Dream Flights

On April 3, Marco Island Executive Airport was the site of a dream.  

A couple of dreams, actually. Two military veterans, both in their upper 90s, took to the air in a 1945 Stearman biplane through the Dream Flights program, which was created for the purpose of giving these senior retired military personnel the chance to fly like a 1940s barnstormer in an open cockpit with the wind in their face. 

First to take to the air was Rudolph “Rudy” Billing. The 97-year-old member of the Greatest Generation is a World War II veteran of the United States Navy. 

Like Billing, the Stearman biplane is a World War II vet, with thousands of them having been manufactured to work as trainers for the fledgling Army Air Corps as it trained pilots and aircrew to fly and fight in the European and Pacific theaters. The Naples Municipal Airport got its start serving as a military training field during “the big one,” so it’s even possible that the Stearman flown from Marco Executive had previous flight hours in Southwest Florida.  

Speaking of flying hours, Dream Flights pilot Molly Littlefield has a long history with the Stearman airplane. She learned to fly on the Stearman belonging to her father, who was himself a World War II flight instructor. Molly went on to have a long career as an airline pilot, flying jets up to and including the Boeing 747, but her heart belongs to the biplane.  

Molly’s husband, Keith, also a pilot, serves as her crew chief, and at their home in a residential airpark outside Seattle, the couple owns a Stearman of their own, as well as a Super Cub and two Cessnas. They taught their son to fly on the Stearman.  

Rudy Billing was thrilled to take his “bucket list” flight on Wednesday morning. Getting the nonagenarians up into the front cockpit of the biplane was the most challenging part of the operation – along with getting them back down to terra firma after their flight – and Rudy started from a wheelchair. The Littlefields eased him into his seat, and Molly gave him a quick briefing before they taxied out to the runway – passing about a billion dollars’ worth of modern aircraft.  

“These are my rudder pedals. Keep your feet clear,” she said, pointing down in the cockpit and making it clear she would do the actual piloting that morning. 

They had to wait while a private jet came in for a landing on the airport’s sole runway, but then took off and flew circles over the golf courses and mangrove swamps surrounding the airfield. No one saw fit to point out to the fliers about the nest of crocodiles that live in the water just past the end of the runway.  

After the flight, Billing received a certificate documenting his flight, along with a Dream Flights cap signed by his flight instructor. He gave a “thumbs up” in return and asked how it was, said simply “great” before going into the terminal to rest up after his exertions.  

Paul McCarragher, 96, was the next copilot to fly. A veteran of the U.S. Army in Germany just after World War II, he worked calibrating instruments and enjoyed doing engine maintenance.  

“I just enjoyed the plane itself,” he said after his flight. Paul’s daughter and son-in-law, Joan and Jim Krzykowski of Naples were on hand to see Paul soar into the air.  

“It makes him feel very special they’re honoring him as a vet,” said Joan. “It’s been so many years since he served.”  

A third veteran, 87-year-old Armand Gaudiosi, an Air Force veteran who participated in Desert and Desert Storm, was also on the tarmac hoping to fly, but when his turn came, the climb up into the cockpit was just too much, and the team was forced to abort the flight for safety’s sake. He was looking forward to the flight. 

“I love flying. I’ve done multiple flights – everything from an A-1 Skyraider to a C-130 (the enormous military transport plane),” said Gaudiosi.  

All of the veterans selected for the Dream Flights are residents of Barrington Terrace assisted living facility in Naples, which coordinated with Dream Flights. Over 6,400 veterans have gone flying with Dream Flights since the program began in 2011.