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 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.

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

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 Sea Dragon, December 2022  sailing the Caribbean Leeward Islands

We are among one of the five couples that were recently in the BVIs on a sailing adventure aboard the Blue Pepper. You must know that The Blue Pepper experience, in EVERY way, was impeccable! The crew of Taylor, Denise and Liz were top notch. Together, they created a magical experience for us all. They worked tirelessly to make our sailing adventure relaxing and no detail was overlooked.

The boat was immaculately clean and beautiful! Denise’s absolute gift for preparing and serving delicious food was truly spectacular. We were blown away by her creativity and culinary skill. The crew were engaging, caring and their respect for the boat and their craft was most commendable.

I will most certainly recommend the Blue Pepper to our friends who are looking for an outstanding sailing adventure.


I just wanted to let you know how very impressed we were with Captain Taylor, Chef Denise and Liz. They absolutely MADE the trip for us.

The boat was immaculate and the attention to detail throughout the trip was amazing.

Denise's meals were spectacular - they were fresh, healthy and delicious - and the presentation was beautiful.

We felt like every meal came from a top tier restaurant - which was not something we expected.

Captain Taylor's easy-going Texas style made it seem like nothing was a problem - he put us at ease the entire trip - while we know he was in constant motion making sure that everything was perfect. And we LOVED Denise - so fun and personable! Liz was always there to make sure everything was presented just so.

The crew was fun - but also extremely professional and thorough. The Blue Pepper hosted 10 of us for a week - and it always looked like we had just stepped on board. I don't know how they did it. They set the bar for hospitality and service for any future vacations for us.

Larry N, aboard Catamaran Blue Pepper, January 2020  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.