Discovering Old Florida: A Day on Pine Island

Silhouette of a lone kayaker returning to the shore at a vibrant sunset

Pine Island is one of Southwest Florida’s last authentic fishing villages – with an artistic twist. Making your way over the bridge toward the island feels a bit like taking a trek back in time. Once you reach the other side, you’ll discover a sleepy, rural community where the breeze is salty and the locals are as friendly as can be. So, set your watch to island time and strap in for Old Florida fun on a day trip to Pine Island.


Driving westward from Cape Coral, the only land-based access to Pine Island has been called “The Fishingest Bridge in the World.” Perhaps because you’re likely to see some of Florida’s famous snowbirds – with coolers and tackle boxes – casting their lines from the shoulders of the road. 


Large flock of white pelicans resting in the shallow water along the beach

Before reaching the shores of Pine Island, our first stop is in the offbeat, fun-loving community of Matlacha. Barely bigger than your average subdivision, this tiny island is freckled with shops, galleries and funky waterside restaurants – most of which are swathed in polychromatic coats of paint. On Matlacha, swing by the Perfect Cup to fuel up for the day ahead. As the name suggests, they serve a pretty fantastic cup of joe. And, with breakfast dishes like their jumbo blueberry muffins and Crabby Big Daddy omelets – there simply isn’t a better way to start the day. Also, visit the brightly-colored bungalow that is Leoma Lovegrove Gallery & Gardens – and pick up original island art.

Early Afternoon

Once breakfast is squared away, it’s time to take to the water to explore the natural beauty of the preserved Florida coastline. The Pine Island Sound Aquatic Preserve spans the western coast of this 17-mile island and remains nearly the same as it was when the Calusa Indians first inhabited the area. Rent a kayak from one of the area’s many shops to explore mangrove tunnels and salt-water lagoons populated by majestic birds, scuttling crabs and an array of indigenous sea life.


After you’ve worked up an appetite on the water, make your way back to Matlacha for a scrumptious lunch – and if you’re lucky, maybe a story or two from the seafaring locals. Bert’s Bar & Grill boasts a colorful 70-year history, daily live music and some of the best burgers and wings this side of the Caloosahatchee. Before you go, check out their website to read about their interesting past and hear their custom (amazing) Jimmy Buffet-esque jingle. 



Group of three visitors enjoying a cold beer on the deck of Berts in Fort Myers

Now that you’ve gotten to know the locals, dig up a little history on the island’s past at the Randell Research Center on the northwest side of Pine Island. Here you can tour the Calusa Heritage Trail, a 3,700-foot interpretive walkway that leads you through the mounds and canals of the Pineland archaeological site. Situated on the one-time location of a Calusa Indian village, the center offers a unique and in-depth look at Pine Island’s earliest residents.


As the day winds down, it’s important to pick the perfect place to watch the famous Southwest Florida sunset. We recommend grabbing a fishing pole and setting course for Bokeelia, a cottage-strewn neighborhood on the island’s northern tip. The fishing pier there is known for its unbeatable sunsets and tarpon-rich waters. Undoubtedly, it’s the most picturesque locale to end your day on Pine Island. 

Dream up your own Pine Island itinerary by visiting our Pine Island community page.

Sunset Canoe

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