By Kris Hundley

At the southernmost tip of Pine Island off Florida’s west coast lies St. James City.

One road leads in.

Miles of canals lead out.

Coming in by dinghy from an anchorage south of town, we find a maze of unmarked canals. Finally we spot a battered sign in someone’s yard identifying one of the waterways as Monroe, St. James City’s watery Main Street. Pontoon boats, commercial fishing vessels, sailboats and runabouts line both sides of the canal, parked behind modest homes that seem like afterthoughts.
 

At the southernmost tip of Pine Island off Florida’s west coast lies St. James City.

At the southernmost tip of Pine Island off Florida’s west coast lies St. James City.

- Kris Hundley for VISIT FLORIDA

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Pontoon boats, commercial fishing vessels, sailboats and runabouts line both sides of the canal, parked behind modest homes that seem like afterthoughts.

- Kris Hundley for VISIT FLORIDA


Someone has painted a seascape on the back of a house. A neighbor has palm stumps carved into Tiki gods. Further down, life-size statues of boys fishing – one painted black, the other white – are perched on a sea wall.  “No Wake” signs bob on docks as motorboats zip by.

Beyond the homes is a row of restaurants with thatched roof bars. We tie up outside Woody’s, where a guy with a gray ponytail is playing Steve Earle songs. The Friday night crowd seems more interested in the fried fish platter. A 20-something guy at the bar says he’s a native Pine Islander who has watched the town go from redneck to retiree. He remembers when Pine Island was known for its asparagus. He hopes someday it will be known for pot. 
 

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For a short distance, the canal parallels the channel that leads into town.

- Kris Hundley for VISIT FLORIDA

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Beyond the homes is a row of restaurants with thatched roof bars.

- Kris Hundley for VISIT FLORIDA


In the center of town, commercial marinas specialize in catamarans, hulking multi-hull sailboats that skim the surface like water bugs. We follow the canal, assuming it parallels the channel that led into town. It does, for a short distance.

Then it makes a 90-degree turn and heads east. Our 5 horsepower Nissan pushes us past rows of homes and boatlifts as the sun sets and the sky turns gold, then pink, then gray. The canal opens onto the Intracoastal and we start rounding mangrove keys, searching for our anchorage. Just as the light fades, we see our sailboat, anchor light beaming atop the mast, off in the distance.

The sea is calm, the engine holds, we reach our home safely with an important lesson learned: In unfamiliar waters, always return the way you came.

Part Six
Sails Full of Florida: Passage to Key West

PLACES TO REMEMBER