Book an unforgettable yacht charter vacation.

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Established in 2005, our independent yacht charter brokerage helps you discover the tropical Caribbean aboard exceptional private crewed charter yachts. Working with our experienced charter brokers is easy and their firsthand information about the available yachts and crews helps you choose the best option for your group. Start planning your vacation today with the crewed Caribbean yacht charter specialists.

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

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.
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crewed sailboat charter

Monohulls

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.
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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.
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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.

$1,000 off any charter booked and completed by 12/18/18. Applies to full-board, half-board and local fare. May be prorated for 6 nights.
Offer Dates:
Now - 18 Dec 2018
Confirm before 9 Dec 2018
Book 7 nights between November 17th and 25th and only pay the 6 night rate.
Offer Dates:
17 Nov 2018 - 25 Nov 2018
Confirm before 31 Oct 2018 Expires in 14 Days
Seahome is offering a complimentary Lobster dinner in Anegada or Foxy's for Thanksgiving week 2018.
Offer Dates:
17 Nov 2018 - 25 Nov 2018
Confirm before 31 Oct 2018 Expires in 14 Days

Our customers say it best. Check out their feedback.

Tyler & Kelsey were awesome.

Re Playtime: We loved it all. Like the convenience of having an icemaker and water maker. We enjoyed the upper deck lounge area as well.

The food was wonderful, tasty, and customized to dietary preferences. It was always beautifully presented.

We enjoyed everywhere we went. Kelsey was like our personal tour guide offering stories, fun, historic & scientific facts.

Thank you!

Jamie H, aboard Catamaran Playtime, July 2018  sailing the Virgin Islands

Theunis & Rebecca were friendly, knowledgeable, attentive and accommodating. Great crew.

We love the king size beds aboard Anastasia. Theunis is a wealth of information. Rebecca is a great chef. Could not have had better food anywhere.

John at Sailing Directions was a great help in planning this trip. He always answered my emails in a timely and helpful manner.

Priscilla F, aboard Catamaran Anastasia, July 2018  sailing the Virgin Islands

This vacation was outstanding. It ranks in my top 3 trips of all time. Thanks for helping us book the adventure and ensuring our success.

Graham and Kristiann were as good as it gets. Their attention to detail, knowledge of the area and sailing, plus constant focus on our safety and entertainment made this vacation spectacular.

Allende was extremely comfortable, clean and well ventilated. While I have very limited sailing experience, I do have extensive inland water boating experience. The layout of Allende was extremely comfortable. I never felt confined or cramped.

My favorite aspect of the yacht becomes difficult to answer, because it really depended on the time of day. In the mornings, I found it extremely relaxing to be up top on the sun pad to stretch and enjoy a cappuccino (they had a professional cappuccino machine - I mean come-on!). In the evenings, the outdoor aft lounge was perfect to relax with a drink and watch the sunset. Plus on several nights, they used a green egg grill to cook dinner. So it does not get much better than watching a Caribbean sunset while smelling a grill cooking up dinner. And lastly, sleeping; the cabins can be turned down to a low temp while the gentle rocking puts you to sleep. I had some of the best sleeping that I can remember while onboard Allende. So my favorite aspect of the yacht is difficult to choose.

The menu was certainly customized to our preferences. Kristiann even made separate meals a few times when she knew one of our guests would not enjoy the dish everyone else was eating. The food was extremely well prepared and almost all of it was prepared from scratch. It was the quality of high end restaurant. Very impressed!

The itinerary was just what we were seeking. Each night we discussed the next day’s route and agenda. And if desired, we could change things up to do more or less of an activity.

I am extremely happy with Sailing Directions. John was certain to be sure our desires and budget matched perfectly with the yacht and crew. Sailing Directions' website made my selection much easier.

I must say that vacations usually take about three days for me to finally relax and enjoy the trip. This vacation on the Allende with Graham and Kristiann was different. I was completely relaxed by the first morning. It was perfect!

David K, aboard Catamaran Allende, July 2018  sailing the British 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 at your own pace. Choose your itinerary, activities, and personalized food and drink menu unlike any cruise ship, resort, or beach side hotel.

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, or a honeymoon or anniversary celebration - we've got you covered for an unforgettable crewed yacht charter experience.