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Thimble Islands | Tour Connecticut's Vacation Retreat

Thimble Islands | Tour Connecticut’s Vacation Retreat
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Captain Bob took to the water as a teen. “As a kid you could always work on the islands,” he told me. He began by hauling garbage—“I know the backs of all these houses,” he notes wryly—and at age 14 worked aboard the small private ferry and tour service that operated from the town dock. He started the lifelong endeavor of accumulating information about the islands, their residents, and the complicated relations between the two. (Growing up, he said, “it was Creekers and Islanders. Once in a while we’d mix. But they had nicer boats, and we had old dories.”)
As he grew into adulthood, the sea persisted in its allure, and he left Connecticut for Maine to study marine biology. But he arrived at a sad realization: “I had to take, like, four years of biology classes before I could even get on a boat.” He deemed that un­acceptable, so he switched to classes in navigation and mechanics, aiming to become a deckhand on a large ship. He learned much, but economic cycles didn’t cooperate; shipping was in the doldrums when he graduated, so he headed home. Here, he discovered that the tour and ferry business he’d worked for as a teen was for sale. With help from the owner, he bought it in 1986.

Captain Bob initially ran the operation much as his predecessor had: Both tourists and ferry passengers would board at the same time and take the same trip. But that led to complications—the least of which were the ceaseless complaints from islanders who just wanted to get to their homes without detouring around Cut-in-Two, and who had grown weary hearing about Tom Thumb and his diminutive girlfriend, Miss Emily, for the millionth time. So in 1989 he split the business and bought a smaller launch devoted to ferrying passengers. He eventually sold the ferry business and kept the tour business for himself.

\He pilots and narrates all tours himself, as many as six a day. “The basic stories and basic information stay the same,” he says, “but I try to ad-lib now and again.” After unloading one group, he’s usually got 10 minutes to grab a cigarette on the dock before starting out again. “I try to do a good tour every time,” he adds.

Competition among harbor tours has surfaced over the years; there’s a bigger, flashier tour boat with an upper deck more suitable for sunning and yakking, and you can now tour by sea kayak as well. But few know the harbor’s history and people from personal experience like Captain Bob.

“Just seven of the islands have electricity,” he explains to his passengers as we motor past Rogers Island. “And most of the islands prefer not to.” Most islanders, in short, opt for a quiet, unplugged life. Rogers, however, doesn’t, Captain Bob goes on: It has a 27-room faux-Tudor mansion with swimming pool, tennis court, badminton court, greenhouse, and tiny six-hole golf course. Palm trees in oversized planters—they overwinter in the greenhouse—dot the island’s periphery, provoking one passenger to wonder what time the luau starts. Others on the boat cluck their tongues in astonishment when Captain Bob notes that the unnamed owner bought it about a decade ago, paying more than $22.3 million.

Facts are the raw material that any guide uses, but a good guide tells a story that’s as intricately crafted as a New Yorker piece: There are themes, illustrated with anecdotes, arriving eventually at a conclusion. Among the recurrent themes Captain Bob explores is the fragility of the islands in the face of wrathful nature. He often mentions Hurricane Irene, which in 2011 sent a sea surge up Long Island Sound, along with howling winds that wrecked many of the precariously sited homes. He points out some of the damage that has yet to be repaired—an effort only complicated by 2012’s Hurricane Sandy storm surge.

But he’s even more voluble about the 1938 hurricane that served as a sort of final curtain to the golden age of the Connecticut coastal resort. That immensely powerful storm raked many islands clean, crumbled sea walls, and took lives. It took weeks just to assess the full damage. And it came at a perfectly dreadful juncture for rebuilding the travel trade: Tourists no longer traveled by rail and steamship; they now gadded about in motorcars. So they went up to Cape Cod, Captain Bob tells the passengers, “where they’re still stuck in traffic.”

But the wealthy eventually came back during the go-go years of the 1980s and started buying up the islands. Captain Bob agrees with my observation that the islands now seem to be amid a sort of second Gilded Age. Which suits him fine for professional purposes; another theme he deftly riffs on is the folly of wealth. The moneyed crowd may own a lot of pelf, but the rest of us are bequeathed stories about their foolishness. Palm trees in Connecticut? Cue the guffaw.

He riffs again as we pass Cedar Rock, a small knob purchased by a man with plans to build a house with 360-degree views. The new owner then made an unfortunate discovery: The islands now require at least an acre and a building lot at least 12 feet above high tide before granting a permit. So a temporary, open gazebo now sits on a rough pile of rock, looking self-conscious and, frankly, a little silly. “You’re looking at one man’s version of paradise,” Captain Bob narrates dryly. “Paradise is for sale—and it can be yours for $285,000.” Everyone smiles. Heads shake in amused disdain.

Please Note: This article was accurate at the time of publication. When planning a trip, please confirm details by directly contacting any company or establishment you intend to visit.

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