Three Days in Naples: A Plan That Works

The mistake visitors make in Naples is over-scheduling. This is a town with a rhythm — early mornings, slow middles, spectacular evenings — and fighting it makes for a worse trip. Here is three days that follows it.

Day one: downtown and the pier

• 8:00am — coffee in the Third Street South courtyards before anything opens
• 9:00am — walk the Old Naples grid: 3rd Street to Gordon Drive, banyans, cottages, no traffic
• 10:00am — Lowdermilk Park for the beach. Restrooms, shade, easy parking.
• 1:00pm — lunch downtown, then the shops on Fifth Avenue South while the sun is worst
• 5:00pm — Naples Pier, 45 minutes before sunset
• 7:30pm — dinner on Third Street South

Day two: on the water

Give the whole day to it. Morning water in Naples is glass-flat and the interesting places — Keewaydin, Gordon Pass, the Rookery Bay backwater — are only reachable by boat. A half or full day with a captain out of Naples covers all three, and it is the day people actually remember.

• 8:30am — depart; run south while the Gulf is calm
• 9:30am — swim and shell on Keewaydin Island
• 11:30am — mangrove backwater, dolphins, spoonbills, ospreys
• 1:00pm — lunch on board anchored in three feet of water, or dock and dine
• 4:00pm — idle back up Naples Bay past Port Royal
• 7:00pm — casual dinner at Bayfront or Tin City; you will be sun-tired and that is correct

Day three: north end and gardens

• 8:30am — Naples Botanical Garden, before the heat
• 11:30am — Clam Pass boardwalk, or Delnor-Wiggins Pass State Park if you want the better beach
• 1:30pm — lunch at Mercato or a beachfront bar at Vanderbilt
• 3:00pm — Vanderbilt Beach for the afternoon; the garage guarantees you a space
• 6:30pm — sunset from the north end, then dinner at Mercato

With four or five days

Add a day trip: Marco Island and Tigertail Beach, Everglades City and the Ten Thousand Islands, or Corkscrew Swamp Sanctuary inland for the boardwalk through old-growth cypress. All are under an hour from downtown.