Crewed Caribbean Yacht Charters

Search for available crewed 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:

Fall 2014 and Spring 2015 Discount
Save up to $3,500 on 7 night charters occurring between 15th November and 15th December 2014, 1st and 31st January 2015 and 1st and 31st May 2015 sailing the British Virgin Islands aboard luxury crewed catamaran Soon Come.

Available for charters starting 15 November 2014 through 31 January 2015
Reservations need to be confirmed before 15 January 2015

5% Discount for 2014 and 2015
5% Discount is available for charters booked before 31 October 2014. The reservation may be for any dates outside of holiday weeks. Sailing the Virgin Islands from St Thomas.

Available for charters starting now through 30 July 2015
Reservations need to be confirmed before 31 October 2014

10 nights for the price of 7 in the Grenadines
Ten nights for the price of seven for Grenadines-based charters occurring between 1 August and 20 October 2014.

Available for charters starting 1 August 2014 through 20 October 2014
Reservations need to be confirmed before 1 October 2014

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 Flow

, British Virgin Islands crewed Catamaran charter, June 2014

"Roland and Vanessa were perfect; they could not have been more friendly, more attentive or more accommodating. We would definitely want to charter with them again. The food was amazing, delicious and beautifully presented. Everyone is talking about 'doing it again'."

Cindy P, sailing the British Virgin Islands


Catamaran Avalon

, British Virgin Islands crewed Catamaran charter, June 2014

"We're in-flight on our way home wishing we were still on the Avalon. We had such an incredible time! Alex, Carla and Molly were the best hosts ever and the Avalon was luxurious. We never saw a better craft on the water. Thanks for getting us on that boat!"

Larry G, sailing the British Virgin Islands


Catamaran Azuria

, US Virgin Islands crewed Catamaran charter, June 2014

"We had a fabulous trip, wonderful crew in Stewart and Donne' and have only the highest regard for our entire experience. Thanks again."

Sam H, sailing the US Virgin Islands

> See all of our crewed yacht charter Reviews!

Yacht Charter Virgin Islands Leeward Islands Grenadines Ask Us - Caribbean Charters
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.

Find your perfect crewed yacht charter vacation