Gliding across Edgartown harbor on summer afternoons is a gleaming wooden catboat equipped with an American flag sail. For many years, the famous sail was carried by the catboat Tigress, captained and chartered by Kurt Peterson. This summer, the sail is still blowing across the harbor — this time atop his catboat Dolphin.

Built in Wareham in 1927, the Tigress patriotically carried passengers through the harbor for a decade under Mr. Peterson’s care. Her stars-and-stripes sail, instantly recognizable, is under trademark — Vineyard Vines even released a line of shirts featuring it billowing from her mast.

Mr. Peterson still charters the Tigress on Nantucket, captained by his former first mate, Priscilla Stoll. The departure of the Tigress is making way for the Dolphin, adorned with the signature sail, to return to her harbor of origin. 

The Dolphin was built on Chappaquiddick in 1893 by George Huxford, a contemporary of the famed shipbuilder Manuel Swartz Roberts. She changed hands many times over the years, becoming detached from her Island roots. When Mr. Peterson acquired her, he jumped at the chance to restore her and bring her home.

The familiar stars and stripe sail is a beacon on the harbor. — Hailey McLaughlin

“It’s a special boat with a lot of history that’s pertinent to this area, so I thought it’d be great to have the Dolphin back here in Edgartown where she was built 130 years ago,” he said.

Mr. Peterson said that the newly-restored Dolphin is better equipped than the Tigress for his two-hour charter cruises through Middle Ground. The renovations have been extensive — he rebuilt and repositioned the bulkhead, gutted the cabin and expanded the cockpit to be 9 feet long and 12 feet wide. The changes are accommodating of bigger parties, but they’re also historically accurate.

“This is how it was originally set up when it was built in the 1800s,” he said, gesturing to the cockpit.

Mr. Peterson has spent the last decade chartering his catboats out of Edgartown harbor. He got his first taste of Vineyard life at four years old, when he and his father sailed into Edgartown harbor on his father’s 28-foot catboat, the Molly Rose. He earned his captain’s license in 2015, and he’s been chartering his beloved catboats while meeting clients from all over the world ever since.

“It’s a combination of my two favorite things,” he said.

Catboat fever runs in the family. His brother, Ryan Peterson, owns a catboat that he hopes to soon begin chartering out of Charleston, N.C.

The lure of the catboat is strong. — Hailey McLaughlin

Mr. Peterson’s first mate is Max Heredia, a rising sophomore at Lafayette College who has summered for six years on Chappaquiddick. Mr. Peterson said he wouldn’t trust just any sailor with his catboats. While most sailboats have multiple sails to aid in smooth navigation, catboats have just one large sail, which makes them particularly finicky.

“It can be kind of a bear to handle,” Mr. Peterson said. “You really have to know what you’re doing.”

Though catboats are now most often used for sunset pleasure cruises and elopements-at-sea, the sleek vessels were once the workman’s boat of choice, used for everything from fishing to transporting goods. Mr. Peterson says the Dolphin was originally used to ship lumber.

There’s plenty to see off the Dolphin’s bow, from the summer home of Walter Cronkite to pods of dolphins lapping at the boat’s hull. Wind and weather permitting, Mr. Peterson spends as much as eight hours per day at sea, showing patrons the sights and occasionally overseeing their biggest milestones. He once officiated a wedding aboard the Tigress.

“I hope we’ll have more of those moments on this boat,” he said while steering Dolphin through the harbor.

The Fourth of July is usually a busy day for Mr. Peterson, but due to high winds he tucked away Dolphin’s sail this Independence Day.

“I’m taking the day off for the first time in 10 years,” he said.