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.

Lady J is offering a special lower rate of $95,000 plus expenses per week for charters in the Virgin Islands or Leeward Islands sailing 19 January - 19 February 2020.
Offer Dates:
19 Jan 2020 - 19 Feb 2020
Confirm before 3 Jan 2020 Expires in 18 Days
Save 20% off new reservations of 6 nights or longer for available dates through the end of January 2020.
Can not be combined with other discounts.
Offer Dates:
Now - 31 Jan 2020
Confirm before 10 Jan 2020 Expires in 25 Days
Save 20% off new reservations of 6 nights or longer for available dates through the end of January 2020.
Can not be combined with other discounts.
Offer Dates:
Now - 31 Jan 2020
Confirm before 10 Jan 2020 Expires in 25 Days

We had a great time on the trip. Fabi and Nim were fantastic in every way. We truly have memories from this trip that will last a lifetime. Thanks for all of your help in setting this up.

Mike F, aboard Catamaran Luna, December 2019  sailing the British Virgin Islands

This trip exceeded all expectations!

Ryan and Lesli were wonderful. Their personalities blended perfectly with our family. They were so attentive to anything we wanted at any time, even anticipating our needs before we asked. As a team, they couldn’t have been any more perfect.

Ryan is a great captain and unbelievably knowledgeable about many things beyond crewing that big yacht. Lesli is a superbly talented chef who served us three gourmet meals each day and made sure to accommodate any special request we had. The presentation was always lovely.

The yacht was spotless, looking brand new in and out. It was very comfortable and air conditioned to the perfect chill. We couldn’t have asked for anything more. The air conditioning was special but other aspects like the flying bridge seating, large comfy front mat, spacious cockpit, spacious salon, large staterooms, great showers, large storage areas, and the special water toys were all impressive. My son and his wife loved the coffee maker. The Seajet was a crowd favorite.

Ryan and Lesli had prepared an itinerary that was exactly as we had requested. We went to all of the spots that we had sailed years ago with our own boat.

As for your service, it was always on time and responsive to any question I had. Your website made it very easy to find specific information on any subject. Thanks for everything.

Susan R, aboard Catamaran Anastasia, November 2019  sailing the Virgin Islands

The crew was fantastic! Ian, the captain, put together a great itinerary that came together perfectly. Blair, the chef, did a phenomenal job with the meals. They truly looked and tasted like they came out of a Five Star restaurant. In addition, she was engaging and a joy to be around. Ian, the first mate, was a fantastic bartender and was always at the ready with a great story. You can always find a nice boat, but the crew made the trip.

The yacht was perfect. Not only was it spotless when we arrived, the crew kept it that way throughout the week. Everyone was very pleased with the size of the staterooms and the separate A/C controls in each stateroom.

The food was terrific, both in presentation and taste. Blair took our preferences and created unique, interesting and delicious meals each day. Ian put together a great itinerary with a different island each day

Sailing Directions made it very easy. They were very responsive when questions arose prior to the trip. The website was very informative.

Thanks for your help. It was a great trip.

Mike M, aboard Catamaran Mahasattva, November 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.