Naples is the end of the Tamiami Trail on the Gulf of Mexico, and after a long ride across the wet flat heart of southern Florida, it can feel almost unreal. The town is a polished, prosperous resort of about twenty-one thousand people with white sand beaches, a long wooden pier, palm-lined avenues, golf courses and some of the most expensive real estate in the state. Retirees, snowbirds and yachts are everywhere, and the air smells of salt and suntan lotion.
The Tamiami Trail, US 41, was built in the 1920s to connect Tampa to Miami, and the name is a contraction of the two cities. It was a monumental piece of engineering for the time, as the road was cut through the Everglades and the Big Cypress swamp, with dredges digging a canal beside it and using the spoil to build the roadbed. It opened in 1928, and the highway transformed southern Florida by connecting the Gulf and Atlantic coasts. It also altered the flow of water through the Everglades, an effect that is still debated and under restoration.
The ride across is long, flat and straight, with scenery that is wilder than most people expect. The road passes through sawgrass marshes and cypress forest, with canals running alongside, where alligators bask on the banks and herons and egrets stand in the shallows. Limited chances to overtake mean you will often follow slow traffic, and the heat is heavy, with high humidity from May to October, so early starts and plenty of water are a good idea. Thunderstorms burst in the afternoon, and mosquitoes are fierce in the wet season.
Naples itself has all the services you could ask for, with fuel, restaurants and lodgings at every price, though the prices are high. The pier has been battered by hurricanes and rebuilt more than once, and in the evenings people gather to watch the sun go down over the gulf. Fresh Gulf seafood is excellent, with stone crab claws in season from October to May, grouper sandwiches and shrimp. Winter, from December to April, is the best time, with mild days, dry weather and clear skies, but it is also the busiest and most crowded.