To a 6-year-old boy, a 28-foot catboat must seem like the RMS Queen Elizabeth II, a vast ocean liner brimming with possibility and adventure. A child could wander all about the vessel, climb around the foredeck, lie down beside the boom using the sail as a hammock, explore the cavernous cabin down below, dangle legs from the stern, or nap in the spacious cockpit. Even with his parents and two brothers aboard, the vessel would feel homey and expansive. And for 6-year-old Kurt Peterson, his family’s catboat, Molly Rose, loomed in Cotuit Harbor as one of the largest boats of any kind in his little world. With her full sail pulled all the way up to its peak, she could practically eclipse the other boats sailing between Bluff Point and the Audubon sanctuary of Sampson’s Island. Anchored on the sandbars, she appeared almost as an island unto herself, or at least the tender to an island. Cotuit Bay, with its inlets and anchorages, is idyllic for day sailing, but from such a large, wide boat, it would appear small. A child on the decks of Molly Rose might imagine that he could reach out and touch the beaches on any side at any time. Sailing here could feel magnificent, but it could also feel constrained, enclosed.

Imagine, then, what it felt like for this 6-year-old boy to sail forth beyond the point of Sampson’s Island, out into the unknown waters of Nantucket Sound. One propitious morning, Kurt’s family set sail from their mooring in Cotuit, bound for the distant shores of Martha’s Vineyard, a voyage of some 25 nautical miles. Under sail, Molly Rose followed the channel out around the point of Sampson’s and soon left the last of the moored boats and Loop Beach behind. Perhaps a flock of terns attacked the water’s surface over the flats off Oregon Beach and Popponesset—the fins of bluefish in a feeding frenzy slicing the waves like miniature sharks. Likely, the wind held until somewhere out in the middle of the Sound, out beyond the chop of Succonesset Shoal. Here, with the land only a distant mirage to the West, with the Vineyard drawing into closer focus to the South, Molly Rose would roll against the current, and it would feel to the children aboard like the doldrums feel to sailors in the Inter Tropical Convergence Zone—dead. The suspense and the stillness would grow unbearable after the ease of sailing to this point, until finally, up ahead, the water would darken in the telltale ripples of a fresh seabreeze, and the big catboat would again make steady headway.

Where the Vineyard had loomed for hours as a light blue silhouette rising from the sea, it would begin to take on shapes and colors as the Molly Rose drew closer. The prevailing southwest breeze would cause the big cat to heel over; the boys might alternate from sitting on the rail like grown-up crew members to daring each other to sit down on the tippy side, where the water rushed past, inches from their faces. Over the windward side of the boat, the houses of East Chop and Oak Bluffs would come into focus, then Edgartown Beach would unfold. Well off the port bow, the sands of Cape Pogue would arise, along with the lighthouse. To the boys, this would resemble Sampson’s Island, but on a scale so massive that it would appear like another country. And then eventually, their father Eric Peterson would tack Molly Rose and sail Kurt and his brothers past Edgartown Light and up the channel into an enchanted sailor’s kingdom. Sure, 6-year-old Kurt had seen other sailboats before, but now he sailed past schooners that dwarfed Molly Rose. Along the wharfs and on the hillsides, shops and the mansions of ship captains sang to him. Later in the day, Kurt would wander through the village, and his life would take on a new direction, a destiny. Edgartown had cast its spell. Decades later, Kurt Peterson would move here, and since 2015, he has made his living by sailing his own catboat around these waters with his company, Catboat Charters. “I specifically remember as a 6-year-old walking around Edgartown,” he says. “Ever since then, it’s been my dream to make this place my home.” 

