Taking the Wheel

Sometimes one person’s story can seem to contain the whole of human experience—tragedy and triumph, despair and resilience, dreams dashed and dreams made real. And sometimes it is hidden right in front of us. On this afternoon late last summer, the passengers who board the Volsunga IV for a leisurely 45-minute tour of the Thimble Islands will hear about the history, lore, and legends that have grown up around these bits of land in Long Island Sound, just offshore from Stony Creek, Connecticut. What they won’t hear from the captain is her own story, one that is as enduring in its own right: a story about a father, a daughter, and a village of boat captains who kept a promise.

On this day, as Anna Milne, captain of the Volsunga, slowly motors away from the dock to thread her way through the most densely packed group of islands in New England, it is 76 degrees, cloudy, almost dead low tide—a tricky time to navigate, with sandbars, boulders, and chunks of rock that jut above the water like massive turtle heads. She is 26 years old. Her captain’s outfit is a black blouse, yellow skirt, and sandals. She wears her long brown hair in braids. Her arms carry multiple bracelets, and her toenails are painted blue. A headset microphone allows her to save her voice and still have her narration carry throughout the boat.

Anna was born a “Creeker,” and her earliest memories are of sitting by her father’s side as he piloted the Volsunga. A lifelong Creeker himself, Bob Milne was known all along the Connecticut shoreline simply as Captain Bob. For a time he ran both his tourist cruise boat and the ferry for Thimble Island residents, before selling the latter in 2002. When he started his tours in 1987, he was 26, and for years he kept a journal filled with his observations and local knowledge. In 2005, after leading an estimated 12,000-plus trips, he published Thimble Islands Storybook: A Captain’s View. He wanted his family to know the islands the way he did.

“In my memory,” Anna told me, “it seems I was on the boat with him every day, all day.” And even when she wasn’t onboard the Volsunga, young Anna would trail after it in her own small craft, noticing where the rocks lay at high tide, learning the currents and how the wind shifted. (Being a Creeker, Anna told me, means that “you can be 7 or 8 years old and get in your Whaler with the little motor, and nobody bats an eye.”)

Over and over, Anna heard the island legends, her father’s anecdotes, with his pauses, his inflections, the way he drew word pictures, his voice rising and falling for emphasis. She understood that the stories he told were not just to entertain, but to bring the islands to life. The Thimbles would simply be masses of glacier rock to anyone who didn’t know about the families who once lived there or the laborers who cut the islands’ famed pink granite—stone so valued it helped build the Lincoln Memorial and Grant’s Tomb and the base of the Statue of Liberty.

On today’s tour, Anna motors the boat slowly past the Thimbles’ neighborhoods. About two dozen islands hold summer homes, and these are the ones that people come to see. Many of the residents have considerable wealth, and some are famous, yet most opt to live a rustic life: kerosene lanterns, outdoor showers, a quietude they can enjoy only 90 miles from New York City. Anna tells her passengers that Stony Creek and the Thimbles were once considered the “Newport of Connecticut,” with hotels and ballrooms; they were popular enough that President William Taft, who had become enamored with the Thimbles while at Yale, set up a summer White House on Davis Island.

When the Volsunga approaches Cut-in-Two Island, its passengers hear about “a small woman who lived here, Miss Emily,” and the famous small man who courted her: General Tom Thumb, of P.T. Barnum renown. “He was smitten,” Anna says, “and carved his initials on the kitchen door while declaring his love.” She pauses. “Then he found another and left Emily forsaken.” She pauses again, calling up the words her father said thousands of times. “Just like a man,” she says, her voice dropping for emphasis. “The scalawag.”

As the boat turns toward Stony Creek, it passes by Jepson Island. Here, Anna’s tone shifts. She tells about the Hurricane of ’38, which without warning battered the Thimbles, huge waves sending cottages into the sea, and seven lives lost. The passengers grow quiet, attentive, as she recounts how one family on Frisbee Island sought safety on the second floor of their home. The father gathered up anything that might float and tied it all to a mattress, which he implored his daughter to hold on to, no matter what. When the family was swept into the sea, only the child, her arms wrapped around the mattress, washed ashore alive.

I am a passenger on this afternoon tour, and when Anna Milne tells us about the hurricane I think about something she told me earlier, when I first met her that morning. She had been two weeks away from college graduation—her life course set for either law school or a graduate degree in history—and was attending a wedding, when a friend asked her to come outside. He had just received a phone call. “Sometimes,” Anna told me, “life just hits hard.”

Nobody knows exactly what caused the accident that changed everything. Bob Milne was the only one who could say, and afterward, he would never be able to. It happened on Saturday, May 2, 2015, a week into the new tour season. Just a year earlier, this magazine had featured a profile of Captain Bob. In the photo he stands tall and proud on the stern of the Volsunga IV against the backdrop of the Sound and the islands.

After Saturday’s tours were over, Milne and Mike Infantino, his friend from childhood and the captain of Stony Creek’s other 48-passenger tour boat, the Sea Mist, met up at the end of the day. Infantino told me he remembers Milne joking, “When is summer over?”

Later that night, Milne was riding his scooter on Gould Lane in Branford, a well-lit residential street close to Route 1. The night was clear, about 50 degrees. A truck was stopped at a red light, and for some unknown reason, Milne’s scooter collided with the back of it. He was not wearing a helmet.

When the emergency crews reached the scene, they knew how dire it was. The captain of the fire department called Infantino, who was a volunteer firefighter. “They told me he lost a lot of fluid and he might not recover,” Infantino said.

There would be weeks, then months, to come to terms with the limitations of medicine to restore Milne to a semblance of who he was. But Infantino knew what he had to do first. “The Volsunga will do her tours tomorrow,” he promised the Milne family.

