Crewed Caribbean Yacht Charters
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 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
Expires in 38 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.

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Latest crewed yacht charter Reviews

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Amazing! Far exceeded expectations! The boat was awesome! Well kept.

The vacation was PERFECT. Matt and Hillary are the perfect couple. We called them Ken and Barbie. Never been treated better!!! Chef Rich was incredible also. Best food in our lives. Really! We all agreed that Rich was the best chef ever!

Daniel F, aboard Catamaran Lady Katlo, May 2016 sailing the US Virgin Islands

Everything about our week was beyond all expectations!

As a group we were beyond happy with the crew. What a team! Great at what they do. Fun loving, friendly, went above and beyond to make our trip all it could be and more. Nathan's dry humor was so enjoyable. Great job of daily cleaning and temperature control. Upper deck was wonderful. Water toys great.

Penny is a tremendous cook and did a great job with our preferences. Rave reviews for quality, imagination and presentation. It's obvious she loves cooking.

Nathan was very accomplished in showing us areas we wanted to visit.

Two hundred per cent better than our previous mono hull sailing charter!

Mat S, aboard Catamaran Amara, May 2016 sailing the British Virgin Islands

The crew was fantastic. Brendan was very professional yet fun to be with. The food Anastasia served was first class, and she was perfect as first mate.

Robert G, aboard Catamaran Pisces, May 2016 sailing the US 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.