In recent years, a colloquial response to the question, “How’s it going?” is the answer, “Living the dream,” but most often, the line carries a hint of irony. Kurt Peterson, however, is one of those rare souls for whom the expression is literally true. When he recalls his childhood, he speaks fondly of “growing up on a catboat.” He has sailed all of his life, and in addition to cruising from Cotuit to Edgartown, his father took the family to Boston, Cuttyhunk, Nantucket, and Mystic, Connecticut. As an adult, Kurt has sailed from Maine to Key West; prior to founding Catboat Charters, he worked as a private captain, and he maintains a USCG 50-ton license with an Auxiliary Sail endorsement. Despite his wanderings, Kurt’s dream led him to open up his charter business back in Edgartown. In describing his son’s voyage to this point, Eric Peterson states: “Kurt and his three brothers all loved to sail from an early age, but I don’t think any of us thought you could actually make a living sailing. Pretty darn smart!” Success in the business did take a bit of time, however. Kurt recalls: “When I first started in 2015, I lived on the boat, a 24-foot Atlantic City Cat, until I really got things going. Now I have a place on the island.”

Kurt purchased his company’s flagship, Tigress, in 2016. Originally built in Wareham, MA in 1927, she had been lovingly restored by her previous owner, Roger Fuller. Kurt says, “All the wood is still solid, which is rare for a big boat of her age.” Tigress is 29 feet in length, weighs 22,000 pounds, and comfortably accommodates six guests in addition to the captain and his one-person crew. “She’s a real relic of a catboat,” says Kurt. “I’m really proud to own the Tigress.” Catboats are suited to day sailing charters since they are so beamy and stable; they don’t tip as much as sleeker sailboats, and with just one massive sail, they are far easier to crew than schooners or even sloops. Also, their sails typically carry at least two rows of reef points, which allow for decreasing the sail area on windy days. They are great boats for the Cape and Islands because they typically have shallow drafts. As Kurt puts it, “We can sail close to shore and see a lot of beautiful scenery that some other boats don’t have access to.” Many cats have interesting histories and personalities, as well, and the Catboat Association, of which Eric Peterson is a former president, is quite active in providing historical information and community news to boat owners and enthusiasts. One family that owned Tigress in her early years had sailed to Florida as a family of five, but by the time they sailed back north, they had added a new fourth child. “Last summer, some of the family members came out sailing with me,” Kurt recounts. “The mother was 90, the same age as Tigress. When she came aboard, she said, ‘Hello, old friend.’ It was so nice to see someone with such a connection to the boat.”    

Visitors to Edgartown’s waters will have little trouble spotting Tigress because of her unique sail, an American flag with all 50 stars and 13 stripes. Kurt and some friends painted this by hand using oil-based paint with added pigment powder and additional linseed oil so that it would soak deep into the fibers. The inspiration for the sail came from a photo of a cat named Cleopatra. “She sailed in the mid-late 1800s,” says Kurt. “Her flag sail was a celebration of reunification following the end of the Civil War. I adopted the idea because it’s such a positive message of unity.” This summer, Tigress will still fly a flag sail, but it’s a brand new one that Kurt helped build during his off-season job at Squeteague Sailmakers in Pocasset. In contrast to the old sail, Kurt says, “from the earliest design stages, we knew this would look like the flag, so it should be an improvement over the painted one.” Fittingly, this Memorial Day weekend, Kurt would hoist the new sail for the first time, for his first charter of 2019.

Memorial Day weekend marks the beginning of the summer season for Catboat Charters, and Captain Kurt will conduct up to four sails a day over the course of nearly five months. Crew members Haleigh and Carly will be working full-time again this year. A typical sail lasts for about two hours and takes guests around Edgartown Harbor, Katama Bay, the oyster farms, a view of South Beach, then out past Edgartown Light and along Chappaquiddick. Kurt says, “Sometimes if the wind is really light, we’ll skip Katama Bay and go all the way out to Cape Pogue instead.” Kurt is most grateful that the island has welcomed him into the business community. “They’ve really embraced Tigress,” he says. “Some people like to say they are self-made, but it’s really important for me to show gratitude to others who have aided in my success. I’m really thankful for the support of the entire community, including folks who just come over for day trips. If not for the time I spent exploring the Cape and Islands with my family, I would not be the same person I am today. If not for growing up on the water and having a dad who loved to sail, I might never have found this passion.”