Thimble Islands Cruise | Connecticut’s Vacation Retreat

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. “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. Later that day, back on the mainland, on Captain Bob’s recommendation I walked up the road to the new Stony Creek Museum, housed in a handsome former church near the train trestle. The exhibits include sepia-tinged photos of old marching bands and creaky-looking 19th-century seaside buildings with deep-set wrap-around porches. I learned that tourist traffic began in 1852, when the New Haven & New London Railroad started service here, and boomed in the late 19th century. The village population tripled, with many new residents catering to vacationers. And the museum dwells long and lovingly on the role of quarries, with intriguing black-and-white photos and examples of old tools. As I examined a large mallet, a no-nonsense woman in a pink blouse and wire-rim glasses walked over. “Quarry workers came from Sweden and England and Finland and Italy,” she told me, “and their descendants are still here.” She introduced herself as Judy Robison, chair of the board of the new museum and, I later learned, the small institution’s driving force. I told her I was curious about the islands, and she pointed out a weathered sign that read Bathers Please Be Quiet During the Church Service. It had come from Money Island, one of the more populated (and, actually, least wealthy) of the Thimbles. And, as it happened, that’s where she and her husband had lived summers for years, in a former small hotel they’d bought some time ago. “We have the grandkids out there—barefoot all summer and no television,” she told me. They cadge a little electricity from the sun via solar panels, but not much. “I can’t use a vacuum cleaner very often,” she said, “and that’s not a complaint.” She paused a moment and seemed to be gauging the depth of my curiosity. “You want to see an island?” she finally asked. About a half-hour and a short boat ride later, we were walking around Money Island, seeing where the bathers once threatened to distract churchgoers, and where an old phone booth now serves as the island’s library, piled with books for swapping. I’d noticed that Captain Bob sold “pirate maps” on board his boat for three dollars, but sitting on Robison’s porch with Judy, her husband, one of her kids, some grandkids, and a neighbor who had dropped by, I asked about another map I’d been given by my motel manager back in town. It was titled “Christine’s Islands.” When I mentioned it, they smiled, perhaps a bit tightly, then pointed out several islands between the porch and the mainland. Each of them had bright flags fluttering from three-armed nautical flagpoles. And all these islands were acquired, mostly in the past decade, by Christine Svenningsen, the widow of a man who’d made his fortune in a way that would have mystified the old railroad tycoons: He built an empire of party-supply stores. Svenningsen now owns 10 islands, including the jewel in the crown, Rogers—the one with the palm trees and greenhouse. She doesn’t give press interviews or talk about why she’s so fond of owning these islands, so a favored pastime among Islanders and Creekers alike is to speculate about what she’s up to and wonder why her islands often sit empty through the summer. Turns out there are more theories than islands, none very satisfying. While we talked, it struck me: Captain Bob had never mentioned Svenningsen on the tour. Paraphrasing poet Adrienne Rich, Jonathan R. Wynn, author of The Tour Guide, notes that “every point on the map is not just a place in history, but multiple points.” It’s a different point for an ecologist, a historian, a folklorist, or a summer person. Or for a tour guide, who has to navigate a treacherous course around not only rocks but also local sensibilities. A tour guide possesses an invisible map, filled with things that don’t get mentioned. Captain Bob doesn’t name names of the living; he has to stay on good terms with the residents. He confided to me that Garry Trudeau, the Doonesbury cartoonist and husband of broadcaster Jane Pauley, takes him aside early each summer and asks him not to point out his house on the tour. Captain Bob chuckles, because he wouldn’t do that anyway. It’s a small community, after all. But someday, years from now, another tour guide will pilot slowly through here and talk about a famous cartoonist who once lived here and worried about his privacy, and a wealthy widow who had the money to buy island after island. Passengers will smile and murmur. Captain Bob pilots us back into the harbor, and soon he’ll climb out and smoke one cigarette, then get ready for another group of passengers, and another 45 minutes of bringing rocks to life and keeping local ghosts alive. The dock comes into view, and Captain Bob clears his throat and enunciates more loudly and with more gravitas than he has the whole tour. “Next stop,” he says, “Stony Creek.”

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Thimble Islands | When You Go

Thimble Island boat tours run from May through October. Call tour operators for details, or visit the Web sites listed here. Captain Bob Milne on the Volsunga IV 203-481-3345; thimbleislands.com Captain Mike Infantino on the Sea Mist 203-488- 8905; thimbleislandcruise.com Captain Dave Kusterer on The Islander 352-978-1502; thimbleislander.net Stony Creek Museum 203-488-4014; stonycreekmuseum.com