Availability Search

It is time to experience the vacation of a lifetime aboard a luxury, all-inclusive, professionally crewed catamaran, sailing or power charter yacht in the Caribbean.

Escape from the icy winter to white sandy beaches, consistently light Caribbean trade winds, clear blue water, gourmet dining and fresh cocktails, islands close enough for day sailing, outstanding offshore game fishing, world-class dive sites, award winning yachts and crew, and sunshine every day of the year.

Sailing Directions® helps you find and reserve a crewed yacht charter in the Caribbean Virgin Islands, Leeward Islands and Grenadines. We can find you a charter yacht that best fits your budget and needs; from an all-inclusive family or couples group sailing vacation to a corporate party or an unforgettable honeymoon or anniversary charter. We provide a wealth of information and support throughout!

When you book a private crewed yacht through us you get all of our services as well as peace of mind that our advice is unbiased and your payments are held in a secure 3rd-party escrow account until the charter date.

Sailing Directions® is an independent crewed yacht charter brokerage with an extensive range of crewed yachts and a depth of expertise. We specialize in crewed catamaran charter vacations sailing the Virgin Islands. Let the experts match you with the perfect crew and yacht for your needs and price point. We know all of the boats and have extensive knowledge of the local cruising areas. Start your search now using our live online availability search form or contact us now for your unforgettable Caribbean crewed yacht charter vacation!

Specials and last minute Discounts:

> See all Specials and Discounts
Details:
$2,500 per week discount for any new charter sailing in 2017. Discount does not include one appetizer and dinner (you'd dine ashore for this).
Dates:
Available for charters starting now through 15 December 2017
Reservations need to be confirmed before 1 November 2017
Details:
15% off any new reservations taking place from now until 30 June 2017 sailing the Caribbean Grenadines, Leeward Islands or Virgin Islands. Valid for new bookings only, 5 night charters or longer.
Dates:
Available for charters starting now through 30 June 2017
Reservations need to be confirmed before 2 June 2017
Expires in 35 Days
Details:

5% Earlybird discount off the listed rates for charters sailing between 1 December 2017 and 1 August 2018 - that 's right, a year from now - Book early and SAVE!

Does not include holiday weeks.

Dates:
Available for charters starting 1 December 2017 through 1 August 2018
Reservations need to be confirmed before 29 April 2017
Expires in 1 Days

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

We had such an amazing trip. The boat is beautiful, and John and Shirelle were the most wonderful hosts. They made our trip fun, were knowledgeable and easy going about where we should go and what to do each day. Shirelle is such a talented cook. They were very flexible and helpful when deciding our route and always made sure we were well fed!

The yacht was beautiful. Very airy and well stocked with everything we needed. We loved the back seating area and upper deck seating areas.

The food was absolutely delicious. There was plenty of it, a wide variety each day and Shirelle was great with dietary requests.

Given this was our fifth charter we were pleased to try some new areas and snorkel spots. Everything was really great. We had a wonderful time.

David F, aboard Catamaran Amazing Blues, April 2017 sailing the British Virgin Islands

Matt & Tara couldn’t have been more friendly and welcoming!

Nana was a great boat, very comfortable for our group. Outdoor space was the best part of the boat.

The food was fantastic. Presentation was superb. Preferences were well customized, thanks Tara!

We tweaked the itinerary as we went along and found the best snorkeling and places to stay.

Sailing Directions were very organized and great to deal with. Information on the website was great. We would certainly recommend your services to others.

Nina H, aboard Catamaran Nana, April 2017 sailing the British Virgin Islands

What a fabulous week! We could not have asked for two more experienced and knowledgeable pairs of hands to charter us through the British Virgin Islands. And what a comfortable and well-appointed boat to do it in - we had no idea our accommodations would be so luxurious!

We loved all the quiet anchorages off the beaten track that you took us to. We all enjoyed boating and swimming off the boat. The kids learned to snorkel and to kayak and are quite pleased they all got to drive the dinghy. And as we said every day, the food was amazing! The meals far surpassed our expectations and were graciously served every time. The kids told us that we need to "bump it up" when we get home!

My husband had been talking about sailing in the BVI for some 25+ years and we will now have our own memories of crystal blue waters, white sand beaches, sunny skies and wind in our faces as we sail across the waters.

Thank you for helping to make this a wonderful and memorable experience for our family.

Chantal K, aboard Sailing Yacht Pacific Wave, April 2017 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, monohulls and catamarans 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.