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 offshore 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 or couples group sailing vacation to a corporate party or an unforgettable honeymoon or anniversary charter. 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 and price point. 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:
$2,500 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 15 December 2017
Reservations need to be confirmed before 1 November 2017
Details:
Save 10% off any new 6 night or longer reservation sailing by the end of August 2017 and take a bonus free sleep aboard the night before. Sleep aboard includes boarding after 4pm, welcome cocktails and canapes aboard then dinner ashore (dinner not included). Also included is breakfast the next morning before setting sail.
Dates:
Available for charters starting now through 31 August 2017
Reservations need to be confirmed before 1 August 2017
Expires in 38 Days
Details:
Eclipse is offering 10% discount off the regular rates for new charter reservations taking place anywhere in the Caribbean from the Virgin Islands to Grenada now through 25 July 2017.
Dates:
Available for charters starting now through 25 July 2017
Reservations need to be confirmed before 1 July 2017
Expires in 7 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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The entire charter experience was great. The crew were great, the boat was great, and we would look to you guys again should we do another charter. Thanks.

Ken H, aboard Catamaran London Sky, June 2017 sailing the Virgin Islands

The trip for all of us was 10/10!

The crew of Ed and Kat were so friendly to our family. We never felt that we were bothering them if we need something. They engaged us throughout the trip in conversation that was really enjoyable.

The ship was in great shape and just enough space for everyone. The favorite spot for the family was at the front sitting on the seats at the tip of each bow as it sailed.

the food was great and Kat did an A1 job on the girls that were eating gluten and dairy free. The grilled meals by Ed were great. Trying the new seafood was awesome for us all.

The sailing destinations were great and the itinerary flowed well for us. Moving to a new place each day was a great adventure each time. I appreciated Ed and Kat guiding us about what to expect getting off the ship with taxis, places to see and eat at, or views to make sure we saw.

Sailing directions was very helpful in the planning of this trip and the website is good.

We would love to sail again in the future. Our family cannot stop telling others about how great the trip was for us all.

Jerome G, aboard Catamaran Ultimalife, June 2017 sailing the Virgin Islands

Everything was AWESOME! LOVED Matt & Kendra and the boat/trip couldn’t have been better.

Anna A, aboard Catamaran Zephyr, June 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.