Availability Search

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, award winning yachts and crew, 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 crewed yacht charter brokerage with an extensive range of crewed yachts and a depth of expertise. We specialize in crewed catamaran charter vacations sailing the Virgin Islands. 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
Details:
$1,000 per week discount for any new charter sailing in 2017. Discount does not include one appetizer and dinner (you'd dine ashore for this).
Dates:
Available for charters starting now through 17 December 2017
Reservations need to be confirmed before 1 November 2017
Details:

5% Earlybird discount off the listed rates for charters sailing between 1 December 2017 and 1 August 2018 - that 's right, a year from now - Book early and SAVE!

Does not include holiday weeks.

Dates:
Available for charters starting 1 December 2017 through 1 August 2018
Reservations need to be confirmed before 29 April 2017
Details:
15% off any charter taking place from now until 31 March 2017 sailing the Grenadines.
10% off any charter taking place in April 2017 sailing the Grenadines, Leeward Islands or Virgin Islands.
Valid on new bookings only. Inquire for less than 7 nights..
Dates:
Available for charters starting now through 30 April 2017
Reservations need to be confirmed before 1 April 2017
Expires in 32 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.

> See all of the current crewed yacht charter Specials and Discounts!

Bermuda 2017 America's Cup

Charter a Crewed Yacht at the Bermuda 2017 America's Cup

Latest crewed yacht charter Reviews

> See all of our crewed yacht charter Reviews

Our group of 8 had a wonderful time! Gareth showed us his sailing expertise, which everyone loved! The food, honestly was out of this world delish! We snorkeled, dove, shopped, hiked, paddle boarded, ate and drank our way through the BVI! Both Kristine and Gareth were always up for anything and always smiling! We kept referring to the BVI as a Disneyland for adults! The Xenia 74 is the most beautiful, well-kept catamaran!

The food was seriously amazing!! I can’t have gluten and one other guest couldn’t have sulfites and Kristine did a great job accommodating everyone.

Gretchen G, aboard Catamaran Xenia 74, February 2017 sailing the Virgin Islands

We had a wonderful trip. Joseph and Britta were awesome. They far exceeded our expectations. We could not ask for a better crew. The yacht was also great. Every detail was covered. Our favorite part of the yacht was the crew. Don’t get me wrong the yacht was great, but Britta and Joseph added such a personal touch for the whole event.

The food was spectacular. We ate every meal on board. We could not bring ourselves to eat anywhere except on board the Dianna Rose. We have been to the Virgin Islands several times and for the first time we actually had a culinary experience. The venues and voyage itself was also superior.

The crew was very accommodating with our desires. The whole experience was a 10 out 10. We would certainly recommend you, Sailing Directions, and the crew of the Dianna Rose. We will certainly utilize you in the future and recommend your organization.

Thanks so much for your assistance and making this trip a great success.

Shannon B, aboard Catamaran Dianna Rose, February 2017 sailing the Virgin Islands

Matt, Hillary & Richard exceeded our expectations and we couldn't have asked for a better crew.

Everything was lovely aboard the yacht and the water pressure in the showers was especially impressive compared to other boats we have been on.

The food was delicious. We asked the chef to make his favorite dishes and he did. The food was wonderful!

Will definitely contact Sailing Directions when we are ready to do another sailing trip and we have already recommended you to our friends.

Machie M, aboard Catamaran Lady Katlo, February 2017 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, 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.