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Sail Away

A TradeWinds escape to the Caribbean.

Daily Edit: Sail Away

This is it, the sailing life: sitting on the perch of a 70-foot catamaran in the Atlantic surrounding St. Barths and St. Maarten. The sails are up, the engine is off, and it’s difficult to determine whether the sky or the sea is bluer.

TradeWinds crewed yacht charters might just change the ideal of a resort turnkey vacation. Think of it as a boutique hotel on water where each day, and each destination, is bespoke to you, the customer. Guests can choose to sail anywhere around the Caribbean, the Mediterranean and Ionian Seas, the Canary Islands, or the Pearl Islands archipelago in the Pacific Ocean. With more than 44 boats in its fleet, TradeWinds gives the possibility of buying a membership or booking rooms for a one-off adventure, each of which is fully tailored, from the guests’ food and beverage preferences to their level of adventuring.


Daily Edit: Sail Away


I’m on one particular charter from St. Maarten, and it’s special because this route is where our host Magnus Lewin, the CEO and co-founder of TradeWinds, first chartered sail with guests over 15 years ago. We sail towards St. Barths aboard our yacht, Alive, with stops at Fourche Island and Pinel Island along the way. For avid scuba divers and snorkelers, there is hours of adventure awaiting undersea; the Caribbean is a hotbed of marine activity, with nurse sharks, sea turtles, lion fish, red fish, blue fish, and schools of barracuda suspended in the water, tracking your every move.


Daily Edit: Sail Away


It’s hard not to feel like the 1 per cent with TradeWinds, and when anchoring in the waters around St. Barths you almost expect to hear Robin Leach’s voice, or at least spot a Kardashian on a neighbouring yacht. Onboard cuisine rivals gourmet restaurants, and here it is a pescatarian’s dream regime with lobster, seared tuna, and salmon fillets accompanied by crisp white wines and rosés. Touching down in various ports lend an opportunity to explore the communities on land, which, for us, leads to the discovery of an abandoned Rockefeller property atop the hill on St. Barths’ Colombier Beach. There, like something from Indiana Jones, sits a dilapidated stone dock overgrown by palm trees and brush.


Daily Edit: Sail Away


The property itself has been vacant for over 25 years, and the only way up is over a barbed-wire fence, crushed down by other island explorers. There are rough stone walls, curvilinear lines, and an undulating roof with a simple stone plaque embedded in the wall that reads, “Peggy and Dave Live Here”—the only remaining trace of the lives behind this deserted property. A coral terrace overlooks the bay and the house closes in upon itself around a courtyard. The separated living quarters facing west floor-to-ceiling windows, front row seats for each night’s setting sun. Swimming back to the boat, an evening is well-spent regaling the other guests with our discovery.

TradeWinds has capitalized on two clichés very well: those of being off the beaten path, and creating your own adventure. As Lewin says, it might take some getting used to for land dwellers, but eventually, “you learn to move with the ocean, and appreciate being out to sea.” Life on the water takes on the beat of the sun, early to rise and to drift off as well. It’s a welcome reprieve, learning to escape from urban pressures and allowing nothing but the rhythm of the sea to govern each day.

Photos by Stefania Yarhi.