Crewed Caribbean Yacht Charters
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 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:

> See all Specials and Discounts
Save 10% on London Sky's charter rates for 5-night or longer charters sailing the Virgin Islands or Grenadines.
Available for charters starting 28 March 2016 through 7 August 2016
Reservations need to be confirmed before 9 July 2016
Save 5% aboard Blue Moon sailing the Virgin Islands this winter and spring. Additional bonus: free shuttle transport from the airport or your hotel and 3 dives for certified divers.
Available for charters starting 1 April 2016 through 10 June 2016
Reservations need to be confirmed before 17 May 2016
Save an incredible 20% on charters sailing in 2016 in the Caribbean. Excludes Christmas and New Years weeks.
Available for charters starting now through 17 December 2016
Reservations need to be confirmed before 31 March 2016
Expires in 48 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!

Latest crewed yacht charter Reviews

> See all of our crewed yacht charter Reviews

Ben and Rachel were wonderful. A perfect match for our group. Extremely knowledgeable, friendly , accommodating , attentive, responsible , trustworthy , and safety conscious. We loved getting to know them and were very comfortable with them. They were very professional, yet warm and personable. They treat each other with great respect and kindness. We would definitely charter with them in the future. They spoiled us from the first minute.

We loved the Soterion. Very clean. Very comfortable. Well ventilated and loved the air conditioning at night. Ben and Rachel kept the ship well organized and everything had its place and the laundry and towels smelled great!!!! Favorite aspect was every room had at least a queen bed and its own bathroom and I loved that there was sunscreen, shampoo, conditioner and lotion on board. A smooth ride as well.

The food was fabulous ! Like 5 star restaurant ! Rachel is an awesome chef and always kept the kitchen clean and great hygiene. We all were so stuffed with food each day but we couldn't say no to any meal because they were all so yummy! Very impressive. The duck was one of the best entrees I have ever had.

The itinerary was perfect. Enjoyed every place we went. Every stop was different and unique and had something to offer. Ben did a great job. Loved the map, hat and T-shirt we received at the end of the trip.

Sailing directions was very prompt and helpful. Ben and Rachel has nothing but compliments for John Lane and said I chose one of the best services and I completely agreed! Emails were answers immediately, no matter if it was day or night or weekend. I will definitely let my friends and family know of Sailing Directions. We would like to book another charter in the future.

Thanks again for everything. It was a fantastic experience!

Lana S, aboard Catamaran Soterion, February 2016 sailing the US Virgin Islands

We enjoyed sailing around and exploring St. Maarten, Anguilla and St Barts. This charter area offered more sailing opportunities than the BVI. The BVI was a better destination for iconic beach bars, easier hiking, and clearer snorkeling.

Nick & Lucy are awesome crew and frequently knew what we wanted before we even had a clue. I love them both.

Best Revenge 5 is very comfortable, well maintained, and spotless. My favorite things about the yacht are warm fresh water for rinsing off after swimming, comfortable beds, individual AC thermostats in cabins, robust shower in cabin, extensive music selection, and crew's attention to detail.

Lucy exceeded our expectations once again. She is a very talented and creative chef with a passion for food preparation & presentation. She went the extra mile to accommodate our individual preferences and dietary needs.

Sailing Directions service was prompt and efficient. Keep up the good work.

Susan V, aboard Catamaran Best Revenge 5, January 2016 sailing the Caribbean Leeward Islands

Stephen & Julia are extremely knowledgeable - very, very accommodating - they sat down with us and listened to our requests, thoughts, etc. to make a plan for the week - and then each day the schedule was addressed and our requests were foremost in their decisions as to what to do. We felt like they had all the knowledge of what we’d like to do and when, and they put together great itineraries.

Safari exceeded our expectations - plenty of room, lots of area to gather, or to be alone. Beds were really comfortable, and everything was so clean.

The food was beyond our expectations! Julia is an amazing cook - delicious and gorgeous presentation! She customized to us - only complaints are that she fed us too much and that we had to come home without her!

We felt like we did the perfect option with the half board - the benefit of Julia’s amazing cooking, and also being able to sample some of the local flavor at dinners and lunch.

We had an incredible time - exceeded our expectations in every way! Thanks to you too for coordinating for us - made everything run very smoothly. We really appreciated the advice regarding packing - we did a pretty good job with that. Pre-planning and prep was great and easy. Will definitely recommend to others! And we’ll be back, too!

Betsy G, aboard Catamaran Safari, January 2016 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.