Plan a Private Cruise and Sail Away Safely

A Caribbean yachting adventure is like a week-long dinner party at a friend’s house.

By Loren Christie   |   March 09, 2021

Ah, the sailor’s life. Time spent loafing aboard JimJams couldn’t be more simple or more relaxing.

Within one minute of boarding the JimJams, I have a glass of champagne in hand and I’m being warmly welcomed by our captain, Andre de Klerk, and his first mate and life partner, Mareike Eichhorn. “Call me Mickey,” she says with a slight German accent.

When I woke up that morning in my hotel room on the east side of St. Maarten, the wind had whipped up the waves and it was whitecaps as far as the eye could see. A TradeWinds yachting trip around St. Maarten and St. Barths had sounded like a dream, but now I was quite sure that everyone on this Caribbean sailing adventure was destined to be seasick. 


Small ships are like a private hotel that you can hub and spoke off all day.

A paddleboard doubles as a pop-up swim-up bar, while the boat's hydraulic lift becomes a dumb waiter.

Water World
Private marine adventure is a chance to take your shoes off for a few days, tune out and enjoy the simple pleasures of the sea. TradeWinds offers multiple sea and land packages throughout the Caribbean, the South Pacific, the Mediterranean and Central America.

JimJams is a 60-foot catamaran with four cabins, each with its own bathroom and shower. Although they are her crew, not her owners, Andre and Mickey refer to JimJams lovingly as their baby. As we board, Andre tells us that because of the wind, we’re no longer going to St. Barths but will head to Anguilla instead, where we will have a much smoother sail. I like them both immediately.

As Andre makes us pre-dinner drinks, he says that the first night is for getting to know each other and that safety procedures will be reviewed in depth before we set sail in the morning. For now, his only request is that we relax and take off our shoes, which I do. And they will stay off until I disembark a few days later.

There are a surprising number of activities available for those who wish to partake: there’s a standup paddleboard, a kayak, fishing and scuba gear. Our group mostly avails ourselves of the opportunities to snorkel. Crocus Bay on Anguilla is the best, where we see sea turtles, eels, flying stingrays and brightly coloured fish of all sizes.

On the second night, we partake of a TradeWinds tradition—the pop-up swim-up bar. Floating off the back of the boat on pool noodles, we sidle up to a paddleboard, which is doubling as a counter. The JimJams hydraulic lift becomes a dumb waiter for Andre and Mickey to deliver smoked salmon hors d’oeuvres and pitchers of Amaretto sours as we float along. After a few drinks in our bathing suits, our inhibitions reach appropriate vacation level and we serenade our hosts, butchering Celine Dion’s “It’s All Coming Back to Me Now”—with accompanying grand hand gestures, of course.

It’s hard not to help Andre and Mickey as they work to keep everything literally shipshape. My partner does things like tie up the dinghy and gather snorkel equipment, but it’s not an expectation. “We want guests to feel like they have come to a week-long dinner party in our home,” Mickey says. For us, when we have dinner with new friends, we do like to at least clear the table. But like everything else on this fine boat, you do whatever makes you comfortable.

Loren Christie

Loren is the travel expert on CTV’s Your Morning. He previously appeared on Canada AM and wrote a travel column for Metro newspapers. He contributes to multiple travel magazines, radio programs and websites.

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