Book an unforgettable crewed yacht charter vacation.

View Available Yachts:

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.

Any new charters booked before 31 December 2019 and completed by 1 June 2020 receive $1,000 off listed rate.

Valid on charters 7 nights or longer. Not available for Christmas/New Years weeks.

Offer Dates:
18 Nov 2019 - 1 Jun 2020
Confirm before 31 Dec 2019
Save 10% off the charter rate for new reservations sailing from Red Hook, St Thomas within 3 - 19 December 2019. 6 night minimum charter.
Offer Dates:
3 Dec 2019 - 19 Dec 2019
Confirm before 29 Nov 2019 Expires in 38 Days
Book a 7 night charter for the price of 6 nights aboard Zingara, the Matrix 76 catamaran, for up to 10 guests! Valid for new reservations occurring between now and 15 December 2019
Offer Dates:
Now - 15 Dec 2019
Confirm before 1 Dec 2019 Expires in 40 Days

We had an amazing vacation. Ryan was a very competent captain, he was knowledgeable and attentive, and at the same time knew when to be respectful of our family alone time. The boat was clean and well ventilated.

Ryan had recruited a young lady called Erin to fill in while Katie was away. Erin was full of energy, her cooking was amazing and it was definitely one of the highlights of our vacation (that young lady worked so hard!).

Ryan and Erin took Nick and Stephanie on some great dives. Another highlight of the vacation. They were very careful to make sure my 16 year old daughter was taken care of and safety always came first.

We were taken to all the locations that we had requested, and some that we hadn't, all great choices.

As parents of teens it is challenging to find a vacation that suits everyone, but this hit the mark, and we will have treasured memories to hold on to. We were also sad to say goodbye to Ryan and Erin, truly nice people!

We would have no hesitation in recommending Ryan - Erin will probably be chasing her dream somewhere else by the time we sail again!

Thank you again for all your help organizing. We will use you again for any future trips!

Nick E, aboard Catamaran Siren Song, July 2019  sailing the Virgin Islands

Adam and Emily were excellent! They were perfect for our group. Emily was fantastic chef. Food was excellent. Great itinerary. Excellent all around.

Bailey T, aboard Catamaran Stand By One, July 2019  sailing the Virgin Islands

I wanted to reach out to let you know what an what an amazing time we had on our recent sailing trip with Taylor and Margaret on Better Days. I can’t say enough great things about them. We would absolutely book another charter with them.

Taylor and Margaret are an amazing team and work seamlessly together-without their chemistry the trip wouldn't have been the same. Taylor's knowledge of sailing and the islands is remarkable-we learned lots of tidbits and history about the area. Taylor takes great pride in keeping the boat clean and making sure his guests are cared for.

Margaret's love for cooking showed in every meal she prepared-the food was beyond our expectations, absolutely delicious! She took special care in preparing meals, noting the likes and dislikes of our group.

It's been over a month since our trip, and we are still talking about how unbelievable it was. We can't wait to go back but understand they will be on a different yacht next year; we would most definitely book again for the crew-not the boat!

It's amazing how connected all six members of our charters felt connected with Taylor and Margaret after spending just a week together. We just LOVE Taylor and Margaret, they have a special place in our hearts now!

Stacy C, aboard Catamaran Better Days, July 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.