A Pilot’s Guide to the Florida Keys

Fly out of Miami International Airport (KMIA) on a clear day, and airline pilots and their passengers catch a stunning view of the Florida Keys and, probably in most cases, wish they were there.

There are few places more intensely romanticized in popular culture than the Keys. Featured heavily in songs by musical artists from Jimmy Buffett to Zac Bryan, in films from Key Largo (1948) to True Lies (1994), and perhaps most of all in the writing of author Ernest Hemingway, the string of islands stretching for 120 miles off the tip of the Sunshine State have long occupied space near the top of travelers’ wish lists.

For private pilots, the magnetic pull is especially strong because of the state’s vibrant aviation culture and the warm, sunny weather that supports it. If you are flying your own aircraft to the Keys, which in our case is the recommended way to get there, the excitement rises notably as you approach Miami. Pretty much regardless of where you are traveling from, Miami serves as the gateway, funneling you along a scenic, fascinating path of islands, highway, and bridges that lead to Key West.

Key West’s location at the end of the archipelago is appropriate, as for many visitors it is the ultimate destination. There is, however, so much to see on the way that people driving from Miami often plan a day or two of travel with many stops along the way to take in as much local color as possible.

The succession of restaurants, gift shops, cafes and themed attractions, and the temptation to stop at every one can multiply the duration of what should be a four-hour drive from the mainland to Key West. Perhaps you already see the many advantages of flying. 

Aviation Gateway

Cruising at, say, 2,500 feet or even better, below 1,000 feet, you cannot just pull over every time you or your passengers spot something interesting. You could also cover the trip from Miami to Key West International Airport (KEYW) in a little over an hour by air in a high-performance piston single.

But what’s the hurry? There are so many resorts, beaches, and other potential stops along the way that you might want to combine the joy of flying with the ability to make stops almost anywhere. It may sound like a fantasy, but Nick Pontecorvo, owner of Keys Seaplanes, has been making it happen for decades.

Flying a 180 hp Cessna 172 on amphibious floats, Pontecorvo can pick up and drop off passengers at airports, waterfront resorts and homes, and many other spots that are otherwise accessible only by boat.

Clients can book a variety of sightseeing flights, and when they do, they are often pilots interested in an informal sampling of the seaplane experience.

“They drag the family along,” Pontecorvo said, with the pretext of a scenic tour but deep down they are thinking about getting a seaplane ratings.

Tours rarely crop up on his busy schedule, though, because most clients just want to get from the airport to their final destination—the “last mile”—as quickly as possible.

“That is 98 percent of my business,” he said.

Typically travelers arriving at Miami International meet him at the FBO—and away they go. This is especially significant because the remote rental car garage is a long walk away from the airline terminal and eats up a lot of time.

“Sometimes I can get people to the resort faster than they could pick up their rental car,”  Pontecorvo said. 

I do not think he was exaggerating. My wife, Alex, and I traveled to Islamorada in the Keys in March and noticed the unusually long hike to the rental desk.

If you fly to any of the smaller airports, in and around Miami, commercially or in your own aircraft, Pontecorvo will pick you up and deposit you on the beach at your resort, like a scene from a movie.

Speaking of movies, when flying low along the shore or over the Seven Mile Bridge, it is hard not to think of Timothy Dalton as James Bond in a helicopter pursuing the villains’ Cessna 172 over the Keys’ beaches in 1989’s License to Kill.

The long bridge, especially the old section, always reminds me of Arnold Schwarzenegger and a flight of Marine AV-8 Harriers blasting the span with missiles to thwart fleeing baddies in 1994’s True Lies.

Seaplane Solution

For Pontecorvo, who earned his private pilot certificate in 1991, between those two movies the path toward aviation and ultimately toward the Keys actually began close to his childhood home in Ocean Township, New Jersey, when he was 6 years old and his father took him to an airshow at Lakehurst Naval Air Station.

“You know, that’s where they have the huge blimp hangars, and where the Hindenburg zeppelin burned in the 1930s,” Pontecorvo said. “There was an act in the airshow with Snoopy and the Red Baron, and I watched as they brought a Sopwith Camel and a Fokker Triplane out of a hangar. I was hooked. What 6-year-old kid wouldn’t be?”

Despite the early obsession with aviation, Pontecorvo did not take the storied route of beginning flight training during high school and soloing at 16 because he “had to try the corporate route first.”

After years of work as a tax accountant he took a vacation in Key West and “never came back.”

Exploring Beyond Key West

Whether traveling by light aircraft or rental car, there is at least one stop all pilots should make.

In truth, “must” is a better word than “should.” The Florida Keys Marathon International Airport (KMTH) is the one other public field once you reach the Keys. About 40 nm short of Key West, Marathon airport alone is worth a visit, and the town is surprisingly packed with things to see and do.

