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.

Santa Ana is offering 20% off new reservations for available dates sailing in June or July 2019 sailing the Virgin Islands. 5 night minimum, discount may not be combined with any other special.
Offer Dates:
1 Jun 2019 - 19 Jul 2019
Confirm before 3 Jul 2019
Save 15% off new reservations sailing the Virgin Islands during May 2019
Offer Dates:
1 May 2019 - 31 May 2019
Confirm before 17 May 2019 Expires in 28 Days
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 20 Days

Our experience was fabulous. Tyler and Kelsey fulfilled all our expectations, they were friendly, accommodating, knowledgeable and most of all, created just the right atmosphere for a wonderful vacation.

Playtime was in tip top shape, clean and spacious, just the right size for three couples.

The food was great, thanks to Tyler and Kelsey exceptional culinary skills. Every meal was tasteful, beautifully presented, and just the right amount.

As far as the itinerary, we told Tyler and Kelsey what we were interested in (mostly snorkeling, diving, sailing and just relaxing) and they guided us to right spots.

As far as Sailing Directions, your website was very informative and you were very responsive whenever I called or emailed with questions. I will not hesitate to call on you in the future to book any future sailing trips. I will recommend you to friends who are interested in sailing. All of us felt that we will have to get back.

I want to thank for a trip of a lifetime and we are all looking forward to work together on future charters.

Isam Z, aboard Catamaran Playtime, April 2019  sailing the Virgin Islands

I wanted to thank you for playing your part and organizing our charter. It truly was a memorable experience. Probably one of the best vacations I have ever taken. Ryan and Leslie are superb. I cannot say enough about their hospitality, professionalism, ability to interact with both us and the kids. We are already looking at March of next year to book a second trip.

Frank V, aboard Catamaran Dolphin Daze, April 2019  sailing the Virgin Islands

John and Shirelle have a particularly good chemistry together, which was nice to be around. Shirelle is so positive and was always checking in on us for drinks, snacks, etc. John was highly competent, did excellent scuba instruction for our party, totally flexible if we wanted to stay longer at a destination, as well.

The food was enjoyable and well-presented and Shirelle customized it a lot to suit our tastes. She tended to go with shared salads of different types for lunch and plated dinners in the evening. The mix of lighter and heavier fare was good. The grilled meats were particularly good (steak, lamb) as was the inventive use of spices and ingredients to keep everything fresh and new!

Captain John customized an itinerary that worked very well for us based on feedback the first evening. We had the perfect mix of water sports, beach time, land time, cruising and sailing.

William W, aboard Catamaran Serenity Now, April 2019  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.