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 game fishing, world-class dive sites and sunshine every day of the year.

Sailing Directions® helps you find and reserve a crewed yacht charter in the Caribbean. We can find you a charter yacht that best fits your budget and needs; from an all inclusive family sailing vacation to a corporate group or an unforgettable honeymoon. 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 yacht charter broker with an extensive range of crewed yachts and a depth of expertise. Let the experts match you with the perfect crew and yacht for your needs. 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:

Fall 2014 and Spring 2015 Discount
Save up to $3,500 on 7 night charters occurring between 15th November and 15th December 2014, 1st and 31st January 2015 and 1st and 31st May 2015 sailing the British Virgin Islands aboard luxury crewed catamaran Soon Come.

Available for charters starting 15 November 2014 through 31 January 2015
Reservations need to be confirmed before 15 January 2015

10% discount for select dates in November, December and January

10% discount for any 6-night or longer charter sailing the Virgin Islands and taking place during the following dates:

8 November - 14 December 2014 and 6 - 31 January 2015

Available for charters starting 8 November 2014 through 31 January 2015
Reservations need to be confirmed before 12 December 2014

15% off available dates in November and December 2014 including Thanksgiving week
Save 15% on any new reservations booked for available dates in November and December 2014 sailing the Virgin Islands aboard Happy Time.

Available for charters starting now through 18 December 2014
Reservations need to be confirmed before 3 December 2014

These crewed catamaran specials are available for new charters sailing from Tortola or St Thomas in the Virgin Islands. 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


Catamaran Loveboat

, British Virgin Islands crewed Catamaran charter, July 2014

"We found the crew very very good, we had a great time with them and they helped us to enjoy it a lot, they were very friendly, attentive and accommodating. We had a very good relationship that continues nowadays via facebook.

Loveboat was comfortable, we felt at home. Linda is a very good cook and also Josh with his fantastic BBQ ribs. The meals were very tasty and well presented.

Captain Josh took us to wonderful places that we will never forget in our lives and he also taught us to sail, he is a very good teacher.

We had a great time and we will never forget of this trip, Josh and Linda and obviously the catamaran Loveboat that allowed us to have this fantastic sailing trip. "

Andres C, sailing the British Virgin Islands


Catamaran Yes Dear

, British Virgin Islands crewed Catamaran charter, July 2014

"Richard & Adele were incredible. Everything we could have ever hoped for. The food Adele was capable of preparing in a little boat kitchen was nothing short of amazing.

Yes Dear is excellent. The one small cabin was tight for the one couple staying in there but we knew that was going to be the case going in so no surprise there. The rest of the cabins were actually slightly larger than we thought they would be.

If we decide to return or hear of anyone else talking about it we will certainly recommend Sailing Directions and Yes Dear."

Brian W, sailing the British Virgin Islands


Catamaran Pentesilea II

, US Virgin Islands crewed Catamaran charter, July 2014

"We absolutely loved Andrew and Kailee. They were friendly, fun, and wonderful with our two teenage daughters. They were great and accommodating hosts!

The food was beautiful and delicious. Kailee should publish a cookbook!

We had such a wonderful time we are trying to figure out when we will be able to go again."

Stacey S, sailing the US Virgin Islands

> See all of our crewed yacht charter Reviews!

Yacht Charter Virgin Islands Leeward Islands Grenadines Ask Us - Caribbean Charters
Charter the Caribbean

Crewed yacht charter vacations in 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.

See crewed charter yachts available for your dates: