Open seas ahead: How Tradewinds is democratizing luxury sailing

Spending time on a boat begets the urge to spend more time on a boat — or at least it does for me. A couple years ago a cruise around the central Dalmatian islands in Croatia was the start of an itch I scratched in Australia’s Sydney Harbour, when I spent a day on an America’s Cup yacht, and again in Lamu, Kenya, aboard a rustic dhow. It was a lingering itch, so much so that I’ve researched more than once where I can take sailing lessons.

But then there’s the question of the boat. A pricey endeavour, no matter which way you cut it, I thought, until I learned of Tradewinds, which specializes in crewed yacht charters. Typically, chartering a yacht — in Tradewinds case, a luxe catamaran with six cabins — requires getting a handful of friends to commit to vacation together, a destination and agreeing to a week at sea, not exactly an easy feat.  But Tradewinds was founded on the principle that each boat be treated as a small, boutique hotel. Cabins on all boats are booked separately, and start at a US$1,895 per person for an all-inclusive package, about the same for a room at mega resorts that dot the surrounding Caribbean islands. Plus, when you want to get away, there’s no need to wait until family or friends can join you. This means that you’re spending a week at sea with strangers, but that’s not always (ever?) a bad thing. Captain Nathan Shedden, who was steering the 44-foot catamaran I took around the British Virgin Islands, remarked that the best trips he has experienced are when people book rooms separately, starting the week as strangers and ending as friends. Families travelling together can sometimes forget to leave their emotional baggage on shore.

It may seem a bit much to some to spend a week in extremely close quarters with a group of strangers, but the trips themselves require travellers to be relaxed and up for anything — beyond the start and end points, the itinerary is set at the discretion of the wind and water. If you’re someone who likes to plan a vacation as strictly as your workday, you may find the spontaneity of a week at sea less than relaxing.

But if you are open to whatever comes your way, this style of travel could become a way of life. Indeed, for many it has: Tradewinds offers lifetime memberships starting at US$10,000 that give priority access to vessels and routes, including time on Wanderlust, a yacht that is navigating the globe. Currently, the company offers trips throughout the Caribbean and French Polynesia as well as Greece and Turkey.

Tradewinds luxury catamaran

During my time on the boat, I met a former war documentographer who spoke openly about the conflicts he’d covered and how he overcame post-traumatic stress disorder. He also put this English major to shame with his literary knowledge, which included citing Norman Island, our first stop in the British Virgin Islands, as the inspiration for Treasure Island. Another passenger and I bonded over career changes and a love of photography. We kayaked together during the afternoon, compared photos in the evenings and, though it’s been weeks since the trip, we still keep in touch.

Also on board was Tradewinds co-founder Magnus Lewin and his wife, April. During one afternoon sailing, I mentioned that I’d spotted a boat bearing the name Necker, the name of the island owned by Richard Branson. Lewin confirmed that that was one of Branson’s vessels and then shared the story of how the head of Virgin came to own an island: Branson went island shopping, as one does, while trying to impress a woman. When asked if he’d like to make an offer on anything he saw, he lobbed an extreme low ball figure, and… crickets. But then a few years later when the owner was forced to sell or have the land claimed by the government, Branson got his island for the price he wanted. Stick to your guns, was the morale of the Lewin’s story, a philosophy that has all the more meaning given that’s what he did when in 1998, when he built a 45-foot catamaran in Durban, South Africa, then sailed it to Saint Martin and launched Tradewinds.

Between the time spent getting to know my fellow passengers, I spent time swimming, snorkelling, diving and beaches to explore. There was bubbly and gourmet meals, made all the more impressive given the tiny kitchen they came from, and a seemingly never-ending happy hour.

I didn’t know what I was getting into when I boarded the yacht on day one, but now know that I am already looking forward to travelling this way again, and that my sailing itch may have found its cure.

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