Book an unforgettable crewed yacht charter vacation.

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Book with the Caribbean specialists. For over 18 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

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 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.

Catamaran Felix
Catamaran Felix

The crew was wonderful. Kayla and Chris fit in with our family perfectly and made us feel comfortable and at home aboard Felix. Their humor and knowledge were both greatly appreciated!

The food was fantastic; Chris truly spoiled us! I personally have a challenging diet with several allergies and he made sure every meal felt complete vs feeling like an “allergy friendly” meal. And it was all delicious!

The yacht was very comfortable and clean. It had all of the accommodations we needed - nothing was missing... I enjoyed the various different viewpoints to sit or lounge at while we went from island to island.

 

Kress S, aboard Catamaran Felix, November 2023  sailing the Virgin Islands

Catamaran Excess
Catamaran Excess
We had an absolutely PERFECT trip. We could not have imagined anything better. Captain Dan was amazing. He was professional, made us feel safe and suggested a great itinerary based on our requests. We did everything on our list and more. He made extra efforts to make sure we were having a great time and to get us to destinations so we could enjoy. He has a great personality and was very welcoming. He organized island transportation and provided a great experience at each location. We made a request to watch an NFL playoff game while on the boat. He went to every effort to make that happen. He made reservations for us at SABA rock bar to watch it there and was able to get the game projected on the boat so we could finish watching while eating dinner. Very impressed with him.

Chef Vanessa prepared delicious meals that exceeded our expectations. She catered to several dietary requests of our group and succeeded in making everything delicious. She had coffee waiting for us in the morning. She prepared healthy and delicious meals and included local fresh herbs, fruits and vegetables. She was very professional and readily available if we had any requests.

The yacht was in pristine condition. It was clean and well kept. The tender, paddle boards, and floating dock were also in pristine condition. Snorkel gear was able to be fitted to each person and was very clean. Towels and sunscreen were always readily available.

Melody D, aboard Catamaran Excess, January 2023  sailing the British Virgin Islands

Catamaran Cashmere
Catamaran Cashmere
Our trip was so perfect that we wanted to stay longer! ...I t was our 6th time doing this type of vacation onboard a sailing catamaran and it was the BEST! Of course, I would say that 80% of our trip is made of the chef and the captain … and they were just perfect. So professional, the quality of food, service and everything was overwhelming.
Julia, our chef, is sooo talented. The captain James and her read and followed every piece of our preference sheet and conversation with them...
The boat itself was in order, clean and we really liked the 2nd “deck” area where we could have a perfect 360’ view during nav...
They were able to fix a small electrical issue they had without us even realizing!

Mathieu C, aboard Catamaran Cashmere, December 2022  sailing the Caribbean Leeward Islands

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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.