Book an unforgettable crewed yacht charter vacation.

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Book with the Caribbean specialists. For over 13 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 $1,000 off new reservations aboard Oui Cherie with her talented crew. Discount can be prorated for 6 night charters.
Offer Dates:
Now - 17 Dec 2019
Confirm before 15 Nov 2019

Lower 7 night rates for new reservations this summer sailing the Caribbean Grenadines from Grenada:

2 guests: $28,500 7 nights
3 guests: $29,000 7 nights
4 guests: $29,500 7 nights
5 guests: $30,000 7 nights
6 guests: $30,500 7 nights
7 guests: $31,000 7 nights
8 guests: $31,500 7 nights

Offer Dates:
1 Jul 2019 - 31 Aug 2019
Confirm before 16 Aug 2019
Ring in the new year with 10% savings on your 6+ night charter sailing the Virgin Islands in January or February 2019.
Offer Dates:
Now - 28 Feb 2019
Confirm before 18 Feb 2019 Expires in 0 Days

Dylan and Isabella were amazing. Slivochka was very clean and comfortable. Our favorite spot was probably the fly deck. Amazing views and a wonderful opportunity to visit with Dylan and learn about the Islands.

I can’t even tell you how wonderful the food was. It was so good my children wanted to take Bella home with us. We are still talking about how good the food was.

The itinerary was great. The crew really accommodated our wishes for beaches with as few people as we could get. We had some amazing anchorages.

Katy S, aboard Catamaran Slivochka, February 2019  sailing the Virgin Islands

The crew, Taylor and Denise were friendly, knowledgeable, attentive and accommodating during the trip.

Yacht Blue Pepper was very comfortable, clean and well ventilated, I really liked layout of the cabins and their comfort.

Food was great! The chef customized the menu to our preferences 100%!

Everybody loved the itinerary of the area that we sailed.

Hope to be back next year and sail with the same great CREW aboard Blue Pepper.

Jack C, aboard Catamaran Blue Pepper, February 2019  sailing the British Virgin Islands

We departed our amazing charter today at noon. Port to Vino is a beautiful catamaran, well maintained and well equipped. The layout was perfect for our group of 4 couples. Could not have recommended a better fit for our group.

Jeff and Caitlin did a wonderful job managing our charter, cooking for us and entertaining us, kicking off each afternoon with Jeff specialty cocktails and finishing up with wines and desserts. They are an amazing team making the service for 8 individuals look easy and providing transitions flawlessly throughout our days. Both have so much to share of their marine knowledge and were so inclusive in helping us shape our charter route.

We had a stellar vacation week aboard Port to Vino. Thank you so much for your expertise in matching our needs and desires to such a beautiful boat and such an outstanding and accommodating crew. We would recommend your services, Caitlin and Jeff and Port to Vino with our highest regards.

Katrinia Y, aboard Catamaran Port to Vino, February 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.