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Experience the vacation of a lifetime aboard a luxury, all-inclusive, professionally crewed catamaran, sailing or power charter yacht in the Caribbean.

Escape to white sandy beaches, consistent Caribbean trade winds, clear blue water, customized gourmet dining and fresh cocktails, sheltered islands grouped close enough 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 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.

Find your ideal crewed yacht 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:
Lir is offering 2018 discounts of 15% off for 7 night charters between the following dates:
28th May - 13th June 2018 in the Bahamas and
16th August - 28th August 2018 in the Windwards/Grenadines and
20th October - 14th December 2018 in the Grenadines or Virgin Islands
Dates:
Available for charters starting now through 14 December 2018
Reservations need to be confirmed before 16 November 2018
Details:
Save 10% off new 7-night reservations sailing in 2018. Special excludes Christmas and New Years dates.
Dates:
Available for charters starting now through 15 December 2018
Reservations need to be confirmed before 1 November 2018
Details:
Save 10% off new 7-night reservations sailing in 2018. Special excludes Christmas and New Years dates.
Dates:
Available for charters starting now through 15 December 2018
Reservations need to be confirmed before 1 November 2018

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!

Latest crewed yacht charter Reviews

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Matt & Dana (Dana filled in for Casey) were very friendly and clearly knew what they were doing. Matt’s knowledge of the islands led us to many places others may not have the opportunity to experience and we took home several recipes and ideas from Dana’s cooking. My 83 year mother traveled with us and Matt & Dana were very patient and willing to help her so she had a wonderful experience.

We found the boat very comfortable for 6 people and the crew. We really only slept in the cabins, but they were big enough to sleep well. We had plenty of space on the deck, whether we were up front when sailing or sitting in the back for dinner/lunch. The boat is a little bit older which we knew going in but is well maintained and very comfortable.

The water toys really added to the experience, wake boarding, snorkeling, paddle boarding, the go-pro and Peggy & Ursula made sure we had plenty to do in the water.

The food was fantastic, really nice variety and plenty to eat. Dana did a great job creating menu options for my vegan daughter who probably had more variety on the boat than any other time. Very locally focused, which was nice in terms of experiencing new tastes.

Eddie Y, aboard Catamaran Island R&R, June 2018 sailing the British Virgin Islands

Michaela and Andrew could not have been more friendly, knowledgeable, attentive and accommodating. Spending six days and nights in relatively tight quarters was managed to perfection by those two. They were in sync the entire time and worked like a well-oiled machine. They were so comfortable and pleasant to be around.

Flip Flop was a great boat. They kept it immaculate throughout the duration of the trip.

We did not have a bad meal on the boat. Truth be told, we didn’t have a meal that was any less than fantastic. We had one meal on land and regretted it. The whole time we said things like, “Michaela would do a much better job than this. Michaela makes a better cocktail than this. Michaela’s presentation is world’s better than this etc.”. The food was plentiful but not gigantic portions. We loved that. Also, it was all so fresh and beautifully plated. It was obvious that she had carefully read about our preferences and tailored her menus accordingly.

The itinerary was perfect. Just the right combination of movement, beaches, snorkeling, bars, etc.

Sailing Directions website is absolutely fine and easy to navigate. John, you did a great job. Specifically, you always got back to me quickly which I appreciated.

Additional comments: I want to say something about Andrew and Michaela and their relationships with my kids. A bonus that I only realized after our week was the relationship established with our kids and those two. For my 24 year old son, Andrew was a cool respite from dealing with the estrogen of his sisters. They played games, read the same book, and simply had a nice time together. For my 22 and 19 year old girls, they saw in Michaela an interesting, smart, capable young woman pursuing her dream and being an equal and complimentary partner to her guy. I treasure that part of our vacation.

When you chat with Andrew and Michaela, please pass along our gratitude.

Joyce F, aboard Catamaran Flip Flop, June 2018 sailing the Virgin Islands

Everyone in our party felt like we had the best crew in the Caribbean in Marcus and Risa. Our daughter received a marriage proposal at the Baths and Marcus and Risa really made it special.

We liked that Neverland’s en-suite bathrooms, the upper seating area and the fact it was a new boat.

Risa is a magician. Still not sure how she produced 3 award winning meals a day for 9 people in the tiny galley! And without re-provisioning during the charter.

Marcus has a deep knowledge of the area and hit all the highlights we hoped for.

Communication was excellent from Sailing Directions. John did a great job helping us through the impact of the hurricane.

I wouldn’t hesitate to recommend Sailing Directions and Marcus/Risa/Neverland.

Chris P, aboard Catamaran Neverland, May 2018 sailing the Virgin Islands

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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.