Former hitchhiker of the ’80s embraces Miami’s sailing life

Meet Jim Hesketh, 65, of Miami, who is self-employed and owns a 1978 C&C 26 with two other people. The boat is called Whisper. He usually goes out with his two partners on the boat, his wife Zaydee and friends.

“I love taking people for their first sails out on Biscayne Bay to show them a side of Miami many have not seen yet,” he said.

“Miami does look best from the wet-side of the high-tide line.”

What do you like best about your boat?
It sails so nicely and easily — I sometimes take it out alone if I’ve only got an hour to spend.
I motor out the slip and head out one channel, return in another and sail it back into the slip. That can be as much fun and as satisfying as a long sail. It’s a good way to keep my head clear.

What do you like least about your boat?
She is an old girl and has needed some major attention the past few years with the mast step and bulkheads needing to be rebuilt. I had to remove and reseal all deck hardware, deal with wiring issues, etc.
It’s satisfying work and I can do it myself. But sailing is more fun

How did you take up boating?
In Seattle, my hometown, I had a run of bad luck in 1980, which included losing most of my possessions in a house fire. I was a young, adventurous 23-year-old so with nothing to hold me back, I set out on a year-long hitchhiking trip.
On one of my “rides,” I helped bring a 30-foot trimaran up from Key Largo to Coconut Grove.
My life has been centered around sailing and Dinner Key Marina since that day.

What do you most enjoy about being on the water?
It just feels like where I belong.

Where was your most recent outing?
Bay sailing. We might wander down through the keys this winter or spring.

Favorite places to go in your boat?
Biscayne Bay, the keys.

What is your one must have item during trips?
The “off” switch on my phone.

What has been your most challenging boating experience?
Probably the few times I crewed for others on race boats. That level of intensity isn’t what I'm seeking when sailing, and it took me a while to accept that there was an element of the sport I didn’t really enjoy.

What would be your dream boat?
A Concordia yawl, not the simplest option when it comes to sailing, but I’m a sucker for the book “Romance of the Sea” and these classic wooden boats speak to that emotion.

Best advice to new boaters?
Learn everything you can and keep it — the boat and your dreams — as simple as possible.
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