A Perfect Three Days in Naples

The first rule of a Naples itinerary is that it should be provisional. Look at the wind forecast the night before and put the water day on the calmest morning available. Everything else here is weather-proof; the boat day is not, and it is the day worth protecting.

Day One — Get your bearings, end at the pier

Morning

Start at Delnor-Wiggins Pass State Park at the north end of town. Get there by 9 a.m. before the lot fills. Walk north along the sand toward the pass, look for shells at the tide line, swim. Two or three hours here is not too long.

Afternoon

Lunch in North Naples, then Naples Botanical Garden for the cooler part of the afternoon. It is 170 acres and you will want two hours minimum.

Evening

Drive into Old Naples, park in the free 6th Street South garage, and walk down 12th Avenue South to the Pier by 45 minutes before sunset. After the light goes, walk back up 3rd Street to Fifth Avenue South for dinner. Do not drive between the pier and dinner; the whole point of Old Naples is that you do not have to.

Day Two — The water

Morning

This is the day. A four-hour charter out of the city dock is the format that works: Naples Bay and the canal neighbourhoods at idle speed, out through Gordon Pass, dolphins in the near-shore Gulf, then south to Keewaydin Island to beach the boat and walk the empty side.

Bring: polarised sunglasses, a hat, reef-safe sunscreen, a mesh bag for shells, water, and a cooler if the boat allows one. Small-group charters out of Naples Bay handle this route as standard.

Afternoon

Back in around 1 p.m., which is exactly when you want to be off the water anyway. Late lunch at Tin City or the Bayfront basin — you will already be tied up nearby. Then do nothing for two hours, which is a legitimate and underused Naples activity.

Evening

Bayshore Arts District for a change of register: a brewery, the Sunday market if the timing works, and dinner somewhere with no view and better fish.

Day Three — Inland and the edge of the Everglades

Morning

Corkscrew Swamp Sanctuary, 45 minutes east, and go early — the boardwalk is best before 10 a.m. for both wildlife and heat. Allow three hours for the full 2.25-mile loop with stops.

Afternoon

Either the Rookery Bay visitor centre on the way back, or push south to Marco Island for Tigertail Beach and the lagoon, which is the best shorebird spot in the county at low tide.

Evening

Saturday morning farmers market on Third Street South if your third day lands right; otherwise a final sunset at Lowdermilk or Vanderbilt, both of which have parking that will not test your patience on your last evening.

If you have five days

• Add a day in Everglades City and the Ten Thousand Islands — the working, unglamorous end of the national park.
• Add a full lazy beach day with no plan at all. Naples rewards this more than most destinations.
• Add a second water day. Almost everyone who does one wishes they had done two.