Book an unforgettable crewed yacht charter vacation.

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Book with the Caribbean specialists. For over 20 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 / USVIs, 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

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

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 charter specials are available for new reservations sailing from St Thomas or Tortola 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.

Catamaran Karma
Catamaran Karma
Ivan and Marisia were ... friendly, knowledgeable, attentive and accommodating” They could not have been more friendly and supportive of us for every minute we were with them. They not only provided wonderful service, but they were clearly motivated and dedicated to their profession, which made us feel that we were always in good hands. Ivan, as captain, made it clear that safety at all times was a top priority, and he worked with us ever day to make sure we had a good route and adventure plan. Marisia made three terrific and interesting meals every day, PLUS she had a snack laid out for us in the afternoons. Both of them made sure that we had everything we needed or wanted at all times. Put simply, we could not imagine having a better crew. The boat itself was fantastic; large cabins and comfortable bath/shower; plenty of room inside and out; fun to sail/motor, and nice features for swimming and getting on and off.

Steve D, aboard Catamaran Karma, April 2025  sailing the British Virgin Islands

Catamaran Sandy Cinco
Catamaran Sandy Cinco

Mike and Lizzy were welcoming and knowledgeable about the islands and history.  They made it clear up front if we needed anything or had questions to just ask.  Lizzy was an amazing chef!  She made sure that individual dietary needs were addressed and carefully distributed the dishes so everyone got what they requested. We didn’t have any real plans which put extra burden on Mike. He had a clear plan each day and it worked for us!

The yacht exceeded our expectations. The additional covered space on the top deck was great!  It allowed everyone to spread out and added a lot of space to relax. 

We were very happy working with Sailing Directions. Communication with us and the crew was excellent.

Jeff M, aboard Catamaran Sandy Cinco, March 2025  sailing the British Virgin Islands

Catamaran Ripple
Catamaran Ripple

This family vacation exceeded our expectations and made wonderful lifelong memories. Even after arriving home the crew of Ripple reached out to us sending additional photos and trip highlight video. Sailing Directions provided excellent service and prompt response to any questions we had.

Pete N, aboard Catamaran Ripple, January 2025  sailing the 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.