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:
Save 5% on Ma Ha's regular rates for charters sailing any time.
Dates:
Available for charters starting now through 30 July 2017
Reservations need to be confirmed before 30 April 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

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

Jeff & Caitlin were fantastic. Caitlin guided us on several snorkels. Great food. As good as the boat was, the crew was the boat’s best feature.

One person in our group can't have cheese so each meal they created special variation for her. Even baked cake the last morning so we could have "cake by the sea".

Really can't think of a single thing I would change with Sailing Directions’ service.

Don D, aboard Catamaran Happy Time, January 2017 sailing the British Virgin Islands

Sam & Rosemary did an amazing job and we were so happy that they were our Captain and Chef. Sam was so accommodating to our water activities especially taking our Daughter and Son-in-law scuba diving several times and at night. He took us to some of the best beaches and bars so now we have many fond memories to enjoy. He seems to be well respected by his peers and a very seasoned Captain. We have never seen two people work so hard, from morning to late night. If we ever do this again they would be our first choice for a crew.

Blue Moon is a beautiful boat, very clean, nicely decorated. We felt like we could have our own space at times to go read, relax and be alone or watch Sam sail the boat. As far as a best feature of the catamaran, we felt all the water activities that we were able to enjoy were amazing and the bedrooms were very comfortable. Slept like babies!

We can't say enough about Rosemary's menus and how she accommodated all our dietary needs from Vegans to meat lovers. Having to cook two different meals for every setting was telling of a wonderful cook. Her homemade cinnamon rolls were to die for and she even made them vegan so we all could enjoy them. So many delicious meals that we all gained some weight but it was well worth it. Like being at a 5 star restaurant! THANKS ROSEMARY!

John at Sailing Directions was always available to talk to and answered all our questions.

Sam and Rosemary were in constant contact with us before our sail to make sure they had all our requests and needs fulfilled. Thanks to Sam and Rosemary for taking us to the best spots in the BVI's!

Jane V, aboard Catamaran Blue Moon, January 2017 sailing the Virgin Islands

Our vacation was amazing. Jim and Amanda were so much fun. There aren't many people that can keep up with our family's sense of humor -but Jim - well he sure did! He felt like part of our family.

Amanda did an amazing job with the vast requests of foods-thanks! Catamaran vacations are definitely our family's favorite - I can't say enough about the experiences we had with Jim and Amanda!

Lisa M, aboard Catamaran Copper Penny, January 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.