they're very fun to be around!
Pelican is very clean. A/C kept us comfortable at night. So many good places for lounging above deck.
The pre-cruise preference list was very helpful. The meals kept getting better and better. So impressive that Autumn can make that magic happen in such a small space.
Sailing Directions has great service, emails were always rapidly answered.
THANK YOU FOR THIS AMAZING EXPERIENCE!
Rosa M, aboard Catamaran Pelican, March 2019 sailing the Virgin Islands
The crew were excellent. Everything on board was great. We particularly enjoyed all the branding with logos on everything, made it very professional. Food was spectacular and well presented. The menu was customized to our preferences.
David C, aboard Catamaran Hypnautic, March 2019 sailing the Virgin Islands
Terry and Ruth were both amazing. They are delightfully friendly and good humored, exceptionally knowledgeable about all aspects of the charter experience, and very attentive to each guest. Ruth accommodated one couple’s special dietary needs superbly and without drawing attention to it.
The Big Dog was in excellent condition inside and out. The yacht was clean, neat, well-organized and very ship-shape. Very nice that the guest cabins are air conditioned. She sailed well and comfortably and is very well outfitted. We used the kayaks, paddle board and float numerous times.
Ruth is a master chef! Meal after meal she prepared and served outstanding cuisine, and Terry always found the perfect cocktails and wines to go with each. It was like going to a five star restaurant three times a day!
Great itinerary hitting all the destinations we sought. Terry is very knowledgeable about the islands, history, must-see sights and best anchorages, and he and Ruth have developed great contacts on each island for local transportation, shopping and restaurants.
Sailing Directions provided excellent and professional service and was easy to work with. The website was detailed, well organized and informative.
This charter far exceeded our high expectations. Terry and Ruth are outstanding professionals and we recommend them without reservation.
Eric S, aboard Catamaran The Big Dog, February 2019 sailing the British Virgin Islands
A crewed Caribbean yacht charter offers you the freedom to explore this tropical paradise without limits and at your own pace.
With accommodation, a professional captain, a personal chef, all meals, cocktails, wine, beer, snacks, fuel, equipment, and water toys included, few other vacations offer such an extraordinary experience and value.
Itineraries are completely flexible within your cruising area. Sail the diverse US and British Virgin Islands, the undeveloped and resort islands of the Caribbean Grenadines, or charter a luxury power yacht to cruise St. Martin, St. Barts, and Antigua in the Caribbean Leeward Islands.
Sailing Direction's charter brokers help you book a private crewed yacht in the Caribbean for any group size and budget. Whether you're looking for a family sailing vacation, a couple's adventure holiday, a BVI yacht charter, or a honeymoon or anniversary celebration - we've got you covered for an unforgettable crewed yacht charter experience.