During our trip in March, Alex and I drove the two hours from Islamorada to Key West. We also planned to drop in for a visit to the EAA Air Museum, which members of organization’s Chapter 1241 operate in a working hangar on the field at Marathon.

Museum staff, all volunteers, maintain the displays, which include a homebuilt replica of a World War I Fokker Eindecker fighter, a Piper Cub, and a Beechcraft C-45 Expeditor, which is a military version of the Model 18, widely known as the Twin Beech.

The museum is chock-full of aviation memorabilia, historical documents, books, magazines and manuals, scale models, and an impressive collection of desktop flight simulators, some dating back decades to a time before personal computers.

The chapter runs a Young Eagles program, hosting a range of youth events and providing free airplane rides and aviation education to young people from 8 to 17. The group also gives guided docent tours that include local aviation history.

When Alex and I stopped by, it was clear the museum was closed, but we could see someone inside. It was chapter member Mike Dann, who was kind enough to let us in, give us a tour, and share engaging conversation. I think the fact that I am a card-carrying member of the Experimental Aircraft Association helped our case.

Dann is a retired airline pilot who flew 727s, 757s, and 767s after an Air Force career at the controls of an E-3 Sentry, also known by its acronym, AWACS.

After a while, fellow member and museum volunteer Steven Walters arrived, wearing a flight suit and having just finished a mission with the local Civil Air Patrol. Walters, also an Air Force veteran, flew the B-1 Lancer—the “Bone”—before transitioning to flying cargo for FedEx as a civilian. The two men were generous with their time and hospitality, and by the time Alex and I continued on our way to Key West, two hours had passed. That’s what happens when you start chatting with airplane people.

Exiting the hangar, we heard the unmistakable sound of a radial engine overhead. We looked up and saw the culprit—a Vultee BT-13 Valiant, flown by Sol Bradman, owner of Island Warbirds. Bradman offers visitors more than just rides. He packages a detailed historical experience, right down to a World War II-era Jeep that takes guests to an authentically outfitted briefing room for preflight preparations.

We watched Bradman land, pick up the next passenger, and take off again. It was a busy day. I will have to make an appointment to return, though, as I have been interested in BT-13s since childhood and had never seen one flying.

What Bradman calls the “Warbird Experience” includes taking the controls and flying the vintage bird. The Valiant landed between two dominant aviation classics in the wartime flight-training continuum—the Boeing PT-17 Stearman primary trainer and the North American AT-6 advanced trainer. Those two models are renowned and sought-after while the BT-13 seems to have gotten lost.

Bradman holds commercial, ATP, and seaplane ratings, is a single engine, multiengine, and instrument instructor in airplanes and a helicopter instructor as well.

Beyond the airport, Marathon Key is a favorite among all types of visitors and is known for its marine life centers, beautiful beaches, and historical attractions. Some visitors prefer Marathon’s laid-back, family-friendly reputation to that of Key West, which can get a bit too festive for some visitors’ tastes.

Marathon’s most notable attractions include tours of the Turtle Hospital, a veterinary center specializing in sea turtle rehabilitation, the Dolphin Research Center, where visitors can learn about the ocean mammals, see how they are trained, and book appointments to swim with them, and Florida Keys Aquarium Encounters, where you can handle and feed nurse sharks, rays, and other sea creatures, and swim with them in large tanks.

Marathon’s Sombrero Beach is known for its fine white sand and is considered among the Keys’ most beautiful beaches. Pigeon Key is also worth a visit. The 5-acre island is accessible by walking along the old Seven Mile Bridge, which is no longer used by cars, or via ferry. The island features historic buildings and a museum that covers the history of the Overseas Railroad developed by Henry Flagler in the early 1900s. Flagler, who founded Standard Oil, is also known for building Florida’s East Coast Railway and turning the state into a popular destination.

Truthfully, the Keys are among few  places where the scenic drive can compete somewhat with a scenic flight. Flying still wins out, of course, and after landing at KEYW you will still want a car for getting around town. If you can, plan to spend at least two or three days exploring the area’s history, culture, food, and drink.

Whether or not you have affection toward Hemingway or his writing, you will have to admit that he knew how to pick a place. Key West has a lot of treasures to unpack, and if you try to do it on a day trip, you are sure to suffer some degree of disappointment. It really is the ultimate objective when traveling in the Keys. It is best to embrace that fact and enjoy it.

While we recommend the entire Key West experience, there are a few spots you should not miss: the Hemingway Home & Museum, where you can book a remarkably revealing tour, and Hemingway Social Club, for great decor and an authentic “Papá Doble” daiquiri, and Key West Cuban Coffee, a sweet, family-run lunch shop that flies under the radar.

As seaplane pilot Pontecorvo will tell you, flying as low as safely possible is especially rewarding in the Keys.

“I rarely take my passengers above 500 feet,” he said. “That way they can see the dolphins, the rays, the manatees—everything.”

This feature first appeared in the July/August 2026 Issue of Plane + Pilot magazine.