Book an unforgettable crewed yacht charter vacation.

View Available Yachts:

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.

crewed catamaran charters


Catamarans offer stability and space, providing an excellent charter vacation platform. The accommodations are separated fore and aft and between hulls. The cockpit is wide and comfortable for dining with family and friends. Many catamarans feature a flybridge level, great for additional lounging and viewing.
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crewed sailboat charter


Monohulls offer a traditional sailing experience for active sailors. Monohulls are available in various sizes for various budgets and are generally ideal for smaller parties. They heel under sail and offer all the action of a true sailing vessel. Sail the Caribbean Tradewinds.
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crewed power yacht charter

Power Yachts

For the ultimate experience in luxury and comfort, a power yacht or super yacht offers a high crew to guest ratio, individually designed capacious interiors, highly customized, professionally prepared menus and the option to head to your next destination swiftly and style.
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Experience the vacation of a lifetime aboard a luxury, all-inclusive, professionally crewed charter catamaran, sailing, or power yacht in the Caribbean.

Specials and Last Minute Discounts:

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.

See all of the current crewed yacht charter specials and discounts.

Save 15% off new reservations of 5 nights or longer sailing the Virgin Islands from Red Hook during available dates in April - May 2019
Offer Dates:
23 Apr 2019 - 23 May 2019
Confirm before 9 May 2019 Expires in 44 Days
Special offer for new reservations sailing the BVIs:
2 guests: $30,000 for 7 nights
3 to 8 guests: $32,500 7 nights
Offer Dates:
Now - 12 May 2019
Confirm before 31 Mar 2019 Expires in 5 Days
Save 20% off the regular weekly rate through 4 April 2019 or 15% off 5 April 2019 through 15 November 2019. Applies to new reservations 6 nights or longer.
Offer Dates:
Now - 15 Nov 2019
Confirm before 18 Oct 2019

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.


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

> See all of our crewed yacht charter reviews

Caribbean Yacht Charter Vacations

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.