Crewed Caribbean Yacht Charters

Start Here: Search for available Crewed Charter Yachts

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 and sunshine every day of the year.

Sailing Directions® helps you find and reserve a crewed yacht charter in the Caribbean. 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 yacht charter broker with an extensive range of crewed yachts and a depth of expertise. 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:

10% Discount for charters confirmed by 15 March 2015
Save 10% on Something Wonderful's rates in 2015 for reservations confirmed by 15 March 2015 sailing the British Virgin Islands.

Available for charters starting now through 16 December 2015
Reservations need to be confirmed before 15 March 2015

15% discount for charters in 2015
15% discount off Zuma's rates for charters booked for 2015 sailing dates (excluding Xmas and New Years weeks) sailing the Virgin Islands or Caribbean Leeward Islands.

Available for charters starting now through 17 December 2015
Reservations need to be confirmed before 15 February 2015

10% discount available
Save 10% off Flying Ginny's regular rates for any reservations booked between now and 31 January 2015 for charters sailing by the end of 2015 (Christmas and New Years weeks excluded)

Available for charters starting now through 15 December 2015
Reservations need to be confirmed before 31 January 2015

These crewed catamaran specials are available for new charters sailing from Tortola or St Thomas in the Virgin Islands. 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


Catamaran Best Revenge 5

, British Virgin Islands crewed Catamaran charter, January 2015

"We cannot say enough exceptional things about Nick & Lucy. From the first greeting they were extremely professional, but also very welcoming and fun to be around. They both were quick to figure out our needs, and were incredibly attentive & accommodating. The level of service was beyond anything we had ever experienced. They took great pride in making sure we were having a great time and we, quite honestly, loved being around them. While always making sure to tend to our needs, they also gave us personal space & according to our entire family, they are truly the reason why our trip was so memorable. Without a doubt, we ever do this again, it will be with Nick & Lucy. An amazing team! Five star crew!!

Being boaters ourselves, we can attest to the fact that Best Revenge 5 is a beautiful catamaran in every way! It was incredibly clean, well ventilated and extremely comfortable. The cabins were very well appointed and beautifully done. Beds are comfy (and are sized as stated!), plenty of storage and hanging space and bathrooms spacious (by boat standards) and well-appointed with all the necessities of the trip. The common areas are very well designed and spacious. Little extras all around the boat that made it comfortable for a group - we didn't feel like we were sitting on top of each other.

On top of being well designed and spacious, she was beautifully decorated! A true WOW! Our family felt incredibly lucky to be able to enjoy such a beautiful yacht. Again 5 stars to an amazing catamaran!

WOW!! There are not enough adjectives to describe the high level & exceptional quality of the food served. It was a culinary feast each & every meal! (Including the snacks!). Incredibly well prepared, well-balanced meals and catered to our individual food preferences. The presentation was top-notch and their attentive service during our meal was more than you could ask for. Little things like different table decor each meal, nice dinnerware just added to the ambiance. It was consistently spectacular every meal - we were all trying to figure out our favorite but they all ended up being our favorite! :-) Lucy is a Five Star chef!

We can't forget about the drink selections either. Nick was great at pairing wine selections for our meals. We got to enjoy his native South African wines which we really enjoyed as we had traveled there - such a personal touch. His skills making specialty drinks was second to none as well.. a real treat! Our entire family looked forward to his drink of the day, always fun, always tasty!

Our itinerary fit our family perfectly! It was adventurous, unique, and most importantly, fun! We were treated to some amazing land treks, sea adventures and incredibly beautiful spots. We could not have asked for more - we were all extremely happy with our adventure!

John, you were great to work with! It was first-class service in every respect. Prompt answers to questions, helpful insight in selecting the proper catamaran and crew for our trip, and pre and post follow ups. We would highly recommend Sailing Directions and if our future needs take us back to another sailing adventure, you will be our first contact!

BR5 & our crew were exceptional! First class, five star all the way! We can tell you without a doubt, that this surpassed our high expectations. Our crew was very proud to be on the BR5 and it showed in every aspect of our trip - from their professionalism, to accommodating our family in every possible way. She's a well appointed fun catamaran - lots of good toys to play with on board as well, which was a perfect fit for our active family! "

Lori H, sailing the British Virgin Islands


Catamaran Azuria

, US Virgin Islands crewed Catamaran charter, January 2015

"Donne cleaned the cabins, bathrooms and refused to let us make our own beds. Every morning as we sat for breakfast she hurried off to each cabin to clean as if we were just walking in for the first time.

The food was incredible. We told Donne and Stewart multiple times that we couldn't have gone to a restaurant and ordered that well three meals per day! The portions were perfect and she was even willing to share her recipes with us. The best part is we weren't rushed to sit for any meals yet when we were ready she reacted and served us immediately.

Our itinerary was great and only made better by Stewart and Donne's suggestions to us. Like something simple as a choice of a spa day at Peter Island or they could pack us champagne on ice and glasses in a backpack and they would show us a trail to hike to the top of Peter Island so we could see an incredible view of all the islands and toast a great trip!

John, you were so quick to respond to every question and I wouldn't hesitate to recommend you. In fact I've already sent your info to a friend. It couldn't have been easier and more efficient. "

Jimmy S, sailing the US Virgin Islands


Catamaran Gypsy Princess

, US Virgin Islands crewed Catamaran charter, January 2015

"The entire trip was a complete success. Shane and Anne were truly professional and made our vacation quite special."

Michael M, sailing the US Virgin Islands

> See all of our crewed yacht charter Reviews!

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Charter the Caribbean

Crewed yacht charter vacations in 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.

See crewed charter yachts available for your dates: