A Look Back… Bird’s Eye View of Fort Myers Beach



When I was a boy of seven, maybe eight, my father came across an ad in the newspaper for 20-minute flights from the Griswold Airport in Madison, Connecticut where we lived. This was nothing more than a small field with a landing strip, paved, for single engine planes. On a Saturday morning we headed to the privately owned airport, all of 15-minutes from our house and registered to take a flight.

First Flight

This was a first for me. Our family did not take family vacations that required flying. We drove to Cape Cod every year, and did some weekend get-a-ways in New York and Rhode Island.

Being a young boy, I was excited and somewhat nervous. I can’t recall who our pilot was, but he and my father struck up a conversation as we walked out to the plane.

“Great day for flying,” I remember my father saying.

“Every day is great for flying,” responded the pilot.

I climbed into the back of the plane and my father sat shotgun. As the pilot went through his preflight checklist, he asked my father, “Where do you live?”

“Up in North Madison,” he replied.

“We’ll head over that way once we’re clear.”

The pilot radioed into the tower, started the engine, and we taxied off the grass field to the runway strip. As he prepared the plane for takeoff, I remember how loud it got in the plane. Deafening, had I not been wearing earmuffs. While the pilot and my father had headsets and could communicate, I had only earmuffs and for the next 20-minutes was in my own world.

We gained enough speed and became airborne just before a clump of trees at the end of the runway. Immediately off to left, I could start to see Hammonasett Park and Long Island Sound. As we began to gain altitude, I could see the beach, and rows of houses that lined the shore.

The pilot circled toward the right and we followed Route 79 up to North Madison and made a pass over our house. I clearly remembered waving through the small porthole-like window, thinking my sister and mom could see me, if they were even outside looking for us.

Not sure if my father snapped any pictures during the flight, but I recalled the pilot letting him have control the plane for a bit. Gently my father eased the controls back and nose of the plane climbed up. He leveled it off and flew the craft for about five minutes.

Moments later came time to land. In my eight-year-old mind, this is when most planes crash. The plane flew, what seemed to be inches above the tree tops, bumped a few times as it connected with the pavement, and we rolled to what was a smooth landing.

“How did ya like it,” asked the pilot as he helped me climb out of the back.

“It was cool,” I replied.

It would be another ten years before I ever flew again. There was one time during our family summer vacations in Cape Cod, that we had a similar offer – to fly around the Cape for 20-minutes in a single engine plane. Although, the plane could only carry three passengers and the pilot. I opted to sit this flight out allowing my parents and sister to go on the flight.

My next flight was in 1987. It was my first time aboard a jet airliner, and as the song goes, I was head’n to California. That flight went well from what I remember. I’ve since flown, as far as jet airliners go, too many times to count. Back and forth to California, Florida, Europe, North Dakota, and other places.

Flying Small Again

My last time aboard a jet airliner was my visit to Connecticut in the summer of 2013. I realized then, I don’t like flying. At least commercial flying.

Recently at a networking event I had the pleasure of meeting Earl Leamer and Marsha Werbrouck Gregory, who belong to a volunteer group called Sundowners of Lee County. Every weekend at sunset, on a rotating schedule, volunteer pilots and observers patrol the waterways of Lee County as an auxiliary for the Coast Guard. During that meeting, Earl announced that the organization was looking for more observers. My friend, Peter Christiansen and I decided to inquire.

The first Wednesday of the month is their regular meeting and we both attended, signed up, and were eager to fly.

A few weeks later, I got an email with the flight schedule and I was assigned to Sunday, Feb. 4 for my first flight. This would be my first flight on a single engine plane in almost 40 years.

I arrived at the Page Field Airport, all of five minutes from my condo, and greeted the other observer and the pilot. After the pilot went through his pre-flight checklist, we put on our life vests, contacted the Coast Guard that we were taking off in ten minutes, and we began to taxi out to the runway.

