Crewed Caribbean Yacht Charters

Search for Crewed Charter Yachts available for your dates:

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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Reduced Christmas week rate
Yes Dear is offering a reduced Christmas week rate of $28,000 for up to 10 passengers for 7 nights sailing the BVIs. Charter must end 12 noon on 26 December or earlier.

Available for charters starting 10 December 2015 through 26 December 2015
Reservations need to be confirmed before 16 November 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

15% discount through November 2015
Save 15% on Lady Katlo's charter rate for any reservations taking place between now and 5 November 2015. Lady Katlo is available in the BVIs through late May and sailing in the Grenadines from mid June.

Available for charters starting now through 5 November 2015
Reservations need to be confirmed before 1 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

> See all of our crewed yacht charter Reviews

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

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

Roland and Vanessa know exactly what they’re doing and do it all with grace, humor and kindness. They were delightful to adults and teenagers alike, no small feat!

Everything on Flow is as comfortable as it can be. Our favorite aspect is that the yacht is big enough to provide many different areas to hang out so, despite having 9 of us (plus Roland and Vanessa), including five teenagers, no one felt crowded or cramped. We even kept offering to let the teenagers off the boat to go to restaurants and bars on shore by themselves and they consistently declined to leave!

Vanessa is a gifted chef. Seriously. We’ve had other experiences being cooked for in this way and she was the best ever.

If you are considering a vacation on a yacht crewed by Roland and Vanessa, just do it! You absolutely will not be disappointed! They are fun, kind, knowledgeable and incredibly service-oriented. Everyone loved them and would sail with them again in a heartbeat.

, aboard Catamaran Alive, August 2015 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.