Experience the vacation of a lifetime aboard a luxury, all-inclusive, professionally crewed catamaran, sailing or power charter yacht in the Caribbean.

Escape to white sandy beaches, consistent Caribbean trade winds, clear blue water, customized gourmet dining and fresh cocktails, sheltered islands grouped close enough for great day sailing, world-class dive sites, award winning yachts and crew, and sunshine every day of the year.

Sailing Directions® helps you book a crewed yacht charter in the Caribbean Virgin Islands, Leeward Islands and Grenadines. We will match you with a charter yacht that best fits your budget and needs; from an all-inclusive family or couples sailing vacation to a corporate incentive party or an unforgettable honeymoon or anniversary charter. We make the booking process easy via our website and experienced charter brokers, provide a wealth of information and support to help you prepare for your trip and get the most out of your yachting vacation.

Sailing Directions is an independent crewed yacht charter brokerage which has been in business since 2005 with access to an extensive range of crewed yachts. When you book a private crewed yacht through us you get peace of mind that our advice is unbiased and your payments are held in a secure 3rd-party escrow account until the charter date. We also accept credit card payments through our secure website.

We specialize in crewed catamaran charter vacations sailing the Caribbean Virgin Islands. We have firsthand knowledge of the boats and crews and have broad knowledge of the Virgin Island cruising areas.

Find your ideal crewed yacht using our live online availability search form now or contact us to start planning your unforgettable Caribbean crewed yacht charter vacation!

Specials and Last Minute Discounts:

> See all specials and discounts
Lir
Lir is offering 2018 discounts of 15% off for 7 night charters between the following dates:
16th August - 28th August 2018 in the Windwards/Grenadines and
20th October - 14th December 2018 in the Grenadines or Virgin Islands
Offer Dates:
Now - 14 Dec 2018
Confirm before 16 Nov 2018
Save 10% off new 7-night reservations sailing in 2018. Special excludes Christmas and New Years dates.
Offer Dates:
Now - 15 Dec 2018
Confirm before 1 Nov 2018
Save 10% off new 7-night reservations sailing in 2018. Special excludes Christmas and New Years dates.
Offer Dates:
Now - 15 Dec 2018
Confirm before 1 Nov 2018

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

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

Conor & Taylor are very comfortable to be around. Connor was always asking how we were doing and if we needed anything - we loved his happy hour drinks!

Great Adventure has a great outside layout and cabins (each with its own shower and controlled thermostat).

Food was Amazing! Beautifully presented and perfect portions. Taylor is an amazing cook. We looked forward to apps and meals every day and were not disappointed.

Tom G, aboard Catamaran Great Adventure, July 2018  sailing the 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 and monohull sailboats 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.