come fly with us

Crabbe Aviation

From 2000 feet view the natural beauty of the Eastern Shore, historic Tangier Island, Wallops Island Space Center, and the unspoiled, uninhabited barrier island beaches that line the Shore from Maryland to the mouth of the Chesapeake Bay.

Chesapeake Aviation, Inc. has been in business for 45 years. Our FAA approved, 4-place aircraft is flown by our professional pilot, W. Carter Crabbe. Carter has many years of experience doing sightseeing trips from the sky and air taxi-charter flights to many different destinations.

Whether you want to explore the coastline, search for property, or get to a destination, Chesapeake Aviation can provide the professional service to meet your needs. Call us now to schedule your flight.


The Pilot

Carter Crabbe has been a pilot for 45 years, with over 30,000 hours of actual flying time. He has 45 years of crop dusting experience and is the only pilot licensed on the Eastern Shore to provide on-demand Charter flights. Over his flying career, Carter has been featured in many aviation magazines, local Eastern Shore Essentials magazine and newspaper articles. Carter is very passionate about flying and enjoys sharing stories about his flying career.

Carter is enthusiastic, professional and very knowledgeable about the Eastern Shore.

Federal Aviation Administration, FAR part 135 licensed, certified, inspected and insured to provide on-demand charters and air taxi services.

Member of the Eastern Shore Chamber of Commerce, Aircraft Owners and Pilots Association, Northeast Aerial Applicators Association, National Agriculture Aviation Association, Pungoteague Ruritans, and Craddockville United Methodist Church.


The Plane

Chesapeake Aviation, Inc. has two Cessna 172 Skyhawk airplanes. Both airplanes go through periodic inspections to meet the safety requirements put forth by the FAA.


Sight-Seeing Flights

Take a 30 minute or more sightseeing flight in our FAA approved 4-place aircraft, flown by our professional pilot.

Enjoy breathtaking views of both the Chesapeake Bay and the Atlantic Ocean as you fly above Virginia’s and Maryland’s beautiful Eastern Shore. Bring your camera!

See Assateague Island, home of the wild ponies, Tangier Island, located in the Chesapeake Bay, Wallops Island, home of the NASA launch facilities, the Barrier Islands along the Atlantic Ocean just off of the small water front town of Wachapreague. You may want your trip to include a flight over the historic town of Onancock, your home, a friend’s home, or a property that you are interested in.

Up to 3 people can come aboard for a 30 minute or more flight. Extended flights are available.

Gift-certificates are available. A great gift for a birthday, anniversary, Christmas or any special occasion.

Contact us today to schedule your flight.


Charter Flights

Carter Crabbe is the only pilot licensed on the Eastern Shore to provide on-demand Charter flights. He is licensed to charter anywhere in the United States.

Trips to Tangier Island, Williamsburg, Norfolk, Richmond, Baltimore, New York, Carolinas and many others are all possible with Chesapeake Aviation, Inc. Need to get there and back without all the wait time in traffic? Go, stay as long as you like and know that you have a scheduled chartered trip home.

Take a chartered flight to your desired destination and see much more from the air.