I forgot how deafening it is in the cabin of a single engine plane. Luckily this time, unlike 40 years earlier I’m able to communicate with the pilot and the other observer riding shotgun.

During these patrols we monitor the vessels along the Caloosahatchee River, the canals in Cape Coral, the waters in Pine Island, Matlacha, to the Boca Grande Pass, then the beaches of North Captiva, Captiva Island, Sanibel Island and Fort Myers Beach. We count all the boats in the water and report any distressed vessels as well as any suspicious activity to the Coast Guard.

The Patrol Flight

As we took off and began to circle back to cross the Mid-Point Bridge, I could see the Fort Myers Country Club. Looks like an easy course from the air, but having played there quite a few times, I know differently. In my mind, I was thinking that somehow having this view could perhaps give me a slight advantage the next time I play there with my father, and David Staver (editor Santiva Chronicle), but my game needs more help than an aerial view can provide.

After crossing the river, we headed up to Pine Island and Matlacha. From the air I could easily spot Bert’s Bar where my father and I had lunch after a morning round of golf in Bokeelia. It’s amazing how everything is put into perspective having a view from the sky.

We flew a bit further north, then over the Boca Grande Pass and headed slightly out into the gulf. Then we passed over Cayo Costa, a very small island with a rich history, before rounding the tip of North Captiva Island.

Hard to imagine that at one time North Captiva Island and Captiva Island were one, and that two hurricanes (1921 and 1926) tore through the land and divided it.

The Landmarks

As we made a pass over the beach, I was reminded of all the history that created this small island. Having walked around Fort Myers Beach many times, seeing it from the air I was amazed.

To our left was Bowditch Point, where at one time was slated for a lighthouse that never happened. Bowditch Point Regional Park is a 17-acre part recreational park and part preserve area. The park features tables and grills, a concession area, restrooms and changing facilities. Visitors and locals enjoy bird watching and photographing the panoramic views of the gulf.

From the sky, the pier (officially known as the Fort Myers Beach Fishing Pier) juts out into the Gulf. It was crowded with people fishing and others staring out into the open water daydreaming, perhaps waiting for the sun to set. I tried to imagine other piers that at one time also jetted out into the Gulf and provided great fishing opportunities as well as a place to dock your boat.

The first one to come to mind was the Winkler Hotel (later the Beach Hotel) pier. Dr. William Winkler constructed a three-story hotel on the beach in 1912, along with a pier. Having seen a great historic aerial photo of the hotel and pier, I scanned the beach wondering exactly where his hotel had sat. The pier was destroyed in the 1926 hurricane and Winkler never rebuilt it. He sold the hotel business in 1930, and the building itself was tore down in the late 1970s.

I could also see Times Square which sits at the foot of the pier. Times Square is known as the heart of Fort Myers Beach offering everything from dining, gift shops, to street entertainers. It is unique and has its own charm; however, more recently a group of developers are proposing an entirely new layout for the adjacent area.

The last of the landmarks we flew over was the Matanzas Pass Bridge. Although the bridge was constructed 1978 and opened the following year, I pictured seeing the 1921 wooden drawbridge as well as the 1927 swing bridge. I imagined how for 50 years the bridge swung back and forth to allow for both vessel and automobile traffic. It survived boat crashes, three hurricanes, and a tremendous amount of wear and tear. A few years ago, I walked to high point of the arch of the Matanzas Pass Bridge, but it doesn’t compare to the view from the small airplane.


After making a pass over Fort Myers Beach, we contacted the Coast Guard to advise them that we were terminating our patrol flight. Minutes later, a smooth landing at Page Field Airport.

I’ve completed more than a dozen flights, but it never gets old viewing the islands and Fort Myers Beach from a birds view.

M. Jacobs

Southwest Florida historian T. M. Jacobs serves as an advisor to the Southwest Florida Historical Society and is a regular contributor of articles about early life on the beach.