Naples, Florida
Naples faces west into the Gulf, which gives it sunsets over water and a sea that stays flat for most of the year, and it has more golf holes per resident than anywhere in the United States. The pier dates from 1888 and the old town behind it is low, shaded and walkable; the Everglades begin forty minutes east, which is the contrast that makes the place interesting.
Why go
Sunsets over water on Florida's Gulf coast — the beach faces west, which the Atlantic side cannot offer. A pier from 1888 — the town's social centre, rebuilt after every hurricane. The Everglades at forty minutes — sawgrass, alligators and a landscape with no relation to the beach. Golf density unmatched in America — around ninety courses in the county.
The character
Naples was founded in the 1880s by developers who thought the bay resembled the Italian city and named it accordingly, and it grew slowly until air conditioning and the interstate arrived in the 1950s. What it became is the most orderly resort town in Florida: low-rise by ordinance, shaded by banyans and royal palms, with a grid of streets running down to a beach that faces the Gulf and therefore the sunset.
The other half of Naples is the Everglades. Forty minutes east, the built landscape stops entirely and the largest subtropical wilderness in the United States begins — sawgrass prairie, cypress domes, mangrove estuary and around two hundred Florida panthers, the entire remaining population. Corkscrew Swamp and Fakahatchee Strand are within an hour. A visitor who spends the whole time on Fifth Avenue South misses the reason the coast here is different from Miami: the wild edge is not distant scenery, it is the county next door.
Places of character
Naples Pier — 1888, wooden, free, and where the whole town watches the sun go down. Fifth Avenue South and Third Street South — the two shopping streets, both low, shaded and walkable. Naples Botanical Garden — 170 acres of tropical planting, one of the best in the country. Corkscrew Swamp Sanctuary — an Audubon boardwalk through old-growth bald cypress, with wood storks. Everglades City — the fishing village at the edge of the Ten Thousand Islands, and the airboat gateway. Marco Island and Tigertail — the barrier island south, with a lagoon beach and shelling at low tide.
The way to do it
Do the beach in the morning and the swamp in the afternoon, or the reverse — the point of Naples is the contrast. Take the boardwalk at Corkscrew rather than an airboat if you want birds. Eat stone crab in season, from October to May, which is the local delicacy and genuinely worth the price. And walk the pier at sunset with everyone else; it is the town's only communal ritual.
One perfect day
Beach at seven when the Gulf is flat and the shells are freshest on the tide line. Breakfast, then the botanical garden before the heat. Drive east to Corkscrew Swamp for two hours on the boardwalk under old cypress, with alligators below the rail. Late lunch in Everglades City — stone crab claws, cracked at the table. Back through the sawgrass in the afternoon light. Swim, then the pier for sunset with half the town. Dinner on Third Street South under the banyans.
Grand hotels
Naples Beach Club — on the sand since 1946, rebuilt but keeping the position that made it. LaPlaya Beach & Golf Resort — north of town on Vanderbilt Beach, the quieter contemporary option.
When to go
Best expression: February and March — dry, warm, stone crab in season and the Everglades at their best for birds. Consider: November, before the season, with the same weather and half the rates. Avoid if possible: August and September, humid, stormy and in the middle of hurricane season.
The frame
Ideal stay 3 nights · Minimum 2 nights · Best arrival fly to Fort Myers, forty minutes north · Airport RSW, 55 km · Walkability the old town yes; the Everglades need a car · Best without a car no