Road trip: Mangoes, kayaking and Brad Pitt.
My love affair with Pine Island started right after Hurricane Charley swept through in 2004. Tampa Bay was supposed to get hit, but at the last minute Charley had other plans. For the five not-quite-towns on Pine Island — Matlacha (matt-luh-shay), Pineland, Bokeelia (rhymes withe Cecilia), St. James City and Pine Island Center — our good fortune was their tragedy.
But our tragedy is also their good fortune.
See, Pine Island is one of the only remaining barrier islands on Florida’s west coast that doesn’t have sandy beaches, which means it also doesn’t have a lot of appeal for developers. What it does have is fishing, kayaking and a sort of charm you don’t often find along coastal Florida — because there’s nary a sandy beach in sight.
What’s that, you say, no beach? On a barrier island? How on earth did that happen — and what’s the point of going there if there’s no beach?
Well, it happened in part because of the Great Depression. Sort of. As for reasons to go? Uh, sublime kayaking, a mango festival and it’s not your typical tourist town (or any type of tourist town).
Back to the island’s beginnings: Because of a land boom of the 1920s (moreso the inevitable bust that followed), the 1926 hurricane, and the 1929 medfly that decimated the citrus industry, Florida had a jump start on the Great Depression — to quote Alabama’s Song of the South: “… Well somebody told us Wall Street fell/But we were so poor that we couldn’t tell.”
So when this little island got connected to mainland Florida round about that time, priorities weren’t on development. When the economy rebounded, for whatever reason — perhaps because it lies between the mainland and Sanibel/Captiva — no one got around to razing the mangroves encircling the island.

Today, those mangroves protect the island in more than one way — not only from erosion, but, as a protected tree, from developers. With no sandy beaches (and really only one tiny bay beach), hoteliers have seen little reason to invest in the island.
That’s not to say you won’t find paradise there — those mangroves make for enthralling kayaking, and the Great Calusa Blueway — 190 miles of southwest Florida saltwater tempting you to try it — runs through here, and the island does have outfitters.

At least one of the few few motels that live here offers the use of kayaks — Knoll’s Court, with six rooms and conch-shell pink doors, epitomizes the type of lodging you’ll find. It fronts the water, with a sea wall mysteriously devoid of mangroves. Bokeelia, at the island’s northern tip, boasts some inns and B&Bs, but the main industries here rely on the land and sea: fishing, landscape plants and citrus. A “planned community” — Calusa Ridge — showed horrible promise before Florida’s most recent land bust, but today the bulk of the lots sit empty, with native vegetation slowly winning the battle where land was cleared for homes that never came to pass.

The locals celebrate their spectacular growing season with the annual MangoMania, a two-day festival celebrating not only mangoes but all the tropical fruits grown on the island. Should you decide you need something more substantial, one of my standby breakfast places, The Perfect Cup, makes an egg dish called Irish Eye you should try before you set off exploring.

As you explore, keep in mind this is the home of Florida mystery writer Randy Wayne White. You can easily find his home, an unassuming frame home perched atop an ancient mound. He wrote perhaps his most powerful work (from a Florida junkie’s perspective) — Dark Light — in his shed-turned-office in the days following Charley, as the island struggled to recover.

Next door, the Randell Research Center is the reason so many things here are named “Calusa whatever”: This archaeological site — it covers 67 acres of a 100-acre shell mound fronting the western edge of the island — is some of the last remaining evidence of the Calusa people. It also represents one of the northernmost places they lived; their population — which may have been as high as 50,000 at one point — stretched from here to the Everglades’ Ten Thousand Islands.
Of all Florida’s indigenous peoples, the Calusa have the fiercest reputation, and from what archaeologists have unearthed from the few remaining shell mounds, they were intensely attractive. Think about it: they lived on fish and fruits and vegetables (so they had some great muscles), they survived as fishermen so they spent a lot of time outside (they had a tan), and archaeologists know they were tall with long flowing hair. I essentially picture Calusa men looking like a tall, tan version of Brad Pitt (sans beard). The Calusa are long gone (thanks a lot, Conquistadors!), in part because — as the Florida Center for Instructional Technology gravely understates, “The first Spanish explorers found that these Indians were not very friendly.”