The sky’s the limit aboard Pantera; Captain Ewout Franse (and the boat) stay on an even keel.

"Permission to jump, Captain?”

Looking out at the aquamarine water in Little Bay, a peaceful cove in Anguilla’s Little Bay Marine Park, I’m not sure I’ve heard the question correctly from our first mate, Simone Embacher. Why would anyone want to abandon ship when it’s a 56-foot catamaran sailing the Caribbean?

Our calm and capable captain, Ewout Franse, answers with a nod. “We’re in the clear to swim!” says Embacher and gives the anchor line one last tug on its cleat before ducking below deck to shake up some cocktails. Within minutes, we’re all bobbing atop gentle swells, drinks in hand, to toast our first day at sea.

Of course, sailing goes especially smooth with a crew like Franse and Embacher at the helm. The couple are so at ease running the vessel, part of the TradeWinds fleet, that I wonder if they weren’t cradled in it since birth. During our five-day excursion around Anguilla and the Dutch-French island of Sint Maarten/Saint-Martin, it feels like I’m bunking in with good friends, only ones who know where to find the best hidden beaches and which wines to pair with our three-course dinners. (Embacher is a trained sommelier, chef and dive master.) In their hands, Pantera – our nimble boat – moonlights as a cozy sleeping nook, tour bus, stargazing lookout, scuba diving headquarters and alfresco restaurant. But even with all the amenities (yep, there’s a fully stocked built-in bar), we’re worlds away from the luxury resorts twinkling back at us from the shoreline. Rather than wander aimlessly from spa to restaurant to beach, we get to choose our own adventure – or sometimes it chooses us.

Anguilla shows its true blue colours.

One morning, the sinuous stretch of sand that makes up Anguilla takes on a new dynamic as we zip by at 10 knots (18 kilometres an hour). Rounding the western tip of the island, we cut south to St. Martin under blue skies; then, suddenly, a rain shower erupts. The waves buck and fizz, slide side to side and swing us up in a drunken two-step, a rhythm that becomes strangely comforting and hard to shake back on land.

As I get a feel for the boat from behind the wheel, Franse shares some nautical tips while securing a baited fishing-pole line to the stern (just in case a hungry tuna or mahi-mahi should pass by). “A flappy sail is an unhappy sail,” he tells me before jumping over to hem in the jib and create a nice crisp sheet. Use what you need and trim the rest, which makes sense aboard Pantera, the very model of efficiency. Unlike some of the Goliath cruise ships and megayachts we see chugging along at a snail’s pace, our catamaran can drift into the shallowest of waters – a good thing, since parts of Anguilla’s coast can only be reached by small sailboat or airplane. Each morning after breakfast, when Franse and Embacher pull out the charts and pinpoint the day’s destinations, we have to lean in close to spot the specks of sand detailed on the map. Their version of island-hopping is truly off the grid.

At nap time, the catamaran’s trampoline makes for the ultimate hammock.

Later that day, when we drop anchor in Grand Case, St. Martin, to explore the French town’s weekly night market, I realize it’s the first time I’ve put on shoes since boarding – and, let’s be honest, taken a shower. Finding our land legs, we stroll along the main street in a fog of grilled-meat smoke rising from the roadside barbecue stands, a.k.a. lolos. But, almost instinctively, we turn back toward the water and settle at the beachfront Calmos Café, where tables sink askew into the sand and servers sport T-shirts scrawled with “C’est la vie.” A few rounds of the house rum punch, and I agree: This is the life.

Before tucking in for the night, we huddle together on Pantera’s trampoline, a swath of mesh stretched between the twin hulls like a giant hammock. The halyards clink gently on the mast, and the waves plunk out a steady bass line below us. There’s a certain simplicity to staying on a boat. The lifelines become makeshift clotheslines for drying towels and swimsuits, and our leftovers go to feeding the fish each night. (Embacher makes sure everyone eats well.)

Captain Franse takes the wheel and keeps an eye on the tell tales - three ribbons attached to the sails that show the wind’s direction.

From here, every new port starts to feel familiar, and playing Master and Commander has made the stretch of blue before me seem almost conquerable. Fix upon a point on the horizon, hoist the sails and ahoy! But diving off Tintamarre, an uninhabited island east of St. Martin, is a quick reminder that I’m still a small fish in a very big, very deep pond, thanks to the three Jurassic-looking tarpon that just swooshed by. Not much has changed down here in the 250 years since the small atoll had its own king, then serviced the French Navy and, eventually, got its own seaplane airline. Following a spotted eagle ray’s lead as it skims the sandy bottom, I simply go with the flow. (If learning the sailing ropes has taught me anything, it’s how to unwind.)

The approach seems to work equally well on land at nearby Pinel Island, where the fields of blond grass leading up to dramatic peaks create a Caribbean pastoral by way of Provence. Looking across Cul-de-Sac Bay to St. Martin, I wonder how, according to legend, Christopher Columbus had time to name the island but not touch foot on its shores. Clearly he missed out, judging by the day trippers taking a leisurely snorkel or sipping guavaberry cocktails at one of Pinel’s two restaurants.

When the umbrellas are cleared it’s time for a guavaberry cocktail back on the boat.

To celebrate our final night, our crew has a picnic on the beach while the day wraps up. The little wharf fills with people ready to be ferried back to the mainland. A dog chases each departing boat with a farewell bark. Hang-gliders drift back down to earth, and the sun melts into the horizon. Motoring back out to Pantera in a rubber dinghy, I think about Franse’s adage, “A flappy sail is an unhappy sail.” It must apply to sailors as well: Too much slack, and we long for adventure at sea. Climbing aboard the boat, I know the drill: I ask if I can jump and then cannonball into the water.

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St. Maarten
Starting December 17, Air Canada offers one weekly non-stop flight to St. Maarten from Toronto, featuring convenient Saturday service. From there, take a taxi to the Port de Plaisance marina.