A decade older than Milne, Infantino had seen him grow up in Stony Creek just as he himself had, drawn to the sea. Their boats had competed for the same passengers, summer after summer, for more than 30 years. Sometimes, they had words. “Your competitor is three feet away at the dock,” Infantino said. “Maybe you have an issue with each other: ‘You left too late,’ or ‘You came back too early.’ Or ‘That was supposed to be my group and they got on your boat.’” But, he added, “we always apologized to each other and always before the end of the day.”

Infantino knew every licensed boat captain in the area, his two sons among them, and they knew him. Eight of them came together and agreed to run Milne’s tours until season’s end in October. When Infantino piloted the Volsunga, someone else handled his Sea Mist. Former railroad signalman Bob Lillquist, hoping to ease into semi-retirement as ferryboat pilot, came on four days a week, and Anna joined the tours to tell passengers the stories she had grown up hearing. Infantino’s administrative assistant, Laura Missett, took on all the office work for both tour companies. The captains put family life on hold, and days off from other jobs became time spent piloting the Volsunga. Passenger fees were put in a separate envelope for Anna; when she tried to pay the captains, they refused.

Meanwhile, Milne was in the ICU at Yale–New Haven Hospital. “In the movies,” Anna said, “you are there when he opens his eyes. It wasn’t like that. It’s not like the movies. We thought maybe he’d be able to come back. We just didn’t know.” After six weeks, her father was moved to a rehabilitation center that specialized in traumatic brain injuries. He could not speak, walk, or eat, and gained his nourishment only via a feeding tube. Eventually he was moved to a nursing home. Sometimes Anna felt he knew who she was, other times not. Lifelong friends like Mike Infantino felt bad when they did not visit, and worse when they did.

Anna found a degree of solace in joining the captains aboard her father’s boat. She knew the narration by heart. As the captains navigated the Sound, she began to tell about the once-abundant thimbleberries that had given the islands their name, and how an excited scuba diver had brought what he thought was a pirate’s cannonball to the surface only to find it was a ball from a long-ago bowling alley on one of the islands. She found a YouTube video of her father’s tour, and she perfected the nuances, the tricks of rapport. Each day, she gained more confidence that she could hold her own with passengers.

When the season ended, the captains, along with Anna’s mother, Beth, and Laura Missett, had done all they could to keep the business alive. Now it was up to Anna to take the next step. “I knew I had to go to SeaSchool,” Anna said, “knew I had to learn to run the boat.” For her, there would be neither law school nor graduate school.

In the winter of 2016, Anna enrolled in two months of intensive, all-day classes at the SeaSchool in Freeport, Long Island. She studied everything from navigation and rules of the road to deckhand procedures. The instructor told her there had never been a female student in class before.

In May 2016, Anna started a GoFundMe page to buy the Volsunga from the family estate. More than 150 people combined to contribute nearly $14,000, and that season the boat became Anna’s.

The Stony Creek captains were again ready to not only pilot the Volsunga, but also to mentor Anna, to give her the confidence to one day truly be a captain. Bob Lillquist encouraged her to take the helm while doing the narration, as he stood by to maneuver through difficult areas and to dock. “Anna had to get comfortable behind the wheel,” he said. “It’s real tricky with reefs and rocks that you can’t see at high tide. These are among the hardest waters to navigate on the Sound.”

For her part, Anna said Lillquist became a crucial part of her new career journey. “Bob has always been in my life. [Before,] I didn’t know how important he was. He became my new Captain Bob.”

Anna had spent hundreds of hours on Long Island Sound, but the responsibility was different now, the stakes much higher. “I was hesitant,” she said. “You put nearly 50 people in this boat, and their lives are in your hands. I had never thought about that before. My dad just did it.”

When the 2017 tour season began, Lillquist stayed by Anna’s side. Then, one day in mid-June, a group of international students from Yale booked a special trip on the Volsunga—and none of the captains could get away to help Anna.

“I had been training for these years and everyone knew I was ready, but I was still nervous to go alone,” Anna told me. “My mom came on as my first mate, which made me both more comfortable and more nervous. She asked me if I was ready for her to [cast off]. I just took a deep breath and said, ‘Let’s do it.’ The trip went fine, and when I got back to the dock I told Bob that he could take the rest of the summer off.

“I would have continued to tell myself I wasn’t ready if it wasn’t for that one trip. I just had to get over that initial fear…. But after that trip, I thought, ‘I know how to handle this.’”

A few weeks after I took Anna’s Thimble Islands tour and met with Mike Infantino and Bob Lillquist—who both declared their pride in watching Anna’s seamanship abilities grow—her father was taken from his nursing home to the hospital. Anna was out on her final tour for Saturday, September 8. She was steering the boat past the island where Captain Kidd had his hideout, when the phone rang with the news: Her father was failing. He died the next day, his family by the bedside.

In a way, Anna told me, it felt as though she had her father back for the first time since his accident. She imagined him now being able to finally see her at the helm, his beloved Volsunga safe in her hands. Shortly after he died, she said, it rained and then the sun came out. “There was a rainbow,” she said, “and it started at my childhood home and ended at his childhood home.” She took a photograph of it, which she keeps on her phone.

A few days after that, on a day of rain with no passengers, she took the Volsunga out alone because, she told me, “the boat lost him too.” Then she steered back to Stony Creek, where Captain Bob had ended his workdays for so many years, and tied up to the dock with the knots he had taught her.

“It may sound silly,” she said, “but I feel like the boat and I finally know each other. She trusts me and I trust her, and we listen to each other.”