Book an unforgettable crewed yacht charter vacation.

View Available Yachts:

Book with the Caribbean specialists. For over 19 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 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 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.

Charter must take place by early August. 5-night minimum stay. Discount cannot be combined with any other offers.
Offer Dates:
Now - 1 Aug 2024
Confirm before 31 Jul 2024 Expires in 8 Days
Charter must take place by early August. 5-night minimum stay. Discount cannot be combined with any other offers.
Offer Dates:
Now - 1 Aug 2024
Confirm before 31 Jul 2024 Expires in 8 Days
20% off all charters run through July 2024. 6 night minimum stay, BVI ports required.
Offer Dates:
Now - 31 Jul 2024
Confirm before 31 Jul 2024 Expires in 8 Days
We could not have had a better week aboard the Salty Dog! We made memories that will last a lifetime. Gordon and Jenine made our family, spanning ages 6-64 feel extremely comfortable and pampered all week. The food was amazing, the service was amazing, the boat was amazing, the sights/excursions were amazing, and the company we shared was amazing. Gordon and Jenine quickly became extended family members which made saying goodbye more difficult. If you are on the fence about booking this trip, don't be! You will not regret it!

Stephen M, aboard Catamaran Salty Dog, February 2024  sailing the Virgin Islands

The crew was fantastic. Solid 10/10. They were knowledgeable, friendly, hilarious, and attentive to anything we needed or requested. Not only were they expert sailors and chefs, but they were so much fun to hang out with. The Yacht itself was incredible. It was meticulously maintained, modern, and equipped with so many fun toys. Our favorite part of the yacht (although hard to choose!) were the water toys and the sleeping accommodations. The itinerary was perfect. The crew set up a wonderful adventure for us and we got to see everything we wanted. The food was Michelin Star worthy, and we cannot say enough good things about Chef Richard's recipes and presentation. He was also a blast to hang out with (as were they all!)

Max M, aboard Catamaran Moon Shadow, February 2024  sailing the British Virgin Islands

This trip was amazing! In spite of less than ideal weather (high winds and big swells) Captain Doug made it possible to experience all but Anegada which would have been a long rough sail. Doug always had a plan and discussed it with us each morning for our approval…Gambit itself. Meticulously maintained, beautifully decorated and homey. Comfortable berths. Always a convenient place to put things which is important on a boat! … Our meals were also amazing! So tasty and beautifully presented by Val.

Mackie M, aboard Catamaran Gambit, January 2024  sailing the British 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.