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 winter weather to white sandy beaches, consistently light Caribbean trade winds, clear blue water, customized gourmet dining and fresh cocktails, islands grouped close for great day sailing, world-class dive sites, award winning yachts and crew, and sunshine every day of the year.

Sailing Directions® helps you book a crewed yacht charter in the Caribbean Virgin Islands, Leeward Islands and Grenadines. We will match you with a charter yacht that best fits your budget and needs; from an all-inclusive family or couples sailing vacation to a corporate incentive party or an unforgettable honeymoon or anniversary charter. We make the booking process easy and, via our website and experienced charter brokers, provide a wealth of information and support to help you prepare for your trip and get the most out of your yachting vacation.

Sailing Directions is an independent crewed yacht charter brokerage which has been in business since 2005 with access to an extensive range of crewed yachts. When you book a private crewed yacht through us you get peace of mind that our advice is unbiased and your payments are held in a secure 3rd-party escrow account until the charter date. We also accept credit card payments through our secure website.

We specialize in crewed catamaran charter vacations sailing the Caribbean Virgin Islands. We have firsthand knowledge of the boats and crews and have broad knowledge of the Virgin Island cruising areas.

Start your search now using our live online availability search form now or contact us to start planning 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:

Details and Conditions:

- Available for 1-8 passenger charters, using 5 cabins. 6th cabin not available on this special.

- BVI cruising grounds only.

- If you fly to St Thomas, land taxi & private water taxi to BVI will be arranged and is included in price.

- Fully air conditioned boat, running 24 hrs a day, each cabin has their own unit so client can control their temperature.

- All fuel is included.

- All food and drinks are included with exception of two dinners and two lunches to be taken ashore at client expense.

- Each cabin has its own private en-suit head with a waterfall shower and king sized walk around bed.

- Rendezvous diving & deep sea sport fishing can be arranged at client expense.

- 15-20% Crew gratuity not included.

Dates:
Available for charters starting now through 1 November 2017
Reservations need to be confirmed before 22 September 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. EXCLUDES: Christmas and New Years weeks.
Dates:
Available for charters starting now through 31 August 2017
Reservations need to be confirmed before 1 August 2017
Expires in 5 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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We had a fantastic time. It was a trip of a lifetime and we are well traveled.

The food was spectacular. Many meals were among the best we have ever enjoyed.

Our favorite aspect of the yacht was the upper deck.

We saw and did everything we had hoped.

Gene B, aboard Catamaran Tobarths, July 2017 sailing the Virgin Islands

Spending a week sailing with Rich and Lisa was a fantastic experience. Without a doubt, it was the best trip my family has taken together, ever.

Sabore is immaculate with great space and comfortably accommodated my family of eight.

The food was unbelievable gourmet and abundant in proportions.

Lisa was most hospitable and organized which enhanced the efficiency of the trip. She took care of our every need.

Rich knows the waters and quiet anchoring spots to avoid the crowds. The water sports were cool and the diving and snorkeling fantastic.

John Lane at Sailing Directions was professional and well organized. He responded immediately to my questions about logistics. Most importantly, he identified a wonderful boat and crew.

Bottom line- Lisa and Rich are two wonderful people who will provide your family or friends a great experience.

Fred M, aboard Catamaran Sabore, July 2017 sailing the Virgin Islands

Everything was ABSOLUTELY INCREDIBLE! We loved every minute of it! Cliff and Christian were perfect. The food was all healthy and delicious and she managed to satisfy even my very picky kids. Cliff was basically a camp counselor with the kids, taking them tubing umpteen times or even just for dinghy rides.

Stop Work Order was beautiful, clean, comfortable, and had so much room for everyone! The yacht had everything each one of us needed. AC (with individual thermostat controls in each room) was cold and on all the time. It also has a great water maker so everyone was able to take long, hot showers whenever we wanted.

It was perfect! I would recommend the boat, the crew and the itinerary to anyone, without hesitation. Just wanted to let you know that I have said it was the best vacation ever!<

Beth S, aboard Catamaran Stop Work Order, July 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 and monohull sailboats 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.