Book an unforgettable yacht charter vacation.

View Available Yachts

Since 2005 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 with the crewed Caribbean yacht charter specialists.

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 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 $1,500 on the 7 night rate on charters through April 2019. Applies to the next 5 charters booked.
Offer Dates:
Now - 30 Apr 2019
Confirm before 9 Apr 2019
Enjoy 10% off the standard rates for 7+ night charters in January 2019. Gift yourself some time to relax with paddle board yoga, gourmet dining, and a spin on a sailing dinghy.
Offer Dates:
1 Jan 2019 - 31 Jan 2019
Confirm before 21 Jan 2019 Expires in 41 Days
Enjoy 10% off the standard rates for 7+ night charters in January 2019. Begin the new year with some play time in the Caribbean! Water toys, scuba diving, and a souvenir Klean Kanteen from your vacation.
Offer Dates:
1 Jan 2019 - 31 Jan 2019
Confirm before 21 Jan 2019 Expires in 41 Days

Tyler & Kelsey were awesome.

Re Playtime: We loved it all. Like the convenience of having an icemaker and water maker. We enjoyed the upper deck lounge area as well.

The food was wonderful, tasty, and customized to dietary preferences. It was always beautifully presented.

We enjoyed everywhere we went. Kelsey was like our personal tour guide offering stories, fun, historic & scientific facts.

Thank you!

Jamie H, aboard Catamaran Playtime, July 2018  sailing the Virgin Islands

We had a most wonderful vacation with Andrea and Morgan.

Captain Andrea revealed beautiful snorkeling locations to us and showed us the joys of sailing in the BVI.

Morgan was delightful. She provided lovely meals catering to everyone's tastes - sometimes cooking up to three varieties of a meal at a time. Not only was she a wonderful cook, but she was a great role model for the teenage girls on the trip - she was interesting, caring and accomplished.

Captain Andrea struck the perfect balance - engaging with us and giving us space all on the same trip. We can't wait to charter another trip. It's been a long time since we were so very relaxed. Our trip on Nemo accomplished maximum relaxation!

Thank you for everything. Please extend our tremendous thanks to Captain Andrea and Morgan. They provided us with amazing memories for our lifetime!

Karen N, aboard Catamaran Nemo, July 2018  sailing the Virgin Islands

Theunis & Rebecca were friendly, knowledgeable, attentive and accommodating. Great crew.

We love the king size beds aboard Anastasia. Theunis is a wealth of information. Rebecca is a great chef. Could not have had better food anywhere.

John at Sailing Directions was a great help in planning this trip. He always answered my emails in a timely and helpful manner.

Priscilla F, aboard Catamaran Anastasia, July 2018  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.