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

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 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 20% off all summer bookings aboard Luna sailing the Virgin Islands and Grenadines. Four night minimum charter.
Offer Dates:
Now - 31 Aug 2019
Confirm before 16 Aug 2019 Expires in 27 Days
Save $1,000 off weekly rate for up to 4 passengers, or $1,500 off weekly rate for 5 to 8 passengers sailing summer and fall 2019.
Offer Dates:
Now - 20 Nov 2019
Confirm before 31 Oct 2019
Save 15% off new reservations sailing now through 15 November 2019. Applies to new reservations 6 nights or longer.
Offer Dates:
Now - 15 Nov 2019
Confirm before 18 Oct 2019

I just wanted to drop you a note to thank you for your help booking our trip. Ryan and Leslie are great! They catered to what we wanted to do. I could go on and on. Anastasia is better than ever.

Priscilla F, aboard Catamaran Anastasia, July 2019  sailing the Virgin Islands

Nim and Fabiola were a joy and perfect for our family. Nim answered all of our million questions about boat and the sea while making sure everyone was safe. Fabiola was warm and accommodating every minute of the day.

Luna was immaculate. Nim ran the a/c for us in the afternoons and evenings making for a very comfortable stay. Loved the water maker, loved the coffee machine, and the kids loved the bean bags on the trampolines.

The food was fantastic and beautifully prepared. Fabiola took all of our preferences into account and nailed our favorites. Very impressive what she is able to prepare on a boat.

I believe I requested a fairly ambitious itinerary and we covered it all. One of our favorite spots was stopping in St John our first night. The anchorage was great and the snorkeling at Watermelon cay was spectacular.

Shaun F, aboard Catamaran Luna, July 2019  sailing the Virgin Islands

Captain Brian was unbelievable. His knowledge of the area and boat made the experience tremendous. He interacted greatly with the family (especially the kids).

Chef Hannah was a stand in for Alex and she prepared amazing meals and was a great hostess. Food was unbelievable and always within the preference sheet.

Our only wish was that the charter was longer to be able to go to Anegada.

Au Soleil was A+. Our favorite spot was the front layout areas and the fly bridge.

John H, aboard Catamaran Au Soleil, June 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.