Crewed Caribbean Yacht Charters

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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, 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 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 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. 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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Save $500 off the listed rates for any 7 night reservation for available dates in 2016 and 2017. Prorated discount for fewer than 7 nights.
Available for charters starting 6 November 2016 through 31 December 2017
Reservations need to be confirmed before 1 January 2017
Save 5% off the regular charter rate for bookings confirmed aboard Akasha before the end of the year.
Available for charters starting now through 15 December 2017
Reservations need to be confirmed before 31 December 2016
10% discount and a free sleep aboard the night before your charter starts. Boarding after 4pm, cocktails upon arrival, dinner ashore (not included), then breakfast aboard the next morning and extra half day charter time! Minimum of 5 night charter and excludes holidays.
Available for charters starting now through 31 May 2017
Reservations need to be confirmed before 15 December 2016
Expires in 49 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.

> See all of the current crewed yacht charter Specials and Discounts!

Latest crewed yacht charter Reviews

> See all of our crewed yacht charter Reviews

Brendon & Anastasia were an awesome crew and we clicked immediately.

The food was probably the highlight of the charter. Anastasia is an incredible chef (not just cook). She took our requests and nailed it.

We saw everything we asked for and even a few new spots that were really cool. The channel beside Lovango Cay was incredible. Great breeze, awesome snorkeling. Redid our 25th anniversary wedding vows on beach at Hawksnest - complete surprise for all. Brandon and Anastasia helped coordinate flowers, video, stand-in best man..

Sailing Directions was a great liaison, worked on making it affordable, paperwork was easy and communications were great whenever I had questions either online or phone. Keep up the great work!

Mark F, aboard Catamaran Pisces, August 2016 sailing the Virgin Islands

The crew was friendly, knowledgeable, attentive and accommodating. I cannot sing my praises high enough for Adam and Tina. Adam was a highly skilled captain with excellent knowledge of the area we cruised. He knew when and where to go for drift snorkeling, and as a result our snorkeling experience was better than any previous trip. Tina was a friendly and joyful host.

The Rubicon was comfortable, clean and well ventilated. I liked the fact that each cabin had its own head. The Rubicon was the perfect mix of performance and comfort.

Tina was a great hostess and cook. I ate better on the boat than I eat at home. Tina manages the difficult mix of preparing food the tastes, great but is healthy as well. I usually put on weight during vacation and did not on this one, but I ate like a king. Fresh baked bread,muffins and much more.

The Exumas this time of year is just amazing. I have traveled the Caribbean for many years and the best beaches and water is in the Exumas. The crew has cruised these waters for many years and they have extensive knowledge of where to go and what to do. Adams was well connected with the local people and this made for a great experience. A real bonus of going this time of year (July) is that no one is there. We had all the beaches and anchorages to ourselves.

Very happy with Sailing Directions’ service.

Ernie L, aboard Catamaran Rubicon, July 2016 sailing the Bahamas

Paul & Isabella were wonderful. Very professional and knowledgeable. They made our vacation a memorable one.

Something Wonderful is beautiful. Clean, great layout. Love the light grey tones. Very serene.

Super impressed with the food. Bella is extremely talented. There was not a meal that we didn't enjoy. It was actually hard to pick just one as our favorite.

We loved the itinerary in the BVIs. Had a good mix of beach and snorkeling and watersports.

John at Sailing Directions did a great job of getting back to us with any questions we had before and after booking. Very professional.

We had been looking forward to going back to the BVIs with our kids since we loved it so much the first time we went. It was as beautiful as we remembered. Our children really enjoyed the vacation. Great family time. The boat was even nicer in person than online. It is very spacious. Has plenty of space to get sun if that's what you want or shade if you prefer. The fly bridge is incredible. Gives you so much extra room to lounge around. The color scheme is very soothing. It is super well-kept and clean.

Paul and Bella are incredibly professional, friendly, attentive and accommodating. They made our vacation memorable from start to finish. Paul is very knowledgeable of the islands. We loved everywhere he suggested we try. Bella is an incredibly talented chef. Every meal was amazing. We looked forward eagerly to each one and to this day have a hard time picking our favorite. If we were to return to the BVI's again we would without hesitation book Something Wonderful. My suggestion to anyone looking to charter. Look no further. Book this boat ASAP. You will not regret it.

Patty M, aboard Catamaran Something Wonderful, July 2016 sailing the British 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, 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.