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:

15% discount for charters in 2015
15% discount off Zuma's rates for charters booked for 2015 sailing dates (excluding Xmas and New Years weeks) sailing the Virgin Islands or Caribbean Leeward Islands.

Available for charters starting now through 17 December 2015
Reservations need to be confirmed before 15 February 2015

10% discount available
Save 10% off Flying Ginny's regular rates for any reservations booked between now and 31 January 2015 for charters sailing by the end of 2015 (Christmas and New Years weeks excluded)

Available for charters starting now through 15 December 2015
Reservations need to be confirmed before 31 January 2015

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 now through 31 January 2015
Reservations need to be confirmed before 15 January 2015

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 Best Revenge 5

, British Virgin Islands crewed Catamaran charter, December 2014

"Nick and Lucy are top notch professionals. They are very friendly, engaging, and very accommodating. Nick was an excellent captain who is a competent sailor, very knowledgeable about boating and maintenance, marine life, local history and folklore. He escorted us in the water and on land, always looking out for our safety.

Best Revenge 5 is a beautiful, well maintained and very clean vessel. There was plenty of hot water on board and AC worked well with individual thermostats in each stateroom. Bed linens were also nice.

Food on board was fabulous. Although not formally trained as a chef, Lucy's culinary skills were off the chart. Her passion for cooking was evident in menu selection, food preparation and presentation, and all the care she took to accommodate our food preferences. She prepared three fabulous meals each day, and varied the menu throughout the week. Her cooking skills and desire to please the guests make her a true asset.

With constant consideration of prevailing winds and sea conditions, Nick planned out an excellent itinerary and offered us options all along the way.

Sailing Directions was always quick to reply to emails and answered all of my questions in a timely manner.

Our gal pal charter aboard BR5 in the BVI far exceeded our expectations."

Susan V, sailing the British Virgin Islands


Catamaran Flying Ginny

, British Virgin Islands crewed Catamaran charter, November 2014

"Peter and Caroline were extremely friendly. Both were very attentive to us and the 6 teenagers that we bought with us. Both had patience of a saint when it came to the 3 teenage boys and 3 teenage girls.

The boat was clean and very comfortable, plenty of room for 8 people and crew.

Food was excellent and nicely presented. We had some kids that were afraid to try new foods however Caroline was very accommodating in making different meals for those that were more "picky".

The itinerary was great. We hit the main spots and even got to take in some new spots we have never been too. Peter put the safety of his passengers and crew in mind when we planned each day.

We would definitely recommend Sailing Directions to any friends that may consider a sailing vacation."

Kelli D, sailing the British Virgin Islands


Catamaran Frangines

, US Virgin Islands crewed Catamaran charter, November 2014

"Thank you! This was a fantastic time in every way. The food was just perfect. We didn't have Captain and First Mate, but new and endearing friends. THANKS!!

On a scale of 1-10... 15! Capt. Will and Nikki made a perfect team and gave us the time of our lives.

This trip was AMAZING!! The boat was phenomenal. Comfortable. Fun. Spacious for our dance party. Nikki and Will took care of us like no other. The beaches and cays we stopped at were heavenly, and the food NIkki made was over the edge. We could not have asked for a better or more fun trip. Thank you a million times.

This trip was perfect in every way! Every view was a postcard. The wind, the water, & the rain, my favorite spot was the chairs in front on the bow riding the waves, or just relaxing in the hammock. I couldn't have asked for more. Will and Nikki took care of us beyond expectations. The food was amazing! It was delicious and perfectly timed! We awoke every day to fresh brewed ice tea, our belongings lovingly folded- what can I say- pure bliss! "

Tim M, 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: