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

Neighborhood Spotlight: Pine Island

From Bokeelia at the northern tip to St. James City at the southern end, every area has a unique story.

Shaped by mangrove-lined shores and serene canals, Pine Island is the largest island on Florida’s Gulf Coast, and yet it preserves its Old Florida charm.  

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Pine Island Pine Island

Located at the Randell Research Center, the Calusa Heritage Trail celebrates this region’s original inhabitants, the Calusa people. Follow interpretive signs that share information about this indigenous tribe, how they lived on the land, and how Southwest Florida has changed over the centuries. Visit the observation tower, which sits atop the site’s tallest shell mound.

Just across the street from the trail is Tarpon Lodge & Restaurant, a historical 1926 lodge that has been transformed as a premier dining destination. Order the catch of the day and a classic cocktail just as the sun sets over Pine Island Sound.

A stone’s (or a seashell’s) throw from the lodge is Pineland Marina where Island Girl Charters can take you island hopping to more remote barrier islands like North Captiva Island and Cabbage Key.

Cabbage Key

Travel north to Bokeelia, a land of tropical fruit farms and local farm stands. The freshest, sweetest flavors await at MangoMania, an annual festival that celebrates all things mango and more. Taste tropical fruits and juices, browse among arts and craft stands and listen to live music in this one-day event in July.

The Bokeelia fishing pier draws locals and visitors alike. No fishing license is required to cast a line from the bridge into Charlotte Harbor, where fish like grouper, mackerel and snook swim in abundance. A live webcam shows off a clear view of the bridge and the sparkling water surrounding it.

In Bokeelia, dine on the waterfront at Capt'n Con's Fish House, sharing a platter of seafood and devouring bowls of hot chowder. Lazy Flamingo 3 is accessible by car, but a more fun way is to dock and dine on an order of fresh oysters and conch fritters.

Museum of the Islands Exterior

On your way south to St. James City, check out the Museum of the Islands to see artifacts and archaeological treasures from the time of the Calusa people and beyond.

Hiking trails wind through pine flatwoods at Galt Preserve, a diverse area that has a dozen different plant communities from mangrove swamps to mesic flatwoods.

St. James City is known for its waterfront restaurants, where you can simply pull up in a boat. Don't miss Phuzzy’s Boat Shack, a local favorite located in an actual boat shack overlooking a canal. Grab a cold beer and enjoy the hot crab and cheese dip, or order everything you desire from the raw bar.

From the northern end to the southern edge, let Pine Island’s Old Florida style surprise and delight you.