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.
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.
Jill and Ryan were unreal. Best vacation experience we have ever had - largely due to their considerate demeanor coupled with their incredible knowledge of boating and the local geography. They were like an aunt and uncle to our boys - they loved spending time with them.
Great boat - our favorite part of the yacht was the master stateroom - luxurious!
I was amazed at the food Jill was able to produce given the limited galley she had to work with. We looked forward to eating every meal.
The itinerary was perfect - we were constantly on the go. We loved the choice spots we had to anchor to in the evenings.
I thought you did an excellent job from start to finish. Thank you! We will be sure to recommend you to anyone who asks us about our trip.
Ryan and Jill were outstanding hosts - they made our first extended boating experience exciting and a true pleasure. Not an easy task given that we had 3 boys ages 6, 10 and 13.
Scott M, aboard Catamaran White House, July 2018 sailing the Virgin Islands
We must say that the trip was absolutely spectacular. Everything was great and both Michaela and Andrew were outstanding. Michaela a Master chef and scuba diving teacher and Andrew a true and passionate Captain.
The food was delicious and very well presented. The variety of dishes was very impressive. Michaela is a true Master Chef. It was most of the time adjusted to our preferences.
We would love to do this trip again and we have already given the link to sailingdirections.com to many of our friends. We highly recommend Sailing Directions.
Great team Andrew and Michaela, Scuba Dives that were one of the most beautiful our divers had seen. We appreciate that the food, drinks were very generous. Thank you so much for all your help on this trip.
Monica A, aboard Catamaran Flip Flop, July 2018 sailing the Virgin Islands
Absolutely the best vacation we have ever had! We Loved Loved Marcus & Risa! Between the two of them I’m not sure who knew more about every place we went. We Highly recommend Neverland to all our friends & family!! John did a wonderful job and was always responsive to ALL my emails. We would love to book and go again!
Leslee M, aboard Catamaran Neverland, June 2018 sailing the Virgin Islands
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.