Crewed Caribbean Yacht Charters

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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:

10% Discount for charters confirmed by 15 March 2015
Save 10% on Something Wonderful's rates in 2015 for reservations confirmed by 15 March 2015 sailing the British Virgin Islands.

Available for charters starting now through 16 December 2015
Reservations need to be confirmed before 15 March 2015

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

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 Gypsy Princess

, US Virgin Islands crewed Catamaran charter, January 2015

"The entire trip was a complete success. Shane and Anne were truly professional and made our vacation quite special."

Michael M, sailing the US Virgin Islands


Catamaran Genesis

, Caribbean Grenadines crewed Catamaran charter, January 2015

"Petr and Tracy were extremely accommodating and attentive. Tracy is a very talented, delightful, warm and friendly Hostess% Chef. Petr is a masterful, skilled, safety conscious Captain who went out of his way to make some very "sporty" (his word) sailing conditions as comfortable as possible for us. He did his best to find anchorages that were as smooth as possible given the sea conditions. He was extremely attentive, helpful with sound advice on snorkeling technique, loaned us his own snorkeling equipment after ours proved inefficient and was diligent in keeping a close eye on us while we were snorkeling or swimming. Petr was extremely skilled at maneuvering the catamaran in challenging conditions and these skills enabled us to land two sailfishes, two large barracuda as well as a black-fin tuna while under sail. Tracy and Petr were both also great help, and great fun in encouraging us and helping us land (and release some) of the results of our fishing efforts both under sail and at anchor.

Genesis was immaculate on our boarding her and Tracy and Petr made sure that she was maintained this way for our entire 10 day sail. Our quarters were spacious, beautifully clean, airy and the fans provided, as well as the cross-breeze from the windows in the sleeping area and in the bathroom, created very comfortable sleeping conditions. There was plenty of storage and Tracy ensured that our sleeping area and bathroom were beautifully maintained throughout our sail. There were vases of exotic, locally grown, fresh flowers and foliage in our cabin and in the salon and Tracy's innovative and lovely shell night-lights made getting around our quarters during the night very comfortable.

The food was delicious, beautifully and artistically presented. Tracy's creative flare was evident in the presentation of every single dish of each meal, including (within a few minutes of our impromptu request) a beautifully arranged and presented cheese-board which we had one day instead of lunch. The meals were generous and varied. The flavors, colors and textures were eye-catching, appetizing, fresh and bright. The dishes that Tracy prepared for us (per our request) were a mix of familiar North American-style fare and dishes representative of local cuisine. Tracy and Petr made excellent use of local ingredients, fruits, vegetable, herbs and fish and as a bonus, made good use of some of the products of our fishing luck. Petr treated us, one evening to Bramboracky, a Szech dish. It was a great treat, not only because it was delicious but because we were impressed by the versatility of his skills! (He is also a skilled barbecue chef, grilling many of the protein components of our meals on the small barbecue off the back of Genesis.) Tracy and Petr's gorgeous collection of batik napkins and sea-themed, napkin -rings (Never repeated once- during our 10 days of sailing!) were a visual delight, making the table a feast for the eyes even before the food was served.

We enjoyed the itinerary and areas sailed in the Grenadines. Unfortunately the weather disallowed some of the beach time and snorkeling that we would have loved to do, but this is a good excuse for us to sail this itinerary on the Genesis with Petr and Tracy again, in hopes of better weather from Mother Nature.

Sailing Direction's service was excellent. We appreciated the prompt, efficient replies to all our queries and to the pre-and post- sail communications. We loved having access to our sailing details on the Sailing Directions web-site as well as the preparation info section.

We will gladly and unreservedly refer anyone who expresses interest in a sailing trip."

Rejanne K, sailing the Caribbean Grenadines


Catamaran Blue Moon

, British Virgin Islands crewed Catamaran charter, January 2015

"The vessel is truly sailing and sleeping in total comfort and style. There are areas available on the fly bridge, salon, up front near the trampoline areas in the cockpit, as well as he back deck seating for couples to have privacy and some space in addition to each of the very comfortable cabins.

The linens are top notch and the d├ęcor is so perfectly blended with the vibe in the BVI. The toilets are electric so no "pumping" to flush as most people have experienced on some boats. Blue Moon has plenty of toys and recreational equipment with a kayak, paddle board, rafts, noodles and a six person float with drink holders. The dinghy can be used to pull you behind it with a kneeboard, etc too. Snorkel gear is available and if you wish to dive or fish, they will coordinate that for you as well. There is one hair dryer on board (though you'll rarely if ever use it), and there are stocked shower gels, shampoo, and conditioner dispensers in every shower, and at the back of the boat at the top of the sugar scoop so you don't need to pack those supplies unless you choose to. I found them to be great products and smelled very nice.

