The Best Things to Do in Naples, Florida — Written by Someone Who Lives Here

Naples has a reputation problem, in that its reputation is golf, shopping and retirement. All three are accurate and none of them are the reason to come. The reason to come is that this is the last stretch of the Florida Gulf coast where the water, the estuary and a genuinely walkable old town all sit within about four miles of each other, and the whole thing faces west into the sunset.

Here is what to actually do with that, in the order of how much you would regret skipping it.

1. Get on the water at least once

This is first for a reason. Everything distinctive about Naples is a function of the water — the town exists because of the fishing, the barrier islands, the pass, the estuary. From land you are looking at the edge of it.

The minimum viable version is two hours: out through Naples Bay, past the canal neighbourhoods, through Gordon Pass, dolphins in the near-shore Gulf, back at dusk. The better version is four hours and includes a barrier island. Small boats beat big ones for this — a six-person charter goes places a sixty-person catamaran cannot, and you can actually hear the captain. Local operators like Naples Luxury Boat Tours run the small-group version out of the city dock.

2. Watch a sunset properly

Not glance at one. Arrive forty-five minutes early, stay fifteen minutes after. Naples faces due west with open water to the horizon and the last twenty minutes of light here is the single best free thing in the city. The pier is the classic; Delnor-Wiggins is the beautiful one. Full breakdown in the sunset guide.

3. Pick the right beach for what you want

There are twelve miles of it and the beaches are not interchangeable. Delnor-Wiggins Pass State Park for natural beauty and shelling, Vanderbilt for convenience and a parking garage, Lowdermilk for families, Clam Pass for the mangrove boardwalk, Barefoot Beach Preserve for emptiness. The beaches guide breaks all of them down.

4. Walk Third Street South and Fifth Avenue South

Four blocks apart and entirely different in character. Third Street is courtyards, independent shops and a very good Saturday farmers market; Fifth Avenue is the palm boulevard with galleries and sidewalk dining. Do both in one evening with the beach in the middle.

5. Eat stone crab, in season

October 15 to May 1. It is the local fishery, it is genuinely sustainable, and it is the one food in southwest Florida you cannot get a proper version of anywhere else. Mediums are the value play. Buy them by the pound at a fish market if you want twice as many.

6. Corkscrew Swamp Sanctuary

Forty-five minutes east, and the best half-day inland in the region. A 2.25-mile boardwalk through the largest remaining old-growth bald cypress forest in North America, with wood storks, alligators, barred owls and, in the right winter, painted buntings. Go early, go on a weekday, allow three hours.

7. Naples Botanical Garden

170 acres organised by region — Brazilian, Caribbean, Asian, Florida — and considerably better than the phrase 'botanical garden' prepares you for. Morning is best both for temperature and for birds.

8. Rookery Bay

The estuary reserve south of town, protecting around 110,000 acres of mangrove. The visitor centre is the easy version; the boardwalks and the kayak launches are the real one. Details and hours at rookerybay.org.

9. Keewaydin Island

The undeveloped barrier island south of Gordon Pass, with no bridge, no facilities and considerably better shelling than anywhere you can drive to. Boat access only. Worth arranging an entire day around, particularly on a spring low tide.

10. The Everglades, from the western edge

Everglades City is fifty minutes southeast and is the working end of the park — stone crab boats, the Ten Thousand Islands, and the entrance to the Wilderness Waterway. It is a much less packaged experience than the Miami-side airboat operations and much more interesting for it.

The honest 'maybe' list

• Naples Zoo — good for a rainy morning with children, unnecessary otherwise.
• Waterside Shops and Mercato — very nice shopping centres that could be in any wealthy American city.
• Golf — Collier County has one of the highest concentrations of courses per capita in the United States, and if you came for that you already know where you are going.
• Marco Island — twenty-five minutes south, worth a day, particularly Tigertail Beach for birds.

What to skip

The large-boat 'sightseeing cruises' that carry a hundred people around the bay with a PA system; you see the same water with none of the quiet. And any tour advertising the Everglades that runs an airboat on a freshwater canal off the Tamiami Trail while calling it the Ten Thousand Islands — those are two different ecosystems and only one of them is what you were promised.

If you only do one thing here, do the one that involves leaving the shoreline. Everything else in Naples is visible from the road.