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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10% discount through August 2016
Special introductory offer for the brand new Lagoon 560 catamaran Amazing Blues. Save 10% on any reservation for 6 nights or longer confirmed prior to 1 January 2016 for charters sailing by 1 August 2016. This discount does not apply to Christmas or New Years weeks.
Available for charters starting now through 1 August 2016
Reservations need to be confirmed before 1 January 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 now through 1 August 2016
Reservations need to be confirmed before 31 December 2015
15% Discount 25 Nov - 17 Dec 2015
Save 15% on luxury Lagoon 560 Copper Penny between Thanksgiving and Christmas this year sailing the VIs.
Available for charters starting now through 17 December 2015
Reservations need to be confirmed before 30 November 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

> See all of our crewed yacht charter Reviews

Overall the trip on a scale was a 9.5 out of 10. I just don’t believe in perfection but the charter exceeded our expectations.

Let’s start with the Crew. Bertrand, Lorianne and Matthew (Chef) were incredible. They actually made the trip. The sailing, islands, waters and beaches were amazing but if it had not been without the three of them the trip would have been par. Seriously they made the trip. When we thought the food could not get better Matthew blew us away with a something magical. The crew was all French, and although there were language barriers at times, we never let our 1st languages get in the way of figuring out how to communicate. Let me get to the heart: we all cried when we departed. Seriously they were crying and we were crying because of the bond we created over the trip. We are already planning our next charter for 12+ days.

Bertrand (Captain) was solid. Confident without being egotistical. He ensured that were safe at all times, and planned each day’s journey. Lorianne was a sweet heart and made everything very comfortable for all of us.

The beaches, waters, snorkeling, swimming was as amazing. It was an amazing 50th Birthday week.

, aboard Catamaran Arion, November 2015 sailing the Caribbean Grenadines

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

> 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, 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.