Book an unforgettable crewed yacht charter vacation.

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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 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 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
Santa Ana is offering 20% off new reservations for available dates sailing in June or July 2019 sailing the Virgin Islands. 5 night minimum, discount may not be combined with any other special.
Offer Dates:
Now - 19 Jul 2019
Confirm before 3 Jul 2019 Expires in 15 Days
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

We had such a wonderful time and talk about it every day. A week packed with so many family memories. We loved the Kelea and we especially LOVED Alli and Dan.

Alli and Dan were THE best. So warm and personable, it was hard to say good-bye at the end of the week. They were always asking how we were doing and so accommodating with a variety of different requests, we kept them VERY busy!

Aboard Kelea we never felt like we were on top of each other. There were places all 8 of us could sit and visit, the trampoline, pads on top and of course the dinner tables. But we could also go off and find quiet spots to read, pray and enjoy the beauty of the scenery if we wanted to.

The food was AMAZING! Alli blew us all away with how delicious her food was, the variety was perfect and the presentation so pretty that I and my son-in-law took pictures of all the meals!

Every spot we anchored has its own unique characteristic. Dan did a great job bringing us to beautiful diving spots. Rhett and I dove 2 days and the rest of our 4 boys and son-in-law dove all 5 days. It was a great mix of diving locations, the Baths to explore, calm bays to pull the water toys behind the dingy and fun beach bar stops.

It was a trip of a lifetime. What I loved about this sailing trip at this stage of our life is that it was SO RELAXING! We are spread throughout the country now so I loved being together everyday, all day, doing so many memorable things, sitting and gazing at the scenery during a sail, visiting, playing games, eating delicious food that I didn't have to shop for, cook or clean up after, water fun, island fun etc.

Rhett H, aboard Catamaran Kelea, June 2019  sailing the British Virgin Islands

We loved both Jeff and Caitlin, lovely couple, fun and very respectful. Jeff is very experienced and knowledgeable. Caitlin is an amazing chef, always smiling and an incredible person.

The boat was beautiful, very comfortable, very clean. Both Jeff and Caitlin kept things impeccably clean.

What can we say about the food. WOW. We are Italian and food is very important to us. Caitlin is an incredible chef. The presentation, the taste, different variety each day, absolutely delicious. And she makes everything from scratch!

We loved all the islands we went to, the water, snorkeling, kayaking, just wonderful.

It was an incredible vacation. Our week on the boat with Jeff and Caitlin is unforgettable. We thank them so much for great memories on the boat.

Lorenzo S, aboard Catamaran Port to Vino, May 2019  sailing the Virgin Islands

We had a great week on Floatation Therapy! Andrew and Michaela are fantastic. Thanks for your help with this charter.

Andrew and Michaela were professional at all times, yet very engaging and fun. Michaela took the time to engage the young ladies on our trip and they really enjoyed interacting with her. Every meal was tasty and well presented. The food service was excellent and attentive.

Tarek B, aboard Catamaran Floatation Therapy, May 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.