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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
Save 10% off new 7-night reservations sailing in 2018. Special excludes Christmas and New Years dates.
Available for charters starting now through 15 December 2018
Reservations need to be confirmed before 1 November 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

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

> See all of our crewed yacht charter Reviews

Byron and Dianne were a delightful to spend a week with. Byron was very knowledgeable and glad to share his knowledge. I honestly don’t know what they could have done to make our trip any better.

The boat was kept very clean and they ran the air every night. It is a very solid boat.

The food was out of this world. My family did not even want to go to shore for dinner. Dianne is a very talented cook. Everything was fresh and healthy.

We enjoyed the Virgin Islands very much. There was just enough sailing and activities and the weather was perfect.

We found Sailing Directions’ very detailed website helpful in deciding which boat and where to go.

Ladson B, aboard Catamaran Sea Chateau, April 2018 sailing the Virgin Islands

Our time aboard Steppin Up with Bill and Michelle was perfect! We’ve sailed on crewed charter at least a dozen times, all over the Caribbean, and this was undoubtedly our best crew. They were welcoming, gracious, fun, funny, helpful, professional, everything you could ever ask for in a charter crew.

The food was delicious, the boat clean, well ventilated, temperature perfect, and in good working order.

We were concerned that we might notice a reduction in activity in the Virgin Islands due to hurricane damage however Bill and Michelle took us so many wonderful places that we never missed some of our old standbys. I would sail with them again, no question.

Sailing Directions, John, was also most helpful during the selection process. Thanks for all!

Kriss H, aboard Catamaran Steppin Up, April 2018 sailing the Virgin Islands

Tyler and Erika were both great. They both showed extensive knowledge and we were always sure we were safe and well cared for. Professionally, they were spot on.

But what really was terrific about both Tyler and Erika was how they personally invested themselves into sharing their local knowledge and other skills to help our family have the best trip possible. Whether it was the cooking, or the scuba training, or the ushering us around the great spots they suggested- they made sure we had a fantastic trip. Perfect.

The boat was great- very clean, and very comfortable. I loved sleeping outside under the stars (with my daughter) a couple nights, and the dinghy made getting out and about an easy experience.

The food was fantastic, it was expertly prepared and a lot of obvious thought put into matching our tastes.

We loved the (active) itinerary that we enjoyed, and the destinations were special and fun. Tyler and Erika obviously listened to what we thought made sense, and then made sure our stops fit in the most entertainment possible.

David Y, aboard Catamaran Free Ingwe, April 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.