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Thimble Islands | Tour Connecticut's Vacation Retreat

Thimble Islands | Tour Connecticut’s Vacation Retreat
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Captain Bob Milne’s tours of Connecticut’s Thimble Islands are big on legend, lore, and history—but what he doesn’t tell you also reveals island truths.


Don't Miss Arrow Slide Show: Thimble Islands

Captain Bob is talking about rocks. Again.

Wearing a microphone headset and perched up in the bow of his 48-passenger tour boat, the Volsunga IV, Captain Bob points out the granite rocks of Cut-in-Two, then adds a critical detail: Tom Thumb carved his initials into those stones more than a century ago. The passengers murmur appreciatively; it’s a small, lulling sound, like waves against a hull. Then we pass Dogfish Rock, and Captain Bob points out that it’s one of the few manmade islands hereabouts—created by piling rock upon rock hauled from the mainland—and he uses this fact to launch into a brief disquisition into how owning an island could raise the status of members of the gentry during the late Victorian era. Near Bear Island, once home to an active quarry, he tells us that the island’s distinctive stone can be found today in the Lincoln Memorial, Grant’s Tomb, and the base of the Statue of Liberty. Lips purse into the universal “who knew?” expression, and heads nod.

Captain Bob is Bob Milne, a lifelong resident of Stony Creek, Connecticut. He’s the owner and operator of Thimble Island Cruises, leading 45-minute tours through these islands throughout the summer. It’s a little-known fact, but animating rocks is one of the skills honed by good tour guides. They can take something inert and uninteresting and inject a bit of wonder into it. They mine rocks for murmurs.

We motor on, and Captain Bob points out Governor Island, now populating it with one Mr. Weed, a businessman and avid gardener who lived there during the early decades of the last century. He paints a vision of a white-goateed gentleman puttering around the harbor in an elegant mahogany steam launch and wearing a white captain’s cap. “And the name of Mr. Weed’s boat was …?” Captain Bob trails off in a question. He awaits an answer, which isn’t forthcoming from the two dozen passengers this morning. “The Sea Weed, of course,” he says. A muffled groan arises, and Captain Bob waits for it to subside before adding, “If you’re overthinking it, you shouldn’t be on this boat.”

One of the most common descriptions of the Thimbles—an archipelago of some 100 to 300 islands (the number depending on the tide and your own definition of an island, as opposed to a rocky outcropping) just off Stony Creek—is that they look like a piece of Maine that somehow broke free and drifted south before running aground in Long Island Sound. That’s a hard description to improve upon. Like their granite cousins to the north, these islands are craggy and stoic and come in eclectic shapes and sizes—some round like igloos, some long like bony fingers.

Two dozen of them are capped with houses: some small; others that seem out of scale, like a large hat sitting precariously atop a head. Many were built as island getaways for the affluent, who arrived by steamship or train from New York, or by streetcar from New Haven, about a dozen miles to the west. The Thimble Islands—named after the thimbleberries that grew on them, not their diminutive size—didn’t attract top-tier robber barons, but rather their court followers, including bankers and brass-mill owners. “We were a notch below Newport,” Captain Bob says.

Captain Bob is nearing 54 years old and grew up on the mainland in Stony Creek, when it was still more or less a blue-collar working waterfront, a poor-cousin coastal neighborhood that’s technically part of the town of Branford. He was one of six kids; he stayed as his siblings all moved away.

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.

Please Note: This information 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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