Book an unforgettable crewed yacht charter vacation.

View Available Yachts:

Book with the Caribbean specialists. For over 14 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 all summer bookings aboard Luna sailing the Virgin Islands and Grenadines. Four night minimum charter.
Offer Dates:
Now - 31 Aug 2019
Confirm before 16 Aug 2019
Santa Ana is offering 20% off new reservations for available dates sailing in June or July 2019 sailing the Virgin Islands. 5 night minimum, discount may not be combined with any other special.
Offer Dates:
Now - 19 Jul 2019
Confirm before 3 Jul 2019 Expires in 14 Days
Save 15% off new reservations sailing now through 15 November 2019. Applies to new reservations 6 nights or longer.
Offer Dates:
Now - 15 Nov 2019
Confirm before 18 Oct 2019

A huge thank you for your assistance in booking this past week's charter vacation aboard the Xenia74.

We were four couples in celebrating important wedding anniversaries and wanted the best. The Xenia74 boat, accommodations, crew, meal service and sailing experiences exceeded all expectations as we sailed among the British Virgin Islands.

The Xenia74 has a magnificent master bedroom and three other bedrooms all with top notch out fittings and superb air conditioning.

Captain Tony with 20 years of experience provided smooth sailing and excellent access to snorkeling, scuba and beach combing.

Chef Kate in our unanimous opinion is the BEST in the Caribbean. From elegant omelets and freshly made croissants in the morning to wonderful salads for lunch and perfectly cooked to our preferences fish, chicken, lamb chops and steak at dinner we were blown away by her preparations. Did we mention the fluffy pancakes, the decedent French Toast or what she does with balsamic glacé? Desserts were also superb. Her chocolate raspberry cake has to be the best in the Western Hemisphere.

We brought along a case of our favorite wines which were amply fill out by Xenia74’s inventory of American and French wines. There is an extensive variety and supply of various liquors on board too.

The yacht’s two additional crew members Katie and Nick provided superb support and added tremendously to our wonderful experience.

This was a marvelous once in a lifetime trip made perfect by this handsome boat and superb crew. Booking on any lesser boat would be a shame and missed opportunity for perfection.

We should have booked two weeks!

David B, aboard Catamaran Xenia 74, June 2019  sailing the Virgin Islands

We had an amazing trip! Richard & Dominique were absolutely perfect. Richard helped us create an itinerary that was perfect for our family. Dominque was a sweetheart with our girls and an amazing chef. We enjoyed getting to know them.

Mojo was always clean. The beds were super comfortable. We loved the walk through at the front of the boat. We spent a lot of time on the trampoline and the sitting area up front.

Dominique adjusted portion sizes as needed for my growing teenagers and younger girls. Everything was absolutely delicious. We looked forward to each and every meal.

You website is wonderful and your quick replies to my initial questions was the main reason we went with Sailing Directions. This will not be our last charter. We will definitely be back and would recommend you to friends and family.

Sandi S, aboard Catamaran Mojo, June 2019  sailing the Virgin Islands

Our charter trip on Excess with Ben & Michelle was amazing. I don't think I could have made a better choice on a catamaran selection! The boat was spotless and well ventilated and air conditioned. From the moment we stepped on Excess to the time we left, Ben & Michelle were awesome.

We called Ben the "Indiana Jones" of the ocean! He was up for anything from taking us snorkeling, scuba diving, hiking and exploring to finding a beautiful, quiet cove to just kick back and relax, swim and read. My son caught live lobster on his dives with Ben and he prepared them fresh on the boat for us!

Michelle's cooking was exemplary. Fresh, beautifully presented and healthy!

Ben & Michelle are such easy going, fun and down to earth people which made it so easy for our family to settle right in and relax. They made it fun and adventurous for our 4 children ages 16-23.

Excess is a beautiful catamaran with a spacious master suite and plenty of room for our family of 6 to spread out and enjoy some alone time.

The quality family time that we experienced was the best part of our week. Hands down, our best family vacation ever with the most beautiful catamaran and the greatest crew in the Caribbean!

Toni H, aboard Catamaran Excess, June 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.