We all dream of living like the rich and famous, but when travelling with TradeWinds, that dream isn’t too far out of reach. On a next-level sailing and villa adventure, MEGAN HONAN discovers what luxury can look like in the Caribbean.


The trip did not start as planned: I was heading to the Caribbean for five days
sailing from lush island to lush island aboard a luxury catamaran. But then, an announcement by the captain: “ATTENTION: we will be landing due to mechanical failure.”

I could have cried.

Instead of Saint Vincent and the Grenadines, I found myself landed in Barbados – and without a plan. But if there was ever to be a detour en route to paradise, another paradise would suffice.

After a few phone calls and thanks to a friend of a friend, I got myself sorted for the near 20-hour layover before moving on to my final destination. I made my way past pastel-colour homes with white picket fences and swaying palm trees before checking into The Crane Resort, a St. Philip institution that has reigned supreme since 1887. I was greeted by two beaming faces who instantly took my luggage and said, “Welcome, we’re so glad you are here!”

It was a long day of travel with more than anticipated hiccups. I was happy to be there, too.


After whiling away most of the next day with toes in sand and drink in hand, I hopped on a six-passenger plane to the Grenadines.

By the time the sun was setting, I was aboard a TradeWinds catamaran yacht with a cocktail in one hand and seven new friends around me. Among them was Magnus Lewin who is the CEO and co-founder of TradeWinds but far from your typical corporate guy. Sporting long shaggy hair and a breezy linen shirt, you’d expect him to greet you with a shaka rather than a handshake.

TradeWinds was founded in 1999, born out of the idea that luxury, all-inclusive sailing excursions should be accessible and affordable. Today, Magnus can be frequently found in the Caribbean, drawn by the natural beauty and strategic location for launching TradeWinds’ fleet of catamarans.

Upon meeting, we wasted no time in entertaining ourselves the old-fashioned way: through good conversation. As seemingly endless bottles of wine flowed, the topics bounced from light-hearted stories to serious matters of the heart. By the time I finally made my way into my cabin below deck, I wasn’t sure if it was the waves, wine or exhaustion that rocked me into the deepest sleep of my life.

I awoke to my first true taste of TradeWinds life. A breakfast spread more suited for a queen was laid out on the deck – fresh omelettes, sweet smelling bread, yoghurt parfaits, fruit, bacon and piping hot tea made it all but impossible to not overindulge. And the royal treatment didn’t stop there. I spent hours on end lying out front of the ship, book in one hand and beer in the other. Just as I’d finish one bottle, a crew member would seemingly appear out of nowhere to ask if I’d like another. Why yes, I would.


Located somewhere in the Windward Islands lie the Grenadine’s best-kept secret: Petit St. Vincent. The private island is a luxe, secluded paradise only accessible by boat. With just 22 private villas tucked into the hillside, it’s almost easy to forget an outside world exists, which is exactly what makes it popular with the rich and famous – and the perfect spot for lunch. As we docked at Goatie’s bar, I noticed the bartenders without shoes and a sign naming it the 2018 Andrew Harper’s Members’ Choice Award for the best place to unplug from the wired world. This was exactly what I was learning to love about the Grenadines: relaxed luxury was the name of the game.

But if Petit St. Vincent was paradise, then Mayreau– the smallest of the Grenadines islands – is utopia. It’s also the home of TRIBU Villas, TradeWinds’ latest venture labelled the “Aqua-Terra experience,” as guests can now spend time being pampered both on water and land. The five-bedroom villa is decked out in island-luxe furniture imported from Bali, along with a private beach and a million-dollar view. Soon, there will be a new set of villas on the land next door, along with a beach club; the TradeWinds family is always expanding.

Our own little family of travellers spent our remaining days soaking up as much sun as possible on the loungers or snorkelling the nearby reefs where we’d float, lost in a state of wonder among the turtles and blue starfish. Over dinner every night, we’d repeatedly say, “This is the life,” or, “Can we just stay a little longer?” Now that we’d seen how the one per cent lives, it felt almost impossible to go back.

As I returned from my last morning swim, I was greeted by our private butler, Kara, who was always so enthusiastic to talk about Mayreau and its people. “Welcome home,” she’d say, as if I’d already lived here in another life.

I hope I had.