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!
1 child age 6 years or younger sails free
1 child age 6 years or younger sails for free aboard Lagoon 450 catamaran Gypsy Princess. Limit 1 free child per charter. Sailing the Virgin Islands.
Available for charters starting now through 31 January 2016
Reservations need to be confirmed before 31 January 2016
15% discount through November 2015
Save 15% on Lady Katlo's charter rate for any reservations taking place between now and 5 November 2015. Lady Katlo is available in the BVIs through late May and sailing in the Grenadines from mid June.
Available for charters starting now through 5 November 2015
Reservations need to be confirmed before 1 October 2015
Currently available for Christmas and New Years weeks
Charter the stunning Damrak II for Christmas or New Years week in the Caribbean with up to 8 passengers @ $39,000 + 10% holiday premium.
Available for charters starting 18 December 2015 through 9 January 2016
Reservations need to be confirmed before 19 September 2015
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.
It was a fabulous vacation. We will definitely do this again!
Andre and Liezl were so awesome. “No” was not in their vocabulary. Leizl was fun, enjoyed interacting and playing games with us as well as preparing the most fantastic food! Andre was so energetic, he was a great dive master, and was always making sure we were entertained whether it be taking someone to the island by dinghy or by taking the kids out tubing, kneeboarding or wakeboarding. He even got me up on the wake board. Their recommendations of where to go for nightlife for the kids or eating ashore were wonderful.
Yes Dear was very clean and the staterooms were very comfortable. We loved hanging out in the front, in fact one of the kids slept out in the front every night. I think every loved to gather around the table in the rear and play games and just laugh.
The food was out of this world. I was concerned we might have some picky eaters but she made food enjoyable to adults and kids.
The itinerary was so wonderful. Our only regret was not having more days to enjoy more of this.
Sailing Directions was always on top of things. The website was good about recommendations for water taxis and the cost of things.
This is such a first rate vacation. We never felt cramped on the boat and everyone had their space. The boat Yes Dear had some great games and movies and we also brought some of our own. This will be a memory for a lifetime.
Jennifer G, aboard Catamaran Yes Dear, July 2015 sailing the British Virgin Islands
Bryan and Ava were great with a nice mixture of being attentive when necessary and providing privacy other times. They were very knowledgeable and our group was constantly asking challenging questions which they answered very well. Bryan and Ava are a wonderful complimentary team!
Happy Time was very comfortable and well ventilated. A/C worked well in cabins. Favorite aspect was the spacious back-deck eating area. We played many games, drank, and dined well in that locale.
Food and variety of menu was excellent for all meals. We had a tree nut allergy amongst the party and they dealt with that perfectly. Bryan is an excellent grill master and we had several meals that were grilled to perfection (tuna steaks stand out)!
We worked closely with the crew to develop an itinerary and each day we went over options based on different preferences in our party. Worked great!
Sailing Directions is always our first stop when looking at chartered yacht vacations. We have always had good service and specifically John Lane’s communications and support is top notch! I am frequently giving Sailing Directions contact information out to anyone expressing interest.
Kirk N, aboard Catamaran Happy Time, July 2015 sailing the US Virgin Islands
The crew were absolutely excellent in every single aspect of the trip! Rich and Lisa’s commitment to our enjoyment, experience and safety was awesome. Nothing was too much trouble; they gave us a 5 star experience of the highest standard, from the moment we arrived to the second that we left.
Zingara was in fantastic condition. Spotlessly clean and equipped to the highest standard and extremely comfortable. Our favorite aspect was hanging out on the top deck during afternoon sails and again with after dinner drinks.
The quality of the food and variance of the menu, was the biggest single surprise of the trip. We are a well-travelled group and the food was among the best we have ever had! Rich is truly an excellent chef, wonderfully supported by Lisa. The cuisine was amazing!
Could not have asked for more from the BVIs - stunning!
We would use you guys again without hesitation and Rich and Lisa would be our absolute preference to stay with again. They made the trip!
As you can tell from our comments we were hoping for the trip of a life time to celebrate my wife Dee’s 50th birthday and the trip exceeded every single expectation we had! Our group has literally travelled the world and the consensus of opinion was this was the best trip any of us had ever done. We will remember the trip for a very long time.
John M, aboard Catamaran Zingara, June 2015 sailing the British Virgin Islands
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.