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:

> See all Specials and Discounts

15% discount through November 2015
Save 15% on Lady Katlo's charter rate for any reservations taking place between now and 5 November 2015. Lady Katlo is available in the BVIs through late May and sailing in the Grenadines from mid June.

Available for charters starting now through 5 November 2015
Reservations need to be confirmed before 1 October 2015

10% Discount for Bahamas charters in August, September & October 2015
Save 10% on Something Wonderful's rates sailing the Bahamas this summer and early fall, August through October.

Available for charters starting 1 August 2015 through 30 October 2016
Reservations need to be confirmed before 19 September 2015

Save $500 through 27 July 2015
Save $500 on 7-night charters aboard the beautiful Lagoon 560 catamaran Blue Moon sailing the Virgin Islands through the end of July.

Available for charters starting now through 27 July 2015
Reservations need to be confirmed before 2 July 2015

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

"Our family thought everything about Gareth & Kristine was fantastic. They literally waited on us every hour we were awake. We felt guilty because of how hard they were working all the time. They absolutely understood our needs and concerns: From picky eaters with the kids to Mindi being concerned about rough seas. They continually optimized the itinerary to take into account potential weather and also learned more about our preferences as the first couple of days developed. We can’t imagine anything more they could have done.

Being aboard the Xenia, a Privilege 61.5 foot boat, was clearly a “top of the line” yacht! As we drove around other, similar sized boats during the week – we came to realize how “high end” the Privilege line is: More classic wood, less plastic, teak flooring on the outside vs just fiberglass, more high end electronics (Apple TV), TV’s in every state room, etc, etc. A very, very nice yacht!

Kristine was incredible! It was always a sit down, being served meal. From others that had chartered on other boats, I was expecting some food to be “set out, sorta buffet style”. The food was great each and every time. We commented a few times how we want her recipes and that she needs to publish a cook book! Everything seemed to be from scratch, example: she personally “glazed” pecans with her own candied mixture for a salad one day. The list is too numerous to mention.

It was just a wonderful experience and Gareth and Kristine were great! We can’t say enough good things. We definitely will call you if we consider chartering again. "

, aboard Catamaran Xenia, March 2015 sailing the British Virgin Islands

"The crew were amazing. Absolutely exceeded our expectations. We were a bit nervous about it as we had not done a charter before and since it was just the two of us it was important that we spent the week with nice people. They were super fun and friendly and certainly made us feel very comfortable. They accommodated our needs and were flexible to adjust things as the week went on. Can’t say enough good things about them. Learned a lot from Greg about sailing in blue water and we had a great, relaxing vacation.

The boat was immaculate and they keep it in incredible shape and very clean.

The food was fabulous – Vanessa is a very good cook and she was very creative. Great tastes, fresh food and beautifully presented. Very talented.

The BVIs is beautiful area we have not been before and will definitely go back. We will definitely be doing another trip in future – hopefully next year."

, aboard Sailing Yacht Blue Passion, March 2015 sailing the British Virgin Islands

"Everything was beyond exceptional. Food, itinerary, activities, boat etc. Graeme, Lauren and Zayne were unbelievable hosts. I would have no issue making a recommendation for either the crew or the boat."

, aboard Catamaran Something Wonderful, March 2015 sailing the British 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: