Crewed Caribbean Yacht Charters

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 and sunshine every day of the year.

Sailing Directions® helps you find and reserve a crewed yacht charter in the Caribbean. 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 yacht charter broker with an extensive range of crewed yachts and a depth of expertise. 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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$1,000 discount for charters sailing by 1 August 2016
$1,000 discount on 7 night or longer charters sailing aboard Ma Ha in the Caribbean Virgin Islands. An additional $500 discount is available for charters beginning by 1 December 2015.

Available for charters starting 12 November 2015 through 1 August 2016
Reservations need to be confirmed before 1 July 2016

10% Discount through August 2016 in the Virgin Islands
Save 10% off the regular charter rates for any charter booked before the end of 2015 and sailing any available week before 1 August 2016 (including 2015 Thanksgiving and Christmas weeks!), in the British and US Virgin Islands.

Available for charters starting 17 October 2015 through 1 August 2016
Reservations need to be confirmed before 31 December 2015

Currently available for Christmas and New Years weeks
7 night charter $32,500 all-inclusive for up to 6 guests over Christmas or New Years week sailing the Virgin Islands or Leeward Islands. Stunning, fast crewed Gunboat catamaran.

Available for charters starting 16 December 2015 through 9 January 2016
Reservations need to be confirmed before 29 October 2015

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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Stephen & Julia were top notch. We enjoyed not only their professionalism and great ideas about where to go and what to see, but also their stories and meeting good friends of theirs along the way. They really made the trip memorable and relaxing. It was clear from the minute we stepped on Safari that we had chosen a great crew, but by the end of the week we had also made new friends.

Safari was perfect, in excellent physical condition and perfectly laid out for our family of 4. We loved the front sitting area to relax with great views while underway and the rear table and sitting area was perfect for not just meals but gathering for games and cocktails.

The food was great. Julia made lots of different dishes and we enjoyed them all. We didn’t have a lot of specific preferences and were very happy with all of her cooking. Come hungry as there’s always lots to eat and drink.

We loved the itinerary sailing the Virgin Islands. We liked the route and all the moorages but what really made the trip special was Stephen & Julia’s local knowledge. They showed us a handful of small beach towns and the local vibe of each place. We met a number of their friends and really enjoyed seeing some of the spots off the beaten path.

Sailing Directions was great. Everything was easy and all my questions were answered promptly. The website and information shared for what to pack, where to stay on St. Thomas, etc. was very helpful.

, aboard Catamaran Safari, August 2015 sailing the US Virgin Islands

Eric and Kristen were AMAZING and they made our trip worthwhile. They very friendly, knowledgeable, attentive and VERY accommodating with all the needs of our family. They went out of their way to make sure that we were happy at all times, and doing things that we liked to do. They included us in the decision making of all our activities, and I have to say that they were spot on with the suggestions that they made for our active girls. They engaged well with our girls who seemed very comfortable with them. My husband was thrilled to have an opportunity to fish during our trip. Eric made sure to have all the fishing gear for him. He was thrilled when he caught a Spanish Mackerel and Kristen prepared it for our lunch. It was outstanding!

We loved One Love and we thought it was very comfortable and clean. We enjoyed spending time in the common areas with Kristen and Eric especially at night when we sat together to eat, play cards and share stories. We loved sitting in the trampoline as we enjoyed the sailing from island to island or watch the gorgeous sunsets.

We look forward to each one of our meals as they were all delicious! The presentation was creative and beautiful. The menu was outstanding and we were very happy that we chose to eat all our meals from Kristen. We particularly enjoyed the variety of food that we had every day including the drinks. Our freshly caught fish was on the table within the hour, pretty impressive!

We enjoyed our itinerary very much. We loved every island that we visit. We particularly loved Bitter End, Savanah Beach, The Baths, and The Indians (fabulous snorkling!). We all enjoyed having the opportunity of kayaking, tubing, paddleboarding and snorkling. We were very lucky with our snorkling as I think that we saw about everything we could imagine (sharks, dolphins, turtles, seahorses, barracudas, etc.). Eric and Kristen seemed very knowledgeable about what activity to do in each area.

We are very happy about the recommendation that you made about the crew. Eric and Kristen exceeded our expectations and they were a perfect match for our family.

We would love to charter another catamaran at some point as it was the Perfect Vacation in Paradise. The catamaran was a perfect size for our family with kids however I would recommend a slightly larger boat for a group of adults.

Perfect family vacation! Thank you again for all your assistance and we will make sure to recommend you, One Love and the crew to all our friends. We look forward to another trip to PARADISE in the future!

, aboard Catamaran One Love, August 2015 sailing the US Virgin Islands

Tim and Stephany were tireless, helpful, interesting and sensitive to our needs. We could not have asked for a better crew. Their warmth, knowledge and willingness to share insights into their lives made the trip a very satisfying adventure. We have never received so much attention.

It is clear they take great pride in Endless Pleasure as it was very clean, well maintained and ready to sail under all kinds of conditions. The steady winds in the Grenadines and many hatches combined to keep the boat well ventilated. Air conditioning was turned on when needed and worked very well.

We have never had a full time chef before – what a great experience. Third crew member JoJo continually worked to anticipate our needs and was more than willing to accommodate our diverse dietary requests. Collectively, they provisioned the boat with foods and drinks that we requested after spending an hour with us on the phone in advance of the trip. JoJo’s fusion expertise made many memorable meals and the rum punch was a crowd pleaser.

The itinerary evolved as we gained experience with the area and the opportunities available. We watched a leatherback turtle crawl up on the beach, dig a hole, lay her eggs, cover them up and head back out to sea. We caught tuna and ate sashimi. Tim & Steph did all the work laying out the line, cleaning the fish and handing off the meat to JoJo to apply her magic. We went snorkeling in many places, and went ashore to explore numerous islands, which led to a pattern of snorkeling, sailing, fishing, anchoring, exploring and sometimes waterskiing, paddle boarding and tubing. They took pictures of us as a family in many places and gave us the file with the pics at the end of the trip.

This is our first experience with chartering and we were unsure about the process and what to expect. It turned out to be a very straightforward process and John’s advice about what to expect and effort to facilitate contact with Endless Pleasure was very helpful. We will pass on information about Sailing Directions and Endless Pleasure to friends that are interested in sailing.

The end of the charter came too quick, we felt that we were just getting into a rhythm and could have spent many more days with Tim and Steph. We are interested in staying in touch with them and following their adventures and hope that our paths cross again.

, aboard Catamaran Endless Pleasure, August 2015 sailing the Caribbean Grenadines

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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.