I have a healthy fear of flying and have made my phobia known to Carter Crabbe before climbing into his Cessna 172. Crabbe’s robust Southern drawl is as wide and winding as the Rappahannock River he grew up on, and his words are welcome reassurance: “I’m in there with you. I want to get back down on the ground, too.”

The vibe at Accomack Airport, a small municipal airport built during World War II in Melfa, Va., is casual and low key on this gorgeous summer morning. The sun hangs high in a blue sky dotted with cottonball clouds. With more than forty years of flying experience, Crabbe, a self-described “country boy” who was raised on a dairy farm in Morattico, Va., fits in well—his tanned skin, shorts and button-down short-sleeve shirt complement his easygoing manner.

Crabbe, sixty-two, is pilot and proprietor of W. Carter Crabbe Aviation, an umbrella company for his aerial spraying business, Car-An Flying Service (named in part for his wife, Anne), and his charter and sight-seeing venture, Chesapeake Aviation. When he’s not dodging power lines and buzzing over farmland spraying crops, Crabbe is flying people—everyone from business people to Senator John Kerry, and, recently, rock legend Robert Plant of Led Zeppelin—”just coming and going” up and down the East Coast. Crabbe’s sightseeing tours provide passengers a unique bird’s-eye view of Virginia’s Eastern Shore.

Before we embark on our hour-long excursion, I’m introduced to Newton Lee, Crabbe’s six-year-old basset hound and occasional co-pilot. “The dog’s the boss,” says Wallace Bailey, Crabbe’s long time flight assistant.

Crabbe agrees. “People ask me if that’s my dog. I say, ‘No, I’m his.’”

As we taxi to the runway, Crabbe asks, “Want a piece of gum? That’s all I’ve got to offer.” There’s no in-flight service, no peanuts, no beverages. What you do get is much more thrilling and satisfying—the chance to witness, first-hand, a pilot, instruments and controls at work.

Crabbe hits the throttle, and we lift off. My preflight fear has been replaced with awe as I watch our plane’s shadow sweep over thick groves of pine. We level out at a cruising altitude of approximately 750 feet and head northwest toward the Bay where the coastline looks like carved teeth on a house key. Over the roar of the single-prop engine, Crabbe points out Tangier Island, a destination to which he frequently flies passengers to and from.

As we pass over the deep-water harbor town of Onancock, streets, churches, and homes appear like pieces on a model railroad set. The railroad track running parallel to Route 13 resembles a zipper cutting through quilt-like patches of corn, soy beans, and tomato fields. Creeks and rivers curve like snakes east and west, spilling out into larger bodies of water.

Crabbe hears that a lot—the perception of size up here in the wild blue yonder. “I have flown people who have lived here all their lives, and the first thing they say is, ‘Look how small it is.’ Everyone says it looks like Matchbox toys.”

We reach the Atlantic, and Crabbe guides the airplane south along Cedar and Parramore islands, two of Virginia’s sixty miles worth of barrier islands that hug the coast. Down below, sand mixes with mint green water, which turns blue as the ocean extends east away from land. Fishing boats bob up and down and porpoises spring from the water. Weather-beaten beach houses stand on stilts. As we turn inland, the remains of an old shipwreck are visible on Parramore Beach; Crabbe circles, and we make a small, yet exhilarating, dive to get a closer look.

“There’s no other way to see it,” Crabbe says, referring to our particular view of the Eastern Shore. “If you are driving, you can’t get to half of the beaches or to some of the pretty homes on the creeks. If you want to see nature or the houses or whatever, you just can’t see them, and in your boat you can see some, but you can’t see it all. I think the only way to get the true perspective is to fly over it.”

Landing, you get the feeling you’ve been on a roller coaster ride that ended too soon. Back on terra firma, I ask Crabbe if he’s had any close calls.

“My flying career has been very uneventful, and that’s the way I want it. People ask me, ‘How many times have you crashed’ and all that stuff.’ You’re not supposed to be doing that.” I take his meaning as: number one, not crashing, and number two, not asking that question in the first place.

Crabbe does remember, however, hitting some nasty weather on a flight from Tangier a few years back. A passenger turned to Crabbe and asked, “You ever seen it this bad before?”

Crabbe: Yeah.

Passenger: You ever seen it any worse?

Crabbe: No.

Passenger: I wish you hadn’t told me that. 

Crabbe: Well, you asked.

During the summer months, between spraying and charters, Crabbe will fly from 5 a.m. till 9 p.m. Despite the long hours, after all these years, Crabbe still enjoys climbing into the cockpit. “When I get tired and disgusted, I look down and I don’t see anybody down there doing anything I want to do, so I keep on plugging away.” With a smile, he adds, “I certainly do enjoy the view.”

While not “Top Gun” material yet, freelance writer Jason Tinney has a new appreciation for flight.

W. Carter Crabbe Aviation and the Charlotte Hotel & Restaurant in Onancock have teamed up to offer a “Fly & Stay” package, which includes a one-hour sightseeing flight over the Eastern Shore/Chesapeake Bay, one night’s stay, and a three-course dinner for two (including one glass of wine per person) at the Charlotte. $495 for two. 757-787-7400, http://www.thecharlottehotel.com. Sightseeing tours only are $275 per hour for up to three passengers. For more information about tours and charter flights, contact W. Carter Crabbe Aviation, 757-787-2901.