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The decision to give up the boat is never easy, especially when your health makes the decision for you. This boater seals his legacy with a memorable final cruise.


Bob and Becky sit side by side, sharing a pie at Mystic Pizza. Faded photos from the 1988 rom-com that was shot there hang on every wall. It’s late August, and the town in eastern Connecticut is abuzz with tourists savoring their last bites of summer. The couple, once avid boaters, are just beginning to navigate a new, boatless chapter of their lives.

They sold their Back Cove 41 a couple weeks prior; it was—at least for Bob—one of the cruelest goodbyes he’d ever experienced. Bob Preston is an expert at managing and assessing risk. For decades he spent 55 hours a week weighing risk vs. reward while running the Preston Insurance Agency—a company founded by his father. His Rolodex of customers included prominent boatbuilders, boaters and landlubbers alike.

Deciding whether to provide insurance to a stranger was not simple, but it was straightforward; it’s child’s play compared to assessing yourself, which is exactly what he’s been wrestling with in recent years. When assessing the boating season ahead and the toll his 15-year battle with Parkinson’s disease was having on his body, he was forced to make the dreaded decision of giving up his boat and with it, his most prized pastime.


Thanks to a combination of business acumen and a white-hot brokerage market, in the spring of 2021 he found an eager buyer for his Back Cove 41, Family Ties IV. When negotiating the sale, the new owner agreed to hold off on delivery until August 1st—enough time for Bob and Becky to enjoy one last adventure, a farewell cruise up the coast of Maine.

I met the intrepid couple on the first day of their last season when they took the boat from its winter home in Portland, Connecticut, to its summer slip in Wickford, Rhode Island. The couple, both wearing Spinlock inflatable PFDs, was in lockstep as they worked through their proven pre-departure checklist, which they keep written on a small dry-erase board. Bob checks his electronics as Becky stows their belongings.

Some of the many side effects of Parkinson’s include slowed movement, rigid muscles and impaired posture and balance—all things that make the likelihood of a man-overboard situation much more likely, and ups the difficulty of getting Bob back aboard many times over. Becky appears to wear hers in solidarity.

prm_On His Terms

I offer to make myself helpful during departure but quickly find that they have this practiced choreography down to a smooth waltz. Becky, who is no stranger to driving the boat, swiftly removes the lines and helps guide Bob out of the marina and into the channel. As we settle into a trot down the Connecticut River, Bob and I make small talk about family, boats and the weather. Parkinson’s disease, caused by the degeneration of cells in the nervous system, has left Bob with a significant stutter—a tack-sharp mind physically imprisoned. At times, the stutter is so severe that Becky gently reminds Bob to breath and slow down.

Of all the things Bob is good at, slowing down was never one of them. He was diagnosed with Parkinson’s on July 27, 2006. “The first thing out of my mouth was, Will I be boating in five years?” says Bob from the helm. “They said, We don’t know. You might be on crutches, you might be in a wheelchair. I replied, That doesn’t work for my boating schedule.”

Shortly after his diagnosis, he upgraded from a Back Cove 33 to a 37—better for crossing destinations off their bucket list. Next stop, the Bahamas.

“When a very close friend heard I was doing a 5,000-mile trip, he told me you can’t do that with [Parkinson’s], but it never crossed my mind that I couldn’t do this,” says Bob. “My can-do spirit goes hand-in-hand with optimism. Vince Lombardi said once, ‘You learn to quit; it becomes a habit. So does success.’”

Along their journey to the islands, Bob blogged and shared videos on YouTube aimed at inspiring others fighting chronic illness.

“I wanted to demonstrate how an optimistic outlook is critical in fighting any chronic illness. I wanted to raise awareness about the disease and the 1.5 million Americans like me and to raise funds for the Michael J. Fox Foundation.”


During that journey and subsequent trips, they raised approximately $400,000 for various Parkinson’s charities. After years of successful cruising, inspiring others and raising money with every nautical mile, came the hard reality that his disease had progressed to a point where he could not insure his and his crew’s safety. Risk vs. reward. “While I am still beating back this insidious disease, I have had to make adjustments and give consideration to the effects of Parkinson’s,” began an email I received from him. “My big issue in this instance is remaining a safe boater. All modesty aside, I have had a great record on the water for the better part of the last five decades, that is I’ve never had anyone hurt on my boat and never had to file an insurance claim for doing something really stupid. This perfect record, I fully realize, is in part due to pure luck, but it is also due to the fact that I really worked hard at maintaining a high degree of what I call ‘situational awareness.’ In any event, because of Parkinson’s, I no longer have that (I hate to use the word) gift, but now that I have lost it, I better recognize what a gift it was.”

We’re cruising Long Island Sound when I ask him if he would ever consider doing what so many boaters do, and leave the boat in a slip in perpetuity, giving it a second life as a floating condo.

Through strained speech, Bob explains that staying at the dock was never his cup of tea. He preferred to anchor at a nearby cove or cruise to a favorite destination. To him, staying on a boat chained to the dock would be a reminder of what he couldn’t have anymore: adventure. “My dad used to say, do something with passion or not at all,” he says.

Reflecting on nearly five decades of boating, Bob wrote the following in a Facebook post:

“While Parkinson’s can take physical abilities and mental capacities, it has not touched the memories of navigating Family Ties II, III and IV a conservative total of 21,000 nm through all kinds of weather both good and bad, yes even snowstorms! My wife and I traveled from Canada to the Bahamas, both coasts of Florida as well as many, many of the Florida Keys with hundreds of stops in-between. Here is the thing that amazes me … we did it without a single major breakdown! The repairs were limited to normal routine maintenance such as water pump impellers, windshield wiper motors, sump pumps, fuel pumps and such, but nothing that stopped our travels. This is so unusual in the boating world that it deserves a special thanks to Sabre Yachts/Back Cove Yachts for four quality builds, which is kind of important when your plotted course takes you directly though the ‘Bermuda Triangle’ not just a few times but on many ... occasions.”

Becky hands me her iPad at a table in Mystic to swipe through happy memories made during their mostly uneventful last trip to Maine. She says she’s thankful that they’ve moved on from the boat; the stress of something going wrong or Bob having a health emergency weighed heavily on her. For Bob, the past few weeks have been bittersweet, but he remains steadfast in his decision. The couple holds out hope that their children will get a small boat and that they’ll have a front row seat to their grandchildren spending time on the water.

Bob tells me that he is planning on attending the Newport boat show, proving that you don’t need to own a boat to be a boater.


For most boaters, the decision to give up the boat is made little by little; you use the boat less while fluctuating costs strain a fixed income. That’s what makes the case of Bob Preston so unusual. His time as a boater had a definitive expiration date: August 1, 2021. Time enough for one last hoorah, one more adventure in the watery world he calls home. I worried about Bob and Becky as they began that last trip. They had such high hopes for a satisfying last cruise. And boats being the fickle creatures they are, I hoped a wayward lobster pot or engine issue would not rear its ugly head. Bob deserved the hero’s send off he so deeply desired.

While the idea of a last cruise is heartbreaking, there is also something oddly beautiful about it. I imagine that boating expiration date would make every sunrise and sunset that much more serene, every bite of lobster that much sweeter, every encounter with an old friend or familiar port that much more special.

Some might be tempted to feel bad for Bob, who is being forced to give up his boat while straining to speak through a stutter. Spend even a little bit of time in his orbit, and you’ll quickly realize he doesn’t feel sorry for himself. He considers himself the luckiest man alive. I think that’s something we can all learn from.

This article originally appeared in the November 2021 issue of Power & Motoryacht magazine.