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Experience the vacation of a lifetime aboard a luxury, all-inclusive, professionally crewed catamaran, sailing or power charter yacht in the Caribbean.

Escape to white sandy beaches, consistent Caribbean trade winds, clear blue water, customized gourmet dining and fresh cocktails, sheltered islands grouped close enough for great day sailing, world-class dive sites, award winning yachts and crew, and sunshine every day of the year.

Sailing Directions® helps you book a crewed yacht charter in the Caribbean Virgin Islands, Leeward Islands and Grenadines. We will match you with a charter yacht that best fits your budget and needs; from an all-inclusive family or couples sailing vacation to a corporate incentive party or an unforgettable honeymoon or anniversary charter. We make the booking process easy via our website and experienced charter brokers, provide a wealth of information and support to help you prepare for your trip and get the most out of your yachting vacation.

Sailing Directions is an independent crewed yacht charter brokerage which has been in business since 2005 with access to an extensive range of crewed yachts. When you book a private crewed yacht through us you get peace of mind that our advice is unbiased and your payments are held in a secure 3rd-party escrow account until the charter date. We also accept credit card payments through our secure website.

We specialize in crewed catamaran charter vacations sailing the Caribbean Virgin Islands. We have firsthand knowledge of the boats and crews and have broad knowledge of the Virgin Island cruising areas.

Find your ideal crewed yacht using our live online availability search form now or contact us to start planning your unforgettable Caribbean crewed yacht charter vacation!

Specials and last minute Discounts:

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Details:

The Annex is offering a free sleep aboard the night before your charter, to include boarding after 4pm, welcome cocktails and canapes, dinner ashore not included, boat provides breakfast the next morning.

Available for charters 6 nights or longer, excluding Christmas and New Years weeks.

Dates:
Available for charters starting now through 15 December 2018
Reservations need to be confirmed before 15 December 2018
Details:
Fly in the night before your charter and stay aboard Neverland for a free evening sleepaboard. Boarding after 5PM, includes welcome cocktails, then dinner to be taken ashore (dinner not included). Includes breakfast the next morning. Valid for 6 night charter or longer. Excludes Christmas and New Year weeks.
Dates:
Available for charters starting now through 15 December 2018
Reservations need to be confirmed before 16 November 2018
Details:

To celebrate their boat show success and kick start her first season in charter, Anastasia is offering 10% off new 2018 charter bookings of 7 or more nights, excluding holiday weeks.

Anastasia will be sailing the Virgin Islands and the Bahamas through April and will head down island to the Grenadines in May.

Dates:
Available for charters starting 7 January 2018 through 16 December 2018
Reservations need to be confirmed before 31 January 2018
Expires in 47 Days

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.

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Latest crewed yacht charter Reviews

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We had a fantastic time. It was a trip of a lifetime and we are well traveled.

The food was spectacular. Many meals were among the best we have ever enjoyed.

Our favorite aspect of the yacht was the upper deck.

We saw and did everything we had hoped.

Gene B, aboard Catamaran Tobarths, July 2017 sailing the Virgin Islands

Matt and Casey were wonderful. We couldn't have picked a better crew to be a part of our vacation. Our entire group would all agree that this was the best vacation we have ever had. I can't imagine going on another charter without Matt & Casey!

We enjoyed the Island R&R greatly. We found it clean, comfortable and well ventilated. The beds were very comfortable, and the a/c at night was wonderful. I am not sure if there was anything in particular that would be a favorite aspect as we were 110% satisfied the Island R&R. The accommodations were great, the water toys were great ( and the sling shot was really great ! ).

Casey did an outstanding job with our meals, everything was well presented and delicious. Casey took very good care of us for all the meals, snacks, appetizers and desserts. Not to mention the beautiful view you get to enjoy at every meal !

Our itinerary fit what we were looking for perfectly. We talked a bit about a few stops we wanted to make and left the rest to Matt. Matt did a great job guiding us to places that fit exactly what we were looking for. We were even fortunate enough to have some dolphins join us one day while we were in the water which was one of the high lights of the trip ! ( of which there were many )

Cant say enough how much we enjoyed spending time with Matt and Casey, I fact as we tell others about our trip, we all consider them part of the Family.

Kevin M, aboard Catamaran Island R&R, July 2017 sailing the Virgin Islands

Harvey and Marley were more than we could have asked for as a crew. The boat was very well maintained and very clean. The team provided outstanding hospitality that was second to none. They insured we had a safe and fun filled trip on the Ma Ha. We will be recommending this boat and crew to our friends and family. Truly outstanding! Rich and Sherry.

What a wonderful week! It exceeded our expectations by a mile. The beauty of the islands, beaches and coves are indescribable. Total relaxation in these very comfortable quarters with three other couples from Atlanta. All of this could not have been this is fantastic had it not been for our great hosts. Harvey - captaining the ship and making us feel at home and safe, Marley - her cooking and thoughtful menus and appetizers were perfect. This vacation we will never forget! Carlos and Deanna.

There are not adequate words to say how much we enjoyed our trip with you guys. You took spectacular views and wonderful friends and made them all the better! We have loved our time on the Ma Ha and we will be back! Kelly and Carlos.

We flew down from Atlanta with some very high expectations. Both of you exceeded them all. It was an amazing trip! Great itinerary! First-class service. We had everything we needed and more. Diane and I will recommend this to everyone. Tom and Diane.

Carlos C, aboard Catamaran Ma Ha, July 2017 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 and monohull sailboats 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.