The boat has wifi and satellite TV (though we only bothered to turn it on once during our trip, for the bowl games on Jan 1st). Beach towels are provided and you do not need to pack them. They stow your suitcase%luggage for you so it's not in the way and you live out of the more than ample storage space and drawers in your cabin. No one could fill all the drawer space in the spacious quarters for a one or two week trip.

Packing advice: You'll read lots of things that say pack light, but I'm telling you I travel a lot for business and pleasure and rarely over or under pack. I kept this in mind and still over packed! When I go back next year, I'm taking swimsuits, maybe 3 shorts%t-shirts%outfits and 3 beach covers plus my toiletries. Unless you are doing upscale dining at a luxury resort ashore at night, you will rarely wear clothes beyond your swimwear and the t-shirts etc. that you'll buy along the adventure.

The tours, islands, and the overall options available throughout the BVI are endless. Captain Jack and Jaimey will accommodate any place you wish to go or see, and no two tours are really ever the same. Spots I would recommend you not miss are Bitter End Yacht Club, Soggy Dollar, The Baths, and a ride ashore around Virgin Gorda. Certainly there are plenty of other choices, but these are all must see%do items on every first timers list to say the least. We also enjoyed the Marina on the side of JVD where Foxy's Taboo is. Very nice stop whether or not the bubbly pools are active that day or not. They often find just the perfect spot, bay, or cove to anchor for a delightful breakfast with a fabulous view which may include caves (you can later snorkel) or a beach you can swim to. Captain Jack will dingy you to shore for tours, to reefs for a snorkel, or to a dock for nightlife. He absolutely does not mind picking you up, no matter how late it gets. He really is the best and you feel no imposition at all.

Jaimey and Captain Jack are absolutely unparalleled hosts. They think of everything, and make you feel completely at ease. We had coordinated and emailed several times before the trip and spoken to Captain Jack once to firm up details about 3 weeks prior to our trip, and literally from the moment we arrived, we did not feel like guests at all. They showed us all around, and made sure we knew where things were and how to use them. They had snacks and drinks waiting, and options for us to choose from that first afternoon. By the time dinner was over that night we felt like they were on the vacation with us and we'd known them for a long time.

They do the "beds and heads" so discretely each day before you even realize they were ever missing. (They've already made your bed and cleaned your cabin.) Captain Jack is a wealth of information about the islands and historical details about the BVI. Each morning after breakfast he gets the map out, reviews where you've been and what that day's options are, and then the group lets him know their preference for the day's sail and destinations. He's happy to involve you in the sailing activities if you wish to, or you can just relax and watch.

Jaimey doubles as the 1st mate and chef, and while it's hard to tell which one she's best at, you'll truly be "wowed" by her galley skills. She doesn't miss a thing on your preference sheet, accommodates different diet types with ease, and prepares and presents each meal in a way that is simply out of this world. We actually ate ashore one evening, and while it was good, we all wished we'd stayed aboard Blue Moon for Jaimey's dInner!

Captain Jack sets the table each day with fresh beautiful linens, followed by Jaimey describing that meal's offering as it is served. Her dishes stimulate one taste bud after another as well as plated with stunning presentations and garnishes. Truly each meal was better than the next, and just as we thought she couldn't possibly top one - she would! They are so Kodak-moment-like that you almost think they are too pretty to eat. (We always took a picture first though!) You are served breakfast, lunch, afternoon snack tray with happy hour, followed by dinner and dessert. Fresh baked cookies are made many days as well. She makes many of the breads herself and has become a master of local fresh provisioning. We had a pirate themed party one night complete with costumes. They pulled together costuming and joined us. Jaimey made a pirate themed dessert that night with cupcakes and decorations and pirate inspired drinks for us too.

I really cannot say enough good things about Jack and Jaimey. We felt like family and were just as sad to leave them, personally as we were to leave the beautiful island destinations they showed us. They are game for anything, think of everything, have endless tips and recommendations, unmatched service and are the kindest and fun people we could have ever hoped would crew our vacation sail and become "part of the family."

There is absolutely no doubt we will be back, and the only choice for us is Blue Moon with Captain Jack and Jaimey. My only worry is that as word about them continues to travel, they may be already booked the week we decide to go!

I cannot imagine a more perfect experience than what they provided to our group!"

Daphne M, sailing the British 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: