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A Week On Board a Crewed Yacht Charter Around the Caribbean

Chasing after a sea turtle, grinning like a maniac behind my snorkel, all I could think was, “That turtle is my best friend!” This is the kind of slap-happy thinking that occurs when you’re hundreds of miles from home, sailing on a 57ft luxury catamaran in the so-blue-it-can’t-possibly-be-real waters of the Caribbean.
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Chasing after a sea turtle, grinning like a maniac behind my snorkel, all I could think was, “That turtle is my best friend!”

This is the kind of slap-happy thinking that occurs when you’re hundreds of miles from home, sailing on a 57ft luxury catamaran in the so-blue-it-can’t-possibly-be-real waters of the Caribbean. As I swam along with my new best friend, snapping pictures and watching him play with other sea turtles along the ocean floor, I realized that this kind of experience was unlike the many others I’ve had sailing. Not only was it my first charter, my first trip to the Caribbean, my first time on a catamaran, it was also the first time I finally “got it”—the first time I understood why people do this, why they spend their time, energy and money pursuing this dream.

There are many different ways to sail in the Caribbean. Mine happened to be a weeklong, all inclusive, crewed charter with TradeWinds, which departed out of St. Maarten and then sailed around St. Barts and Anguilla before returning to St. Maarten. It was an entire week of eating, sleeping, drinking, playing and lounging, all aboard a Fountaine Pajot Sanya 57 called, believe it or not, Dream Maker.

The majority of the people who book these vacations are couples. But I booked mine with my oldest friend, because we live on opposite sides of the country and needed a chance to reconnect with each other (and ourselves) far away from our families, jobs and the demands of daily life.

In planning for the trip, we didn’t know what to expect, so we turned to the Internet for help. We exchanged countless emails and instant messages and Facebook posts with links to, stories about people lost at sea, movies like Open Water, and songs like “Sailing” by Christopher Cross and “I’m On a Boat” by the Lonely Island. Thank you, Internet, for preparing us in the best and worst ways possible.

As it turns out, nothing can really prepare you for it a trip like this, not even Christopher Cross, because it is almost too good to be true. Every morning you wake up feeling better rested than you have since you were in the womb, to a fresh, delicious breakfast prepared by some magical creature, anchored in waters that seem too beautiful for mere mortals. After that, guess what happens? Someone else cleans up! You eat and drink as much as you want, stand up, go down to your cabin, change into your swimsuit (unless you were already wearing it as I often was), slather on sunscreen and spend the rest of your morning doing whatever your heart pleases. Maybe it’s sitting on the deck enjoying the breeze. Maybe it’s helping the crew prepare the boat for sailing. Maybe it’s taking a quick swim in the ocean, checking in with Turtle, seeing what he’s up to this fine morning.

Whatever it is, it isn’t dealing with the hassles of a bareboat, where you’re responsible for everything, from sailing to provisioning to clearing customs to repair and maintenance. On a crewed charter, you simply show up with your soft duffel full of swimsuits and shorts, your passport, your camera and a mindset of leisure. Everything is taken care of. If you want to participate in the sailing itself, your captain is happy to let you hoist the sails, take the helm, set the anchor, gybe, you name it. I myself preferred to watch the action from the seats at the forward end of the bow, drink in hand, silently critiquing, soaking it all in.

Our crew were Guy and Rose, the cutest couple you’ve ever seen. (It seems to be standard with TradeWinds that your captain and first mate are not only a couple, but also adorable.) Guy was just a boy, barely out of diapers, but he was a captain in every sense of the word, and Rose was a whiz in the galley, always ready with a warm smile, a drink, and delicious-tasting food. Together they took great care of both the boat and their guests—all 10 of us. They fed us, listened to our stories, answered our questions, arranged shore excursions and regaled us with their own tales of sailing all over the world. Click here for Rose's Caribbean Chicken Salad Recipe

We were also especially lucky to have Lize and Chandré on board, a couple of crew trainees from South Africa—worthy rivals to Guy and Rose for Cutest People Alive award. This was their final training charter before they took over their own boat, and the two of them shared the smallest possible space on board, an area about the size of a bathtub. Nonetheless, they were happy as can be, all smiles all the time. Clearly TradeWinds isn’t just heaven for the guests.

Our first morning aboard, Guy gathered us all around to plot our “itinerary,” as soon as we’d finished a fresh fruit breakfast. (I use quotes because TradeWinds is happy to adjust its charters based on the guests’ preferences, especially if a single group books an entire boat.) Our week started out a bit shaky, with a long afternoon motor that left several of us queasy, but took a turn for the better when we were treated to a gorgeous starry night in Île Fourchue. The second stop was St. Barts, where we tied up in Gustavia’s famous pink and turquoise anchorage and wandered around the upscale little town and its fancy shops.

