Book an unforgettable crewed yacht charter vacation.

View Available Yachts:

Book with the Caribbean specialists. For over 13 years we have been a leading yacht charter brokerage connecting groups like yours with the best crewed yachts available for charter in the Caribbean including the Virgin Islands & BVIs, Leewards, Grenadines and Bahamas.

Utilize out firsthand knowledge about available charter yachts, crews and locations to book the best yacht and crew for your budget and travel style.

Start planning your vacation today!

Sail away to white sand beaches, consistent Caribbean trade winds, clear blue water, sheltered island bays great for cruising, world-class dive sites, award winning yachts and crew, and sunshine every day of the year.

crewed catamaran charters


Catamarans offer stability and space, providing an excellent charter vacation platform. The accommodations are separated fore and aft and between hulls. The cockpit is wide and comfortable for dining with family and friends. Many catamarans feature a flybridge level, great for additional lounging and viewing.
View catamarans
crewed sailboat charter


Monohulls offer a traditional sailing experience for active sailors. Monohulls are available in various sizes for various budgets and are generally ideal for smaller parties. They heel under sail and offer all the action of a true sailing vessel. Sail the Caribbean Tradewinds.
View monohulls
crewed power yacht charter

Power Yachts

For the ultimate experience in luxury and comfort, a power yacht or super yacht offers a high crew to guest ratio, individually designed capacious interiors, highly customized, professionally prepared menus and the option to head to your next destination swiftly and style.
View power yachts
Experience the vacation of a lifetime aboard a luxury, all-inclusive, professionally crewed charter catamaran, sailing, or power yacht in the Caribbean.

Specials and Last Minute Discounts:

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.

Save 20% off the regular weekly rate through 4 April 2019 or 15% off 5 April 2019 through 15 November 2019. Applies to new reservations 6 nights or longer.
Offer Dates:
Now - 15 Nov 2019
Confirm before 18 Oct 2019
Foxy Lady will keep their calendar open for August 2019 sailing the Grenadines from Grenada with two crew and three dives included (max 2 dives in the Tobago Cays). Minimum charter 6 nights.
8 guests $29,800 7 nights
6 guests $28,800 7 nights
4 guests $27,800 7 nights
2 guests $26,800 7 nights
Offer Dates:
1 Aug 2019 - 31 Aug 2019
Confirm before 9 Aug 2019
Save $1,000 off new reservations aboard Oui Cherie with her talented crew. Discount can be prorated for 6 night charters.
Offer Dates:
Now - 17 Dec 2019
Confirm before 15 Nov 2019

Thank you for providing us with a fabulous vacation!

Colin and Julianna were tremendous and truly the best. The meals were like a 5 star restaurant. I told Julianna I truly believe she could beat Bobby Flay! We had a vegetarian and one that didn’t like spicy. Everyone was perfectly accommodated. 5 Stars. Colin was amazing also. I feel we were blessed to have such a great crew!

The yacht was perfect and we loved it all. Everything was perfect from booking until the end of the voyage. I will highly recommend you to anyone considering a wonderful vacation.

Earl H, aboard Catamaran Tabula Rasa, February 2019  sailing the Virgin Islands

Terry and Ruth were both amazing. They are delightfully friendly and good humored, exceptionally knowledgeable about all aspects of the charter experience, and very attentive to each guest. Ruth accommodated one couple’s special dietary needs superbly and without drawing attention to it.

The Big Dog was in excellent condition inside and out. The yacht was clean, neat, well-organized and very ship-shape. Very nice that the guest cabins are air conditioned. She sailed well and comfortably and is very well outfitted. We used the kayaks, paddle board and float numerous times.

Ruth is a master chef! Meal after meal she prepared and served outstanding cuisine, and Terry always found the perfect cocktails and wines to go with each. It was like going to a five star restaurant three times a day!

Great itinerary hitting all the destinations we sought. Terry is very knowledgeable about the islands, history, must-see sights and best anchorages, and he and Ruth have developed great contacts on each island for local transportation, shopping and restaurants.

Sailing Directions provided excellent and professional service and was easy to work with. The website was detailed, well organized and informative.

This charter far exceeded our high expectations. Terry and Ruth are outstanding professionals and we recommend them without reservation.

Eric S, aboard Catamaran The Big Dog, February 2019  sailing the British Virgin Islands

We had many choices of charter yachts to pick from and we feel we could not have made a better choice! From the moment we boarded, we felt welcome and the vibe was completely different from other charters we have been on. The yacht was spotless and welcome cocktails and snacks were awaiting.

The vessel was very comfortable, clean and obviously well maintained. The master cabin was huge! More than enough room with lots of storage. A water maker onboard is a big plus. There was plenty of ice for cold drinks and both crew were great bartenders!

Captain Taylor and Chef Margaret were both very professional. We noticed they both helped each other with daily duty’s and were always attentive to our needs, always putting us first!

Taylor was cautious when necessary and showed great seamanship. He gave me pointers on honing sailing techniques and mooring procedures. While diving, he was a great dive master, always being cautious and took us to new dive sites we never heard of before!

Margaret’s cuisine is amazing and always left us more than satisfied. Both went out of their way to accommodate us, with Margaret even taking us ashore on special tours of places we had not seen on other trips.

Overall, our experience was excellent, starting with timely correspondence with Sailing Directions, the yacht and crew. Taylor even arranged a driver to be waiting for us at the airport! When we return, we will look for the crew of the White House for our next adventure.

Sailing Directions is a well run company and I have already recommended them to a couple friends who are interested in chartering in the future.

Once again thank you for the attentive way you handled our trip. You made it very easy! We will be back!

Shawn R, aboard Catamaran White House, February 2019  sailing the Virgin Islands

> See all of our crewed yacht charter reviews

Caribbean Yacht Charter Vacations

A crewed Caribbean yacht charter offers you the freedom to explore this tropical paradise without limits and at your own pace.

With accommodation, a professional captain, a personal chef, all meals, cocktails, wine, beer, snacks, fuel, equipment, and water toys included, few other vacations offer such an extraordinary experience and value.

Itineraries are completely flexible within your cruising area. Sail the diverse US and British Virgin Islands, the undeveloped and resort islands of the Caribbean Grenadines, or charter a luxury power yacht to cruise St. Martin, St. Barts, and Antigua in the Caribbean Leeward Islands.

Sailing Direction's charter brokers help you book a private crewed yacht in the Caribbean for any group size and budget. Whether you're looking for a family sailing vacation, a couple's adventure holiday, a BVI yacht charter, or a honeymoon or anniversary celebration - we've got you covered for an unforgettable crewed yacht charter experience.