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Our TradeWinds catamaran cruise leaves from Guadeloupe.
Our TradeWinds catamaran cruise leaves from Guadeloupe.

Sail on a catamaran (not a cruise ship) to explore tiny Caribbean outposts Add to ...

Perched on the starboard bow of New Beginnings catamaran, with my legs dangling over the Caribbean Sea off the coast of Guadeloupe, I watch a school of fire-engine-red parrot fish glide through the blue beneath my feet. Knowing the water is nearly as warm as the soft air, I dive in after the fish and swim to the uninhabited lush green island of Îles de la Petite Terre, where we have been anchored since last night. In a few hours, the oasis will be crawling with snorkel-gear-toting tourists attracted by the coral reef nature reserve framing the island. But right now, we have the place to ourselves.

There are cruise people and then there are people who want to explore multiple destinations without a crowd. Sailing on a small intimate yacht like New Beginnings is for the latter group. New Beginnings is part of the TradeWinds Cruise Club, which at the minute is the only outfit providing this experience at a luxury level. You can rent a cabin and sail with a group of like-minded travellers, or you can charter the entire vessel. There are TradeWinds yachts scattered throughout the Caribbean, Greece and Turkey, and itineraries typically run a week, stringing together secret discoveries like uninhabited beaches, unspoiled villages and crowd-free snorkelling spots.

I'm with a group of six friends who make up the guest list of the 70-foot Galathea catamaran. She's plush and treats us well with queen beds and private ensuite baths.

I'm not used to such luxe on the open seas. As a fisherman's daughter from British Columbia, I've spent lots of time on the ocean, but I've always been working. So this week, while my friends take lessons on steering the boat, tying knots, laying anchor and setting the sails, I'm happy to leave everything to the capable crew. And when I say everything, I am including paddling to the local French grocer for fresh baguettes, mixing a new Caribbean cocktail every evening, playing DJ and baiting hooks during afternoon fishing adventures. Sadly all we catch is a metre-long barracuda – it's beautiful, but not fit for eating. We give it back to the sea.

Our itinerary goes something like this: We sail from Guadeloupe through the surrounding French islands, including Marie-Galante and Îles des Saintes, Îlet du Gosier and back to Guadeloupe, tucking into various points along the way. I feel like an early explorer, mapping out my new colony, and tie a bandana around my head for dramatic effect.

For me, the week is a mix of decadence and adventure. I wake with the sun and climb the few stairs up to the main deck, where breakfast of fresh tropical fruit, granola and yogurt are already waiting. “It's another beautiful day in paradise,” Captain Mick says after the meal. He's describing the day's plans, pointing out the route we'll take to our next secret hideaway. I can't argue with his outlook. While my friends lower themselves into kayaks to explore the mangrove overhangs lining the islands, looking for mongoose and wild ducks, I wade ashore and bushwhack into the jungle, careful not to step on any critters lining the forest floor. I allow myself to think I'd do okay being stranded on this deserted tropical island. Easy to say when New Beginnings is tethered close by.

On board there's enough room for people to gather or get away on their own. Two seats at the ship's prow prove to be the most popular spot for us to ride the waves, yelping with each big splash, trying to dip our legs into the water. The boat is one big bed on floats. I move from trampoline to chaise longue to over-the-water netting, never short of a place to settle. When too hot for comfort, we dive from the bow into the cool water below. At night, we swim through the dark and our strokes start the water glowing phosphorescent, twinkling around our fingers and toes as we move.

In the small group of islands known as Îles des Saintes, we tender into the little French fishing village of Bourg des Saintes. Bright coach houses line the narrow streets, and rowboats anchored in the harbour are painted in vivid teals, oranges and reds. This piece of France (I swear I hear someone wearing a striped shirt and beret sing, “Oui, oui mon chérie”) is folded against a fertile mountainside smack in the most luscious of the Caribbean. It's here my fellow sailors let off steam and rent scooters to explore the island.

We set off, looking silly in mismatched, ill-fitting helmets, giggling our way through the village and countryside, locals waving as we putt-putt by. We drive up to the mountaintop to explore Le Chameau, an old lookout tower, and Fort Napoleon, a former jail-turned-museum. We cross town and zoom up the other side, passing goats, donkeys, horses and makeshift gardens overlooking a turquoise sea and volcanic island archipelago. After cruising down a one-way street past what feels like the entire village frowning and shaking their fingers at us, we call it quits. After admiring the sunset, we head back to New Beginnings for a feast of lobster and chardonnay.

Aside from the odd tomfoolery, most days are spent dropping anchor in a secluded bay for an afternoon of basking and swimming and playing Robinson Crusoe. I want all my new beginnings to be just like this.

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