Stop three was in Grand Case, on the charming French side of St. Martin—think Pirates of the Caribbean and warm, wide smiles—where we enjoyed a fantastic dinner at Ocean 82. The fourth stop involved the longest sail of the trip, up around the east side of the British-owned Anguilla. It was here I got to play photo journalist for a bit, as Chandré and I rode around on the dingy, chase-boat style, to get some shots of Dream Maker under sail. Man, can she move!

The cat itself was beautiful: 57 feet of well-maintained luxury and comfort. My favorite accoutrements were the bright, colorful beanbags secured to the deck next to the trampolines, where you could get comfy and relax, watching the ocean pass by as we sailed from one anchorage to the next. I also loved the state-of-the-art sound system on which guests took turns playing their favorite sailing playlists. (John Mayer seems to have cornered the market on charter vacation soundtracks.)

Dream Maker came equipped with plenty of toys to keep us entertained: kayaks, SUPs, swim noodles, fishing poles, snorkel and diving gear—you name it, it was on that boat. And if it wasn’t, and you made mention of it, chances were the crew would find a way to get it. Once, Guy overheard one of the guests, Jeremy, talking about his favorite vacation drink. Sure enough, after the next provisioning stop, Guy returned to the boat with the Jeremy’s favorite in hand: coconut water and rum!

The fifth night of the trip was my favorite, when we anchored in Maundays Bay on Anguilla, next to an exclusive resort and the most gorgeous white sand beach you can imagine. Our final night brought us back to the beginning, anchored outside St. Maarten in Simpson Bay, where we shared a final meal on shore and said our goodbyes.

When people ask me about my charter, it is hard to name one specific incident that really stood out. Was it when a TradeWinds dinghy was stolen during dinner in Grand Case, only to be recovered by a pair of locals who were on the lookout, and only too happy to be rewarded with two bottles of wine? Was it hiking up the mountain in Little Bay and overlooking the harbor where we were anchored, seeing miles of stunning ocean and sky? Maybe it was sunning on the gorgeous white beach on Anguilla. Or enjoying the warm ocean breeze as we traveled the seas with full sails and hearts. Could it have been the amazing sunsets? Don’t forget all the swimming and snorkeling. The food? Oh! The food. I could go on and on about the food. (So could my waistline.) Maybe it was the ocean of stars above us, gently reflected on the ocean below, making me wonder about all the other sailors who have looked up on those same stars for centuries before.

But wait—I haven’t yet mentioned the people, the other guests who may very well have been the best part of the trip. First there were Gregg and Pam from New York & Florida, who kindly lent me their underwater camera to take pictures of the Turtle. Then there were Jim and Linda from North Carolina, who were on their second week of TradeWinds charters and therefore my personal TradeWinds experts. Mike and Michele were a couple of Italians from New Jersey who endearingly fit that stereotype to a T and kept us laughing all week. And let’s not forget German Katrin and her husband, Jeremy, a couple closer in age to my friend and I, from Northern California. Katrin kept active with yoga and SUPing, while Jeremy made sure to keep the fishing lines locked and loaded, and his glass full. Truly, my fellow guests were a diverse and fun group.

And then there were the unexpected moments of inescapable beauty and quiet reflection that I hope will remain with me forever. Memory is a tricky thing. So many months later, as I think back, I find myself forgetting some things. Maybe those moments don’t belong to me anymore, I think, as I feel my grasp loosening on them, losing their shape and their form. But then I only need to close my eyes and realize they’re still with me. All those seemingly insignificant moments on the boat, the solitude, the laughter and the toasts, the salty skin and tanned faces—they are now all a part of me, so that to this very day, even in my land-based bed, I need only close my eyes and I am once again swimming with my friend the Turtle. Thanks, Dream Maker


Charter company: TradeWinds,; 844-210-8275

TradeWinds is a members program with its own “ internal currency” called Plus Points. You don’t need to be a member to book, but membership offers savings and flexibility. Every charter includes a presentation, where you learn about the program (if you’re not a member), discover new features and destinations, and purchase Plus Points. Note: the only time you can become a member and purchase TradeWinds Plus Points is aboard the charter boat.

They offer three different classes of catamarans (all Fountaine Pajots): Flagship, Luxury and Cruising, which are fully crewed and all inclusive. No need to worry about provisioning or clearing customs! Do be prepared to tip your crew though, they work hard!

TradeWinds currently operates charter bases in the British Virgin Islands, St. Maarten, Antigua, Guadeloupe, St. Vincent and the Grenadines, Tobago, Panama, Belize, The Canary Islands, Greece and Turkey. Rates vary based on low and high seasons



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