Crewed Caribbean Yacht Charters

Availability Search

It is time to experience the vacation of a lifetime aboard a luxury, all-inclusive, professionally crewed catamaran, sailing or power charter yacht in the Caribbean.

Escape from the icy winter to white sandy beaches, consistently light Caribbean trade winds, clear blue water, gourmet dining and fresh cocktails, islands close enough for day sailing, outstanding game fishing, world-class dive sites, award winning yachts and crew, and sunshine every day of the year.

Sailing Directions® helps you find and reserve a crewed yacht charter in the Caribbean Virgin Islands, Leeward Islands and Grenadines. We can find you a charter yacht that best fits your budget and needs; from an all inclusive family sailing vacation to a corporate group or an unforgettable honeymoon. We provide a wealth of information and support throughout!

When you book a private crewed yacht through us you get all of our services as well as peace of mind that our advice is unbiased and your payments are held in a secure 3rd-party escrow account until the charter date.

Sailing Directions® is an independent crewed yacht charter brokerage with an extensive range of crewed yachts and a depth of expertise. We specialize in crewed catamaran charter vacations sailing the Virgin Islands. Let the experts match you with the perfect crew and yacht for your needs. We know all of the boats and have extensive knowledge of the local cruising areas. Start your search now using our live online availability search form or contact us now for your unforgettable Caribbean crewed yacht charter vacation!

Specials and last minute Discounts:

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Details:
Save $2,000 on 7 night charters in November and December 2016 (excluding Thanksgiving week) sailing the Caribbean Virgin Islands from St Thomas or Tortola.
Dates:
Available for charters starting 29 November 2016 through 17 December 2016
Reservations need to be confirmed before 6 November 2016
Details:
Sail the Caribbean Grenadines this summer with a 15% discount during July - October 2016. Charter one way from St Vincent south through the island chain ending in Grenada or return to St Vincent.
Dates:
Available for charters starting now through 29 October 2016
Reservations need to be confirmed before 1 October 2016

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!

Latest crewed yacht charter Reviews

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Yes Dear was extremely well maintained and the cabins far more spacious than I had anticipated. Our family enjoyed most of our time on the yacht either sunning on foredeck or relaxing in the shade at the stern.

The crew were hospitable, welcoming, friendly and professional. Hanrie’s mastery in the galley was amazing. Each meal (and hors d’oeuvre) was a creation.Christiaan was flexible and attentive to our preferences.

Sailing Directions was very accommodating, particularly in light of the various modifications we needed to make to our itinerary and dealing professionally and courteously with a last minute cancellation. I would recommend Sailing Directions and Yes Dear without reservations

Bruce P, aboard Catamaran Yes Dear, July 2016 sailing the British Virgin Islands

The most wonderful, inspiring and peaceful vacation. Thanks for the amazing hospitality and kindness of Amber & Diego - they're like family. Food = Fabulous. Fun = Diego taking the kids knee boarding and exploring the deep blue.

The knowledge they both have of the local customs, culture and wild life only enhanced out love of this trip. Thank you for spoiling us!

Kirk S, aboard Catamaran Dianna Rose, July 2016 sailing the Virgin Islands

Jenny and Jaco were the best crew that we've ever had. They were beyond accommodating, paying close attention to everyone's preferences regarding everything from the day's planned activities to each meal's preparation. Without gushing, I'll just say that they exceeded our expectations in every way.

A2 was very clean and nothing was ever out of place. My favorite aspect was the fly bridge, it had shade for those of us people with fair skin and an ample seating area for us all to be together.

Jenny food was beautifully presented and delicious. She paid close attention to everyone's food preferences, sometimes serving three different entrees to accommodate everyone. She did it graciously, never acting like it was an inconvenience to her. She prepared every dish perfectly, especially the duck. It was perfectly seasoned and cooked. She even surprised us with flavor combinations that we had never had before, which is hard to do considering that we own a restaurant. Her food was better than anything that we could get in any restaurant in the BVIs.

They made sure that everyone's wants and needs were met. Some of us wanted to swim, others wanted to snorkel, others wanted to do water sports, and others wanted to get off the boat and visit bars or play bocce. They made sure that everyone was happy and got to do the activities that they wanted.

Jenny is the best chef we've had on 8 charter cat trips. Jaco and Jenny would definitely be our preference for crew on future charters.

Bill G, aboard Catamaran A2, June 2016 sailing the British Virgin Islands

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Crewed yacht charter vacations in the Caribbean

Yacht Charter Virgin Islands Leeward Islands Grenadines Ask Us - Caribbean Charters
Charter the Caribbean

A crewed Caribbean yacht charter offers you freedom to explore paradise at your own pace, choose your itinerary, activities and have a personalized menu unlike any cruise ship, resort or beach side hotel.

With accommodation, a professional captain and a personal chef with all meals, cocktails, wine, beer, snacks, fuel, equipment and water toys included few other vacations offer such an unforgettable experience and value for money.

We offer a large selection of Caribbean charter yacht rentals including a fleet of luxury crewed catamarans based from St Thomas & Tortola, as well as full range of crewed power yachts, monohulls and catamarans based throughout the Caribbean to suit every budget.

Unlimited options include sailing the many and varied US and British Virgin Islands, sailing and diving in the undeveloped Grenadines or chartering a luxury power yacht in Antigua, St Martin & fabulous St Barts. See more information about the team at Sailing Directions.