Can elation come from elevation? In an age of TSA pat-downs that go further than most first dates, it’s refreshing to simply climb onto a plane in the sunny outdoors on a midsummer day. Even if the flight requires a parachute.

At the Katama Airfield, Classic Aviators offers flights ranging from 15 minutes to an hour and will take you anywhere on the Island. Whether you want an airborne view of Chappaquiddick and Edgartown or are yearning to see the Cliffs of Aquinnah from above, Mike Creato can fly you there.

Mr. Creato has been flying biplanes since 1994 when a friend got one and the two of them taught themselves how to fly it. “The grass runways are more forgiving,” the pilot said of his learning experience, as he landed one of the biplanes he owns with his friends and partners Don Lambert and Brian Hall. Asphalt would not have been so kind. He recalled that while he was learning to fly the plane his grandfather, Steve Gentle, who used to own and manage the airfield, left the field for five days, convinced that his grandson would wreck the biplane.

Today, 17 years later, Mr. Creato is still here and still flying. With 3,500 biplane hours and roughly 10,000 rides with passengers under his belt, he is a calm presence at the controls. The seating arrangement is counterintuitive — passengers sit up front and Mr. Creato sits behind them — but as the plane lifts off, thoughts that Mr. Creato couldn’t possibly see anything vanish in the wind whipping around a passenger’s leather helmet and goggles. Mr. Creato’s voice comes through the headphones. He’s a chatty and amiable tour guide, pointing out landmarks, boats and marine creatures.

For a first time passenger, it feels like you’re Amelia Earhart.

The high vantage point offers a unique view of the Vineyard. Norton Point, Harthaven harbor, Farm Pond, Chappaquiddick, Edgartown, Oak Bluffs and Vineyard Haven slide by beneath us. The traffic at the blinker intersection looks almost as bad from above as it feels from behind the wheel. The harbors are so full they look as if they couldn’t possibly hold an extra kayak, let alone a boat.

We’ve got a thousand feet between us and the hustle and bustle of summer on the Vineyard. Landmarks are points of familiarity on the real-life map spread out beneath us. The West Chop Light presides over its harbor. The wide expanse of Ocean Park appears so much smaller from the air. A line of cars hover behind a moped, waiting to pass.

Then it’s back to earth. “It’s a good weather operation,” Mr. Creato declared. He said overcast days bring the most business. “Fog is expensive to us,” he said.

One or two people can go up at a time.

And the Katama Airfield is a place unto itself, situated in the grassy, open plains of Katama, the roar of the ocean at South Beach a short stretch down the road. The airfield is a Class G airspace, which means no air traffic control tower, for one thing.

The radio at the airfield is manned by Jack Januszewski, a 17-year-old self-proclaimed aviation junkie and jack-of-all-trades who helps out with many tasks at the airfield. Oftentimes older planes that have no radio simply come in for a landing without announcing themselves, causing Mr. Januszewski to hop on the radio and warn any nearby aircraft. He grew up near the airfield. “I was just one of those kids that fell in love [with flying and the aviation world],” he said.

The airfield was purchased in 1983 from Mr. Gentle by the town and the state, and The Nature Conservancy holds a conservation restriction on the surrounding land. Rare beetles and flowers thrive out here alongside small planes of every description, including antique planes owned by aviation enthusiasts. Mr. Creato manages the airfield. Classic Aviators sits alongside The Right Fork diner and a glider tour business.

But back to the parachute. At Classic Aviators, all flights come with a thrill option that can include a barrel roll to something called a hammerhead, possibly better left unexplained. Federal Aviation Administration rules require passengers to wear parachutes as a precaution. But gravity keeps you in your seat rather than pulling you out of it, and there’s always the “Oh, Jesus!” bar to hold on to in those hair-raising moments.

And even if your stomach curls up into a little ball while your back is pressed to the seat during a loop, coming in for the landing you may find yourself wishing you could stay up for just a few minutes longer.