HYANNIS — For as long as he can remember, Dan Wolf has been a tinkerer — a fidgeter, a fixer and a figure-outer, happy to futz with anything he could get his hands on. When he was young, it was gas-powered model planes, connected to his fingers with a string as they puttered through the air. His dream was to fly one.

“I was that kid at the airport fence,” Mr. Wolf said in his office just outside the Boardman/Polando Airfield in Barnstable. “I was that way with birds. Anything that flew, I was just a nut about it.”

Nearly 60 years later, Mr. Wolf — a former three term state senator — is the CEO of Cape Air, the largest commuter airline in the country that offers service throughout capes and islands across the globe, from Martha’s Vineyard to Micronesia. He started the business in the late 1980s as both the pilot and the mechanic, flying the original Provincetown to Boston route himself, helping to maintain the planes, and, if the phone rang when he was in the office, scheduling the reservations. Last week, the company’s nearly 1,000 employees celebrated their 30th anniversary.

He’s been behind — or above — the airport fence for all of it.

“It’s been an amazing ride,” Mr. Wolf said. “And it continues to be.”

Now, 30 years after Mr. Wolf made his first flight in the nine-passenger Cessna 402, the company has a new ride. Cape Air received its initial order of Tecnam P2012 Travellers last week, the first custom-built, twin-engine aircraft made in the last quarter century. Over the next decade, the airline plans to replace its aging, 40-year-old fleet with the sleek Italian aircraft, hopefully one day priming itself to be the first airline flying entirely electric planes.

The airline also now offers year-round service from the Vineyard to New York city, and last December bought the largest sea plane manufacturer on the East Coast. Next summer, it will offer amphibious flights that take off from the Vineyard and land on 23rd street Manhattan in the East River.

Even for the man who is always tinkering, it feels like change is in the air. And nobody has a better view of it than Mr. Wolf.

“I’ve been a pilot for 42 years. Imagine the blessing I’ve had to fly over this,” he said, gesturing to the land below him. “And from a climate change perspective, it gives you a sense of how fragile it is, how connected it is . . . the thing I love about where we are now, is that we’ve got the new airplane, but that’s really a bridge to the electric airplane. Ultimately, it undoes the impact that we’re having, and that really excites me.”

He grew up in Philadelphia, the son of a colonial American historian and University of Pennsylvania professor, raised with both a deep appreciation for American patriotism and American liberalism. He lived in a Jewish household but attended a Quaker school, educated in the combined ethics of Tikkun Olam, the Jewish tradition of repairing the world, and Monthly Meeting, the Quaker tradition of cultivating intellectual curiosity and friendship through it. He became passionate about air travel and gender equality, interested in ensuring that women made 100 cents on the dollar and that he did too. He attended Wesleyan University for a liberal arts degree. He spent the next two years at a vocational college.

It’s why he is both political and pragmatic — a dreamer entrenched in reality, equally inclined to go on philosophical diatribes about the Democratic party’s moderate wing as he is to detail the technical repairs necessary to fix his Cessna’s left wing.

“I’m the only guy who left Wesleyan University with a political philosophy degree and then went to a two-year vocational school for aviation technicians,” Mr. Wolf said. “I’m the living contradiction.”

Over the past 30 years under his leadership, Cape Air has expanded from a boutique commuter airline into a still-growing international operation, sending its fleet of 102 airplanes from Cape Cod to the Caribbean and beyond every winter. While the airline’s first route was Provincetown to Boston, its second one was Martha’s Vineyard to Hyannis. The Island has always been integral to the business, its unique nine-passenger planes ubiquitous on the regional airport’s tarmac. One of Mr. Wolf’s favorite routes was the 33-minute Martha’s Vineyard-to-Boston journey, the perfect time integral to do one flight per hour.

“Back in the beginning, it was like, give me an airplane and I’ll just fly all day,” he said. “Book until you puke.”

Ten years ago, sensing that the 40-year-old Cessnas were on their last legs, Cape Air put out 30 RFPs for a new airplane. There were a few qualifications. The plane needed to be small and capable of doing short stage lengths, so it didn’t need to be pressurized. But it needed to have two, reciprocating fixed-gear engines in case one gave out. Nobody else in the world needed it. And nobody in the United States wanted to make it. That’s why Mr. Wolf went to Italy.

“It was Goldilocks and the three bears,” he said. “The manufacturers that were too small, they didn’t want to risk it. Too big, not worth it. For Tecnam, it was a sweet spot.”

Founded by two brothers in Capua, Italy, Tecnam, is one of the largest aeronautics manufacturers in the world. When Mr. Wolf arrived, it was clear they were the perfect design partner.

“We went over to Italy. We toured the plant. And we sat down, and we said, what would this look like? And they said, what do you want this to look like? And that was a great response,” he recalled.

Together, Cape Air and Tecnam built the P2012 Traveller. Whereas the Cessna 402’s cockpit is covered in steam gauges, gyroscopes and analog instruments, the Traveller’s is a television screen, high tech and covered in glass. It has modern navigation, communication and engine monitoring systems. Where the Cessna has ashtrays next to its seats, the Traveller has USB ports — and room for a carry-on bag underneath them. Flying Cape Air is always a unique experience, with its 1970s aesthetic and open windows. In Mr. Wolf’s view, the Traveller allows it to be a truly comfortable one, too. The new planes have air conditioning.

Three years ago, Mr. Wolf became the first American to fly the Tecnam.

“It’s an incredible airplane,” he said. “It’s a game-changer.”

It wasn’t always clear that the man with pie-in-the-sky ideas would end up back in it. In 2012, Mr. Wolf ran for and won a seat in the state senate, inspired by watching his three daughters come of age in a 21st century America where women still only made 82 cents on the dollar.

“It was not a change in careers. It was a response to a world where I think more people need to step up and contribute,” he said.

On Beacon Hill, Mr. Wolf became something of a progressive firebrand, championing universal healthcare and climate change initiatives. But he also remained CEO of Cape Air, and afte r three terms decided that it was too difficult to juggle the weekly commutes to Boston with the needs of his company. He launched a campaign for governor that got derailed amid ethics questions about MassDOT contracts with Cape Air. Although those were ultimately dismissed, it was too late for the campaign to continue.

It meant Dan Wolf got to return to a job he loved. He doesn’t know if he’ll return to the other one.

“To the degree that people like me have a voice and have an opportunity to make positive change, I think that responsibility is an obligation,” he said. “Which means that I probably won’t run for office, but if somebody asked me to serve in a position, if the government asks you to and you have the values that I have, you don’t say no. Especially during times of need. Maybe the last chapter is written, maybe it isn’t.”

Mr. Wolf just became a grandfather. He said the experience reminded him of the “fierce urgency of now.” He discovered there’s always more tinkering to be done.

“I’m 62,” Mr. Wolf said. “The responsible thing to do here is to make sure that the 30 years looking back, looks forward also. And so, right now, I’m spending a lot of time making sure . . . that this company has as bright a future as it has a past. And that’s really exciting work to be doing. I love doing it.”