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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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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
Available for charters starting now through 14 December 2018
Reservations need to be confirmed before 16 November 2018
Save 10% off new 7-night reservations sailing in 2018. Special excludes Christmas and New Years dates.
Available for charters starting now through 15 December 2018
Reservations need to be confirmed before 1 November 2018
Save 10% off new 7-night reservations sailing in 2018. Special excludes Christmas and New Years 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

> See all of our crewed yacht charter Reviews

Soterion was awesome but even more so was Ben and Rachel. They really made the trip for us amazing for us. We could have been on a dingy and the trip would have been amazing because of them.

Ben and Rachel were amazing. I truly would call them friends after this trip. They were extremely friendly and very knowledgeable of sailing, and all things BVI. They truly knew how to accommodate us based on our likes, dislikes, and level of activity based on our personalities. This is a vacation where one could really relax knowing that everything was handled by Ben and Rachel.

Soterion was very clean, all rooms well ventilated with air conditioning. The best part of Soterion was how roomy it was. I worried about 10 humans living on a 57ft catamaran for 7 days. It never felt crowded and there was always some place to go if you need to be alone.

Rachel is a great chef. She was able to accommodate special diets and make each of their dishes to their liking. Every meal from breakfast to dessert in the evenings was great.

We loved that Ben and Rachel were so experienced. We are an active bunch and the itinerary was customized to those activities. The entire group liked the evening "family" meetings we had with Ben and Rachel to discuss the next day's activities and adjust based on our feedback.

The entire group was very satisfied with Sailing Directions planning and commitment. This was our first sailing charter, we had many questions which John and the Sailing Directions website answered. Very impressed, we knew exactly what to expect from packing our lightweight luggage to water taxis to hotel recommendations prior and after the sail. We are discussing another charter for the end of next year.

Marcos T, aboard Catamaran Soterion, May 2018 sailing the British Virgin Islands

Ryan and Jill were awesome. In the 2 weeks leading up to our arrival Jill was in regular contact with our whole gang on little details from food, drinks and activities. They even got a coconut tree for us to plant on an island.

We enjoyed the entire boat from the trampolines, hanging out front under the sun shade and chilling on the back of the boat.

I am certain there is no other crew that was as prepared food-wise as these guys. I am not sure how many cruises I have been on but it probably more than 24. If I took the best meals from all of those cruises, it wouldn't come close to the food that we ate last week, not even close!

Our charter broker, John, was very responsive the whole time. We will definitely book another trip in the year or 2.

Kevin B, aboard Catamaran White House, May 2018 sailing the Virgin Islands

Matt and Dana (standing in for Casey) were stars. They were more than friendly they were like family. Matt's knowledge of the islands, special stories and the history were amazing. They accommodated our gluten-free needs as well as fresh and healthy with flavors Galore and presentation of a Michelin meal. The breakfasts were exquisite with poached egg on portobello mushrooms to spectacular Portuguese sausage and Spanish omelets.

Matt encouraged us, with little bit of a nudge, to try things that we were a little apprehensive to do but we're so thankful that he did.

The Virgin Islands were way beyond our expectations. Matt knows his stuff when it comes to balancing each day with as much as you could possibly do and yet fully enjoying each moment.

This was a bucket list trip but because Dana and Matt made it beyond our expectations we have high hopes to repeat this vacation. We are fortunate to be youthful in our late 50s and 60s and this trip reconfirmed that we want to continue to push and enjoy this part of life.

Robert H, aboard Catamaran Island R&R, May 2018 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.