Crewed Caribbean Yacht Charters

Start here: Search for Available Crewed Charter Yachts

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:

> See all Specials and Discounts

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

10% Discount for Bahamas charters in August, September & October 2015
Save 10% on Something Wonderful's rates sailing the Bahamas this summer and early fall, August through October.

Available for charters starting 1 August 2015 through 30 October 2016
Reservations need to be confirmed before 19 September 2015

5% discount in May 2015
Save 5% on crewed charters sailing in May 2015 sailing the Virgin Islands aboard Miss Kirsty.

Available for charters starting 1 May 2015 through 31 May 2015
Reservations need to be confirmed before 10 May 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.

> See all of the current crewed yacht charter Specials and Discounts!

Latest crewed yacht charter Reviews

> See all of our crewed yacht charter Reviews

"In a word, our experience was exceptional. The Vessel, Lady Alliaura, was in absolutely first-class condition, providing an abundance of space for our party of eight and crew of four. The air-conditioning, particularly for the staterooms, made the nights very comfortable. The layout of the afterdeck where we dined and spent most of our time under sail and the visibility and layout of the upper deck, salon, and staterooms exceeded all of our party’s expectations.

The Crew were engaging, pleasant and focused on providing each guest with a unique and remarkable experience. The Captain, Sebastian Leclerc, was a deliberate, accomplished and composed seaman with strong leadership skills. The mate, Caroline, was an accomplished sailor with a good sense of humor. The chef, Laurent, possessed an unusually good humor since he spent most of his time in the galley preparing meals fit for a king. The hostess, Celine, was intuitive, gracious and very attentive to everyone in our party.

The Experience overall was exceptional to any of my prior chartering efforts. The legs of our itinerary were well laid out with thoughtful consideration for the comfort of our party as it related to selection of anchorages, sails and time on the open water, the high point of which was a gorgeous night sail from Barbuda to the eastern side of St. Maarten.

Our entire party of eight, without exception, thoroughly enjoyed our adventure and will certainly look forward to another opportunity to sail on Lady Alliaura with her exceptional crew at some future date.

And to you, John, a tip of the hat for the professionalism and assistance you provided me in organizing and preparing for each member of our party’s comfort, menu preferences and special meal requests, recommendations on packing, and arrival/departure from Lady Alliaura. I’m appreciative of your efforts on our behalf. For years to come, each member of our party will fondly remember the crew, the vessel and our time aboard Lady Alliaura."

, aboard Catamaran Lady Alliaura, April 2015 sailing the Caribbean Leeward Islands

"The Crew on Steppin' Up are amazing - they go above and beyond every step of the way. We cannot say enough good things about them. They are friendly, attentive and accommodating! From the minute we arrived when they were waiting in the parking lot for us, had a wonderful lunch already prepared, to the very end when they took us back to town before having to catch our flight. We felt completely spoiled and confident in Bill and Michelle.

Bill is a calm, cool, collected and very knowledgeable captain - but with a fun sense of humor and easy going/relaxed spirit. Michelle is not only a fabulous chef, but always made sure everything was always so clean, tidy, picked up and you didn't even realize they were doing it. They looked out for us - our safety and enjoyment. They were so easy to get along with and feel instantly comfortable with - we lucked out!!

The boat was very comfortable, clean and well ventilated. It was also well equipped from big toys to little things like games and extra supplies.

The food was delicious! All of it made from scratch and wholesome. Michelle always had a snack ready, fresh fruit, wonderful meals, always offering something to drink. Everything was with a smile and she never showed any stress or effort - it all just magically happened. She was very accommodating with our son who has a gluten and dairy intolerance. Michelle is a pro and always has a smile on her face, a kind word and a helpful attitude. I will be trying to copy many of her dishes for a long time to come!

The itinerary was spot on to what we expected and actually exceeded our expectations. They seemed to have a knack at finding the quieter space or the best mooring or the perfect snorkeling or swimming hole. We were very pleased at our destinations and appreciated them listening to things we really wanted and working the schedule to fit in with our requests. Bill is really a captain to trust and again was so knowledgeable about the islands was a very gracious host.

Abundant comfortable lounging areas - in the bow, the trampolines have nice cushy head pillows, there are 2 comfy lounge mats and then 2 benches and a seat that are also fitted with very comfortable and attractive cushions. The cockpit and cabins are also very welcoming and comfortable.

We loved that they were at this lovely marina that was so easy to get to/access and welcoming. It made the whole transition on and off the boat much easier!

Bill and Michelle go above and beyond making sure each one in our family gets to do what they love to the most. They also had fun things for our boys ready for them - little basketball hoops for their cabins, treasure chests full of candy, etc. They were just a joy to be with and it was easy and fun - a trip of a lifetime!

Sailing Directions was great to deal with and the process was very smooth. Thank you for everything."

, aboard Catamaran Steppin Up, April 2015 sailing the US Virgin Islands

"Stephen and Julia were wonderful. They took care of our every need. They accommodated every request. They were most friendly and a real joy.

The food was unbelievably delicious and visually fantastic. The itinerary was perfect. Safari was absolutely comfortable. "

, aboard Catamaran Safari, April 2015 sailing the US Virgin Islands

> See all of our crewed yacht charter Reviews!

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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: