Book an unforgettable crewed yacht charter vacation.

View Available Yachts:

Book with the Caribbean specialists. For over 14 years 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 $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
Mojo is offering 15% off their rates new reservation taking place during the months of April & May 2019. 6 night minimum charter applies.
Offer Dates:
1 Apr 2019 - 31 May 2019
Confirm before 28 Feb 2019 Expires in 37 Days
Save $1,500 on the 7 night rate on charters through April 2019. Applies to the next 5 charters booked.
Offer Dates:
Now - 30 Apr 2019
Confirm before 9 Apr 2019

The cruise aboard Lady J was great. The kids and grandkids loved the trip and the crew, and I think the crew loved the kids. Happy New Year!

Heather H, aboard Power Yacht Lady J, January 2019  sailing the Bahamas

Simply amazing! Both Rich and Lisa provided outstanding service. They were both very knowledgeable and very accommodating. We couldn't have asked for a better crew!

The Luar was very comfortable and immaculate. Lisa was always cleaning! I loved the sundeck up top to watch the stars!

Oh my gosh, the food was amazing! Rich and Lisa accommodated teenagers and my allergies. My teens came home raving about the food.

Rich was super smart and with it being New Year's week - he reversed the itinerary after hearing me comment I'd prefer not to be with lots of boats. On average we moored with 2 other boats - perfect!

The crew makes a boat / week.

Mary Ann S, aboard Catamaran Luar, January 2019  sailing the Virgin Islands

The crew were phenomenal! We listed some “want to see” locations but we trusted them to know the area and take us to special spots and they did just that!

The food was gourmet level at many meals and beautifully presented. We especially loved the shaded lounge area at the stern.

Barbara H, aboard Catamaran Free Ingwe, December 2018  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.