Fort Myers waterfront

Night falls on the Caloosahatchee River in Fort Myers. PHOTO BY DAVE POLLARD /Toronto Sun

Classic cars and snappy songs.

And, maybe, if you’re lucky, a cheeseburger in paradise.

Yes, Fort Myers and the surrounding area, including Captiva and Sanibel islands, has all that – it was the winter home of Henry Ford (and Thomas Edison, for that matter), hosts the annual Island Hopper Songwriters Fest, and nearby Cabbage Key was allegedly the inspiration for one of Jimmy Buffett’s more well-known songs – and more for Canadian snowbirds to discover … if your timing is right.

Fort Myers, roughly 200 km south of Tampa on Florida’s west coast, is a spectacular city of less than 100,000 souls – it jumps to nearly 800,0000 for the entire area, including Fort Myers Beach, Cape Coral, Captiva and Sanibel – that consistently bucks the typical Florida tourist trend.

Most of what Florida sun-seekers are after, the warm rays, sandy beach and salt water, are obviously plentifully available year ’round but – here’s where the timing issue comes in – but if you’re looking to see some of the best live music in intimate environments, you’ll need to wait until September, when the annual Island Hopper Songwriter Fest is held in the Fort Myers area. We’ll get more into that later.

Uncommon friends statue

The ‘Uncommon Friends’ sculpture of Henry Ford, Thomas Edison and Harvey Firestone on the city’s waterfront gives a glimpse of Fort Myers’ histoty. (DAVE POLLARD/Toronto Sun)

I started my three-day stay in the Fort Myers area with a boat trip to 112-acre Cabbage Key Island for lunch, ostensibly to tuck into a cheeseburger in the Cabbage Key Inn and Restaurant, the old-Florida style eatery that, according to a local legend, inspired Buffett to write the song “Cheeseburger in Paradise.” Proof Buffett actually visited the restaurant can be seen in the signed dollar bill – the place’s walls and ceiling are covered in the bank notes – over the bar but other places also lay claim to being inspiration for the tune.

The stop at Cabbage Key’s restaurant, which was built atop a Calusa Indian shell mound with the accompanying inn in 1938 by American playwright Mark Roberts Rinehart, was part of a five-hour tour courtesy of Captiva Cruises ($45 for adults). The boat, which leaves from McCarthy’s Marina on Captiva Island (give yourself an hour to drive from downtown Fort Myers), is a great way to visit Cabbage Key, where you can walk a nature trail or climb the historic water tower and check out the incredible panoramic view.

Heck, sitting on the patio outside the restaurant with a cold drink in hand might just be the best way to pass some time.

Cabbage Key Inn and Restaurant

Dollar bills adorn the walls and ceiling of the Cabbage Key Inn and Restaurant, purportedly the inspiration for Jimmy Buffett’s hit, Cheeseburger in Paradise. (DAVE POLLARD/Toronto Sun)

If you’re in the neighbourhood in September, it’s a must to stop in and check out live music at one of the many bars along Captiva’s Andy Rosse Lane and surrounding area during the Island Hoppers festival (this year it runs from Sept. 20-29). The names of the musicians who perform at the event, many of which are in intimate outdoor venues, might not be the most recognizable but they have written some popular songs performed by the biggest acts around.

Cabbage Key

The remote Cabbage Key Inn and Restaurant, as seen from the water. (DAVE POLLARD/Toronto Sun)

This is an excerpt from an article published by Dave Pollard on