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Pine Island, FL Towns: Great Food, Fishing, Art & People

Rorie and I got on the road early yesterday morning to check out some small Gulf Coast towns about an hour and a half south of Sarasota. Our adventure took us to Punta Gorda, where we picked up a rural 2-lane byway called Burnt Store Road, the only way to get to Pine Island after leaving the Tamiami Trail. Legend has it the road was named to “honor” a native Calusa Indian who burned down the General Store in retaliation for the tribe being pushed off their land. There wasn’t much to see on this 17 mile route other than farmland and the occasional housing development. But the brief boredom we experienced on this leg of the trip was well worth it because it brought us to the funky, colorful, artsy town of Matlacha (pronounced Mat-la-shay (pop. 735) and we did get to rock out to some great old 60”s music. After crossing what the locals call the “fishingest bridge in the world”, we immediately found and nestled into outdoor seats at Bert’s Bar & Grill ( This popular restaurant is literally on the water and features excellent grouper sandwiches and shrimp tacos. Rorie’s meal came with a pile of incredible, thinly sliced, crispy homemade potato chips which she was kind enough to share. Even dedicated road warriors need sustenance.

Berts sign

After a refreshing lunch, we headed to Pine Island with St. James City (pop. 4,105) at the southern end and Bokeelia (pop. 1,997) on the northern tip. This area is known for its amazing subtropical fruit farms (featuring mango, pineapple and papaya) and as the place to catch a variety of fish including the granddaddy of them all – tarpon. The main route to and through St. James (Stringfellow Road) dead ends at the water, and the nearby original schoolhouse from 1887 is now home to a popular dining establishment called The Waterfront Eatery. Next we headed north on Stringfellow Road to the beautiful town of Bokeelia. The trip from St. James City took us past numerous large nurseries featuring palm and pine trees. The road dead-ended at a former boarding house now called Capt’n Con’s Fish House. What a beautiful restaurant location it was with its panoramic views of the piers and water. Here’s a windshield shot from our car…

Bokeelia bay

As we headed back to Sarasota, we stopped again in Matlacha to poke around in the Crayola colored cottages housing art galleries, craft stores and souvenir shops. We saw Paul McCartney (and John, George and Ringo) at the Sgt. Peppers Lonely Hearts Club Band performance behind Leoma Lovegrove’s art gallery and shop. Leoma is a Beatles fan and famous Florida artist and her creative, vivid paintings and hippy style are amazing. She even has a handpainted, psychedelic VW van parked in her driveway.

The Beatles

Leoma's bottle art


Since it had been about 2 hours since Rorie had last eaten she was naturally starving and drawn to a sweet treats shop (there’s a big surprise) called Great Licks which serves Luxury of Queenies’ locally made ice cream. Queenie creates her decadent temptations using all natural flavorings and locally grown fruit. Here’s GL’s owner BJ Hickey, who gave us the lowdown on Pine Island’s history and his shop (he told us he “retired” 7 years as a teacher in Illinois and now works 7 days a week. But, he smiles a lot so it seems to work well for him). Rorie was smiling too after she devoured her Black Raspberry Chocolate Chunk cone (no she didn’t share it with me).

Bj Hickey Great Licks

Our total round trip racked up a mere 212 miles on the odometer and our pedometers weren’t much higher. We didn’t even walk enough to work off the calories from the chips and ice cream but we didn’t care. We had a great time, found nooks and crannies filled with artistic gems, viewed gorgeous scenery, and as always, met the most interesting people doing amazing things in small towns.

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