Sailing into Retirement

They say you should phase in retirement and not do it cold turkey. John LaBossiere and his wife Trish have figured it out.

They returned from a sail last spring on the York River to convey the new details of his retirement plan. He is finishing up work on his US Coast Guard captain’s license and will put their vintage 30-foot Pearson into charter on Rhode Island Sound, near their home in Narragansett.

Trish figures the season there is only seven weeks, while John stretches it to ten. Here’s the kicker. They’re looking to buy a newer 39-foot Beneteau on the Florida Gulf and letting a charter company put it out all year long. “That way,” John said, “I can get some income during the year and then go down there in the winter and run the charter myself.” That’s an ingenious blend of the classic Moorings charter concept with the DIY skipper concept. Meanwhile, he spends part of the summer on the other boat.

Sailing into RetirementWe talked at length about the challenges of chartering one’s own boat locally. Trish posed an intriguing question. “He loves sailing so much that I worry it would get old by going out more frequently. It’s like owning a pool.” She has a point, but not for me. I have found every day to be invigorating because of the work. “I get to meet fascinating people from all walks of life. They are professionals, creative, well-informed, lively and outgoing.”

“Like us,” Trish quipped. “What about no-shows?” I had one last year.

She asked what surprised me about chartering, and I said it was the adventure. “People want to do something new and bold on vacation.”

John was also concerned that the Pearson might not be as ship shape as he’d like. He stole it for $3,300 and had it refitted with a roller furling jib. I proffered that people don’t care as much about the boat as they do the scenery and the experience. If they have a good time sailing, the boat’s performance matters more than appearance.

I’ve sailed on some charter dogs. Last winter my wife and I were on a dog that ran up and down a Florida stretch at Punta Gorda. The sails were up but we never sailed because we had to stay in the channel. Yet it was a wonderful time because the captain was delightful and the scenery grand.

Sailing into RetirementTrish was using the binoculars to look at the scenery as the wind blew a steady 10 mph and the sun began to set. “Look!” I pointed.
An osprey just caught a fish.”

John has the best of both worlds already. “I love my job as a home inspector, and I love to sail.” If he phases out by working fewer days a week, he can spend those days chartering in Rhode Island. Then he can take some time off in the winter to do likewise in Florida. Why didn’t I think of that?

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