Crewed Caribbean Yacht Charters
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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 Virgin Islands, Leeward Islands and Grenadines. 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:

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Details:
Save $4,000 on 7 night charters aboard Altesse for available dates through 31 July 2016 or $2,000 on 7 night charters in November and December 2016 (excluding Thanksgiving week) sailing the Caribbean Virgin Islands from St Thomas or Tortola.
Dates:
Available for charters starting now through 17 December 2016
Reservations need to be confirmed before 6 November 2016
Details:
Sail the Caribbean Grenadines this summer with a 15% discount during July - October 2016. Charter one way from St Vincent south through the island chain ending in Grenada or return to St Vincent.
Dates:
Available for charters starting 9 July 2016 through 29 October 2016
Reservations need to be confirmed before 1 October 2016
Details:
Save 10% on London Sky's charter rates for 5-night or longer charters sailing the Virgin Islands or Grenadines.
Dates:
Available for charters starting now through 7 August 2016
Reservations need to be confirmed before 9 July 2016

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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We all had amazing trip. Thanks again for all your help putting it together.

The crew was both great and very friendly and sailed us to all the great spots. I would easily recommend them for any charters. The food was incredible no complaints! We went to all the best spots. Peter Island Anedegan etc. This was my 3 time on a Privilege catamaran - they are the best.

Sailing Directions has been the best charter service I have used. Very fast responses. Thank you John for your superior customer service.

Bill T, aboard Catamaran Lady Dominique II, April 2016 sailing the British Virgin Islands

We cannot rave enough about how amazing our vacation was!

Tyler and Kelsey were amazing! They were incredibly knowledgeable about the islands and were always willing to teach us about where we were. Tyler was an amazing dive master and helped us complete our open water certification. We always felt 100% safe with him and he was very patient and professional.

Kelsey was an incredible tour guide especially at the Baths where she took us into nooks and crannies we never would have found on our own. She was also a great photographer and took so many amazing pictures of our group. They were always attentive to our needs and we never had a need or a want left unmet.

The boat was perfect. We had concerns that it would not be big enough for our group of 5 before we left however we couldn't have been more wrong. The cabins were totally adequate and the commons areas were plenty big enough. The air conditioning in the cabins are night worked wonderfully. Our favorite aspects of the boat were the fresh water spigot on the back of the boat, the bean bags and chairs on the front of the boat and the video screen to watch movies or play video games on at night.

The food was absolutely incredible. We had previously wanted to dine ashore one night but after eating the amazing food we changed our minds and decided we would rather eat on board. Every meal was impeccably presented and tasted like gourmet restaurant quality. Every dessert was better than the night before. The menu was customized to our preferences and everyone was beyond satisfied at every meal even though we have different dietary preferences. Our food and alcohol preferences were met to complete satisfaction.

We loved the itinerary we sailed. We told Tyler and Kelsey the first day the few places that were a must to visit and then we told them to take us to their favorite spots, we were not disappointed. They showed us so many beautiful places and took us to amazing diving and snorkeling spots.

Sailing directions was always fast to respond to emails and they helped to recommend this boat for our group and we were not disappointed. We would defiantly use Sailing Directions again, John did an amazing job for us this time and I'm sure he would again!

We cannot say enough about how much we enjoyed our vacation. Sailing in the Virgin Islands is such an incredible and amazingly beautiful experience, doing it on a catamaran with Tyler and Kelsey as the crew makes it a world class vacation. There is nothing better than rolling over in bed in the morning to look out your porthole at the gorgeous turquoise waters then going to eat a deliciously prepared breakfast and spend the day exploring the islands!

Meredith M, aboard Catamaran Two If By Sea, April 2016 sailing the US Virgin Islands

Nathan and Penny were perfect! We knew they would be great, but they exceeded our greatest expectations.

Amara was perfect! It is very spacious, with 3 completely different living areas: the bow, the fly bridge, and the stern. PLENTY of space to get away from the crowd if needed, but also plenty of space in each area for the whole group to hang out together

We are a five star meal three meals a day every day! The food definitely exceeded expectations. We had one gluten free, one dairy free, one both, and the other 5 with no specific dietary needs. And all 8 had one of the best meals we've ever had every single meal!

The itinerary was perfect (and seemed to be tailor made for us), and even when the weather or waves made Nathan change his plans the day was still perfect.

Sailing Directions did a great job of organizing our trip.

Everything was perfect! Definitely the best vacation ever!

Randy G, aboard Catamaran Amara, April 2016 sailing the British Virgin Islands

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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, 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.