Availability Search

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 offshore 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 or couples group sailing vacation to a corporate party or an unforgettable honeymoon or anniversary charter. 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 and price point. 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:

> See all Specials and Discounts
Details:
$2,500 per week discount for any new charter sailing in 2017. Discount does not include one appetizer and dinner (you'd dine ashore for this).
Dates:
Available for charters starting now through 15 December 2017
Reservations need to be confirmed before 1 November 2017
Details:

5% Earlybird discount off the listed rates for charters sailing between 1 December 2017 and 1 August 2018 - that 's right, a year from now - Book early and SAVE!

Does not include holiday weeks.

Dates:
Available for charters starting 1 December 2017 through 1 August 2018
Reservations need to be confirmed before 29 April 2017
Expires in 32 Days
Details:
15% off any charter taking place from now until 31 March 2017 sailing the Grenadines.
10% off any charter taking place in April 2017 sailing the Grenadines, Leeward Islands or Virgin Islands.
Valid on new bookings only. Inquire for less than 7 nights..
Dates:
Available for charters starting now through 30 April 2017
Reservations need to be confirmed before 1 April 2017
Expires in 4 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!

Bermuda 2017 America's Cup

Charter a Crewed Yacht at the Bermuda 2017 America's Cup

Latest crewed yacht charter Reviews

> See all of our crewed yacht charter Reviews

Our crew, Jackson and Chelsea were fantastic. They were very knowledgeable, professional and friendly. They shared information about the islands and Chelsea's food was healthy and delicious.

Sweetest Thing was more spacious than we expected. It had A/C although we opted to keep our port hatches open for the fresh air. It was clean. We were traveling with 2 kids and it was nice they each had their own cabin and their own bathroom, each with a shower. The whole yacht was kept clean and tidy.

The food was perfect. We enjoyed every snack, entree and dessert. Chelsea always added a little something to add to the presentation. It matched our preferences perfectly.

The itinerary exceeded our expectations. We covered more territory than expected. We could relax comfortably in the sun or shade while sailing. And every stop had something a little different to offer. Jackson informed us of our choices and we were always happy we took his advice on what to do.

Thanks for your help. We had a fantastic trip!

Carolyn B, aboard Catamaran Sweetest Thing, March 2017 sailing the Virgin Islands

Matt and Kendra were amazing! They really took the time to plan a great itinerary taking into consideration what everyone wanted to do during the trip. There were 8 of us (4 couples) so there was a lot to consider. We've all done charters in BVI in the past and they did a great job ensuring that we saw some new places and were able to enjoy some of our favorite spots.

Matt is a very capable Captain and everyone felt safe with him at the helm. Kendra is a fantastic chef and the food she prepared was delicious! They both worked very hard to ensure everyone was taken care of and had a great time. They are such a hardworking crew. We were totally impressed.

Zephyr is a beautiful yacht. It was spotless and well ventilated. Everyone was incredibly comfortable. The outdoor seating was great and was so important to all of us. That is what really sold us on the Zephyr was the amount of great outdoor seating. You spend most of your time on deck and we wanted to be comfortable - and it was. There was plenty of space for all 8 of us whether we all wanted to be together or needed some downtime.

We appreciated the amenities the owners purchased. The memory foam on the beds, the Jura coffee maker, the paddleboards, kayaks, etc. The kitchen was so well equipped which made the meals Kendra prepared just amazing. Matt and Kendra kept the boat clean and organized throughout the trip.

Kendra did an amazing job of catering to everyone's likes/dislikes. Half the group are really picky eaters and they were very happy with the food and the extra time she took to ensure they ate well. Every meal was beautifully presented, and just delicious. We only ate dinner onshore once and it was not very good compared to Kendra's cooking.

Matt and Kendra did a great job taking us to places we have not seen before and were not crowded with tourists. They really paid attention to what we wanted to do and to see. We were 100% satisfied with our itinerary.

Sailing Directions did a great job thorough out the process. This trip on the Zephyr was amazingly relaxing and we did not have to think about anything, plan, cook, or clean. Matt and Kendra were so attentive, we ate so well and the bar was very well stocked.

Lindi R, aboard Catamaran Zephyr, March 2017 sailing the Virgin Islands

The trip was incredible.

Matt & Kendra could not have been more accommodating. Matt's sailing ability and knowledge was incredible, I felt extremely safe with him at the wheel. He amazed me at times maneuvering through some very busy moorings, what a pro! Kendra's cooking was awesome, so very good, perfectly presented. Kendra was more than accommodating and would go out of her way to ensure we were all well taken care of.

Zephyr was perfect, just what we had wanted. The upper deck seating was important to us and provided our group with a perfect place for friendly conversation, cocktails and sunning while we sailed. The rooms were spotless and air conditioned, we could not have asked for more.

The food was professionally prepared, Kendra is a pro. Her presentation of each meal was that of a 5 star restaurant. Kendra went out of her way to ensure that everyone had plenty to eat. Her appetizers were out of this world.

The itinerary that Matt planned for us was so much more than we expected, he went above and beyond. We wanted to see off the beaten path areas. Matt took us to places that were less traveled. Our favorite place was Anegada.

Cindy & Steve M

Lindi R, aboard Catamaran Zephyr, March 2017 sailing the 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.