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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:

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.

Dates:
Available for charters starting now through 15 December 2018
Reservations need to be confirmed before 31 October 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 now through 16 December 2018
Reservations need to be confirmed before 31 March 2018
Expires in 33 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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The crew was amazing. Very friendly, attentive and accommodating. Amanda too! By the end of the charter, we all considered them friends.

The Lir was comfortable, clean and well ventilated. We all slept very well! Favorite aspect? All the various places to sit and take in the amazing view. Also the fact that it was equipped with snorkel gear, a kayak, water skis, and stand up paddle boards. We used them all!

The food was amazing and we all appreciated that it was healthy too! Vanessa did a great job of taking 8 different likes and preferences and folding them all into a delicious meal.

Martha D, aboard Catamaran Lir, February 2018 sailing the Virgin Islands

We had a great trip. Jim and Amanda were fantastic! Jim did an excellent job getting us around the islands in a safe and comfortable manner. He was flexible about our weekly plans and sat with us every morning to plan the day. Amanda was pleasant, professional and amazingly efficient. Their knowledge of the islands was invaluable in helping us plan our week. Additionally, they were just fun to be around. We would sail with them again.

Copper Penny was an excellent craft that has been extremely well maintained and clean. The cabins were comfortable and spacious. Our favorite aspect of the yacht was the fly bridge. We spent a good bit of time up there having cocktails and enjoying the view.

The food was excellent. Well plated, good portions and very tasty. The chef followed what was on our preference sheet.

This is the second time I’ve used Sailing Directions and every aspect of the transaction has been very professional.

Tarek B, aboard Catamaran Copper Penny, February 2018 sailing the Virgin Islands

The trip was awesome. Thank you for suggesting a crew that was experienced and knowledgeable of the area as that was important to us. The captain and chef were accommodating to all our needs and wants.

This was my fourth trip to BVI aboard a chartered, crewed catamaran and I can, without hesitation say our chef, Risa was the best. Her presentation and quality of food was fabulous. Everyone agreed she was over the top. We all wanted to bring her home with us.

You did a great job of hooking us up with a great crew and outstanding boat, the Neverland experience was The Best!

Beverly L, aboard Catamaran Neverland, January 2018 sailing the Virgin Islands

> See all of our crewed yacht charter Reviews!

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.