What It’s Like to Be a Helicopter Tour Pilot

Every day, Tuckamore Aviation pilot Jeff Hubbard has the best seat in the house to watch the sun set over Boston. / Photo by Lloyd Mallison

Jeff Hubbard thinks he watched Top Gun too many times growing up. That’s how he says he got into aviation. Now, Hubbard spends his days cruising around Boston in a bright red helicopter.

The 34-year-old pilot helps run Tuckamore Aviation, a helicopter company based in Norwood that offers tours of Boston, the New England coast, and the surrounding area.

“We do enough different things that it’s pretty satisfying,” he says of flying Hover Boston, the company’s doors-off helicopter tour service. “There’s the beautiful city, a stunning harbor, other times we’re flying up into the mountains. There’s a mix of everything, which is pretty rare. It’s not Alaska, but it’s a nice spot.”

Hubbard has flown all over the U.S.—including Alaska (more on that later)—but is a local boy who grew up in Belmont…which is where he spent a lot of time watching Top Gun.

“I grew up wanting to fly,” Hubbard says. “I started going the airplane route, flying jets and all that, but I didn’t love it.”

He took some time off flying, despite knowing he wanted to stay in aviation, but took an intro class to helicopter flying on a whim, and was enthralled. “It was much more hands on,” he says.

“The two most intriguing places I’ve flown were Alaska and New York,” he says. “[New York] is a metropolis of massive buildings, lots of helicopters, lots of airspace. A lot going on. But seeing the pure number of buildings stacked on Manhattan from the air is pretty awe inspiring.”

Versus in Alaska, where there are definitely less buildings.

“Alaska is precisely the opposite,” Hubbard says. “Once you get out of town, there’s nothing but mountains, valleys, glaciers, and open space. You’ve really got to plan your route, because you can’t just land and hope there’s a place to refuel.”

Conversely, he says the most difficult things about flying in Boston are the temporary flight restrictions.

“There’s a three-mile radius no-fly zone for Red Sox games and Harvard football games,” he says. In a tightly packed city like Boston, that doesn’t let you see much of it.

That, and scheduling.

“Whether it’s not flying enough, or getting groups of four together to fly, it can be pretty tough,” he says. “There’s a lot of combining of groups, but the people are awesome.”

Hubbard had to pass plenty of certification levels, or “ratings” in helicopter-speak, to get his commercial pilot’s license and to fly the photo tours he does.

“I took my time over the years,” he says. “I did it bit by bit, rather than take out an educational loan, like one you put toward college, but for flying.”

He says the process involves increasingly scary steps, from getting comfortable in the cockpit and learning to hover—“It’s much more sensitive than people think,” he says—to instrument training, communicating with other aircraft, and planning routes.

“You can’t just be that guy taking it out on a Saturday afternoon in beautiful weather,” he says.

Hubbard was flying around the country in 2014 when he was approached to help start a helicopter company in Boston by a former student of his, a Wentworth Institute of Technology engineering professor. The two spent a year searching for the right helicopter and getting all the necessary approvals to run doors-off tours of the city.

He currently runs the operations side of the company and flies both doors-off photo tours and charter flights for the company. He says the latter is the more nerve wracking of the two.

“There are more variables: the weather, the locations of pick up and drop off,” he says of charter flights. “You’re either waiting for hours, or constrained as you’re on such a tight schedule. But you’re meeting different people, and going different places. It’s more involved, and that’s the fun of it.”

Hubbard is always ready for anything in the air, but he says some of the bigger surprises he’s encountered on the job have come before the chopper even left the ground.

“There was a group in their mid-70s who’d booked a doors-off tour, and I thought they’d made a mistake,” Hubbard says. “But they were like, ‘Screw you, we went skydiving last month, we want the doors off!’ We have huge guys scared to get into the helicopter and 75-year-olds ready to jump out of the thing.”

Unpredictability is part of the job, and everything is different for each flight, he says, from the people, to the weather, to the route, and even the aircraft. Some things are consistent though.

“You’re always a little anxious,” he says of flying the chopper. “But I still get that same rush in the air. I get the same excitement.”

Photo by Lloyd Mallison

Flying above Fenway Park, the rest of the city’s geography and icons are visible in a new way.

Photo by Lloyd Mallison

Hubbard uses the helicopter’s cyclic stick in his right hand, and an iPad to navigate around the Boston area.

Photo by Lloyd Mallison

Hubbard’s bright red helicopter is almost as conspicuous as his bright orange handlebar mustache. “Coming from Alaska with a beard,” he says, “I thought this qualified as a more professional look.”

Photo by Lloyd Mallison

In a city, Hubbard says, you’re looking out for everyone else, but flying in a rural area, you’re looking out for yourself. “There’s no place to fuel up,” he says. “Plenty of places to land, though.”

Photo by Lloyd Mallison

“Helicopters are awesome enough, but flying around with the doors off is a different feeling,” Hubbard says. “It’s pretty exhilarating. Pretty thrilling. Yeah it’s windy, yeah it’s cold, but…” But just look at the view.

Photo by Lloyd Mallison

Jeff Hubbard walks from the company’s hangar at the Norwood Memorial Airport to the tarmac where the chopper is parked, with all the swag of the Top Gun pilot he dreamed of being.

Photo by Lloyd Mallison

Hubbard’s helicopter sits on its helipad, ready to take off for a sunset tour.

Photo by Lloyd Mallison

The Prudential.