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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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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.

Available for charters starting now through 15 December 2018
Reservations need to be confirmed before 15 December 2018

5% discount available for new bookings 6 nights or longer taking place in 2018 excluding including Christmas and New Year weeks.

Lir is available in the Virgin Islands this winter, then Bahamas May through early June and then will work their way down the Leewards to the Grenadines for July and August 2018.

Available for charters starting now through 15 December 2018
Reservations need to be confirmed before 31 October 2018

Save $2,500 off new 7-night charters sailing the Virgin Islands through mid July and in the Grenadines through 12 August 2018.

Luar is also offering a free sleepaboard the night before your charter.

Available for charters starting now through 18 August 2018
Reservations need to be confirmed before 20 July 2018

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

> See all of our crewed yacht charter Reviews

Brand, Jayde and Louise were truly the perfect crew for our group. Their level of professional hospitality they provided was unbelievable. This trip exceeded our expectations.

Brand was able to navigate the USVI and BVI taking us to amazing areas based on the weather ( changing winds), our needs and activity desires. He quickly bonded with our 5 boys and was a constant source of entertainment: Scuba, wakeboard, subwing, tubing, fishing,and just doing flips off the boat with the kids. He makes some great drinks as well. Also full of worldly lnowl;edge and always a pleasure to talk with

Jayde- what an amazing chef! how she makes beyond restaurant quality meals in a 6 x 10 kitchen is unbelievable. She adapted to our groups needs and requests. She always had a smile on her face and was simply a pleasure to be around. She is the Seahome "glue" for sure

Louise- she took care of so many things behind the scenes they cant be counted. From keeping our rooms comfortable, to filling in gaps with the kids playing games, snorkeling, and packing snacks for a beach trip, etc AND we cant forget those unbelievable desserts and making sure drinks were always filled.

The crew worked so well together in perfect harmony. Our request list was 100% met, food was amazing, and we had fun from the moment we woke up to the moment we went to bed. Seahome was in immaculate condition and easily accommodated our group of 9. We never felt crowded.

John at Sailing Directions was always available to answer our questions and guided us through the charter process since this was our first time. Great customer service

Brian J, aboard Catamaran Seahome, March 2018 sailing the Virgin Islands

We were a group of three couples for 7 nights on the Island R and R Catamaran “Leopard 46” with crew Matt and Casey. They simply delighted us from start to finish with a well-rounded tour of so many delightful bays, beaches, bars and daily activities of hiking, snorkeling and site seeing. Their flexibility and range of options made for a truly wonderful trip. We were always in awe of what was offered in both the British and US Virgin Islands. The onboard hospitality, food and drink was truly 5 star.

Matt and Casey were in touch with us prior to arriving in St Thomas, very helpful with getting us from our hotel to the boat. Met us with open arms at the Dive Bar prior to boarding. A great option to “overnight” with Casey and Matt before we sailed. We all got to know each other, we got to settle in, and it allowed us to get a great early start on the first day. They had great and extensive knowledge of all the sites along the way. They were very helpful in giving us a range of options and choices for things to do, places to visit and sites to see. Extremely helpful and flexible in planning out each and every day.

Island R&R was clean and comfortable. The front bean bags were a great option. The dining area at the back was also one of our favourites for breakfast lunch and dinner. Of course we must give special mention to Darnell the Duck for floating on. Snorkeling equipment in great form. The floating “mat” was also a great place to lolly gag when tied up.

Oh my, the food! Casey and Matt did an extraordinary job. Case did handle the bulk of cuisine but Matt assisted on many occasions. Casey had us totally delighted and the dietary customization made our one “non seafood fan” very happy. Some terrific creations. We’ve asked for recipes.

The itinerary was awesome. It was really great to start off with a quick sail and then a snorkel for us all to get comfortable with the boat, as well as the crew. A special treat was Pizza Py in the first bay we visited before sailing on for a few hours that afternoon.

Great service from Sailing Directions - always straight forward - informative. The website is clean, informative, straight forward.

Ferg D, aboard Catamaran Island R&R, March 2018 sailing the Virgin Islands

Ryan and Jill were fantastic. Ryan is an excellent captain and Jill is equally good as a chef. They spoiled us. They are also very patient, answered all of our questions and were fun to hang out with.

We enjoyed the owners-version suite which was quite spacious. We really enjoyed sitting on the back part of the boat reading and watching the beautiful scenery as we sailed by.

The food was excellent. Jill’s presentations were beautiful. We experienced a new area to spend the night every day. They were all fun and scenic. Very happy with all aspects of the trip. We are certain that we will do this again one day.

Russ K, aboard Catamaran White House, March 2018 sailing the Virgin Islands

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Crewed yacht charter vacations in the Caribbean

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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.