Naples, FloridaThings To Do
Palm-lined avenue in Naples at dusk with lit outdoor dining tables
Orientation

The parts of Naples

Six areas, each with a different day in it. Where you sleep here matters more than in most places, because the distances are small but the character shifts fast.

Old Naples, Naples FloridaLow, green, walkable and expensive

Old Naples

The original grid, laid out in the 1880s between Gulf Shore Boulevard and the bay. Streets are numbered avenues running to the water, shaded by banyans and royal poincianas, lined with cottages that survived and mansions that replaced the ones that didn't.

This is the only part of Naples where you can leave the car for a whole day. Beach in the morning, lunch on Third Street South, gallery browsing, then the pier for sunset — all inside a mile.

  • First visits
  • Walking
  • Sunset
  • Staying without a car
Fifth Avenue South, Naples FloridaThe dinner-and-evening street

Fifth Avenue South

Eight blocks of restaurants, courtyards and shopfronts under royal palms, kept deliberately low-rise. In season it hums from five o'clock; in August you'll have a sidewalk table to yourself.

Come for the evening rather than the middle of the day. Park once in a garage off the avenue, eat outside, walk the six blocks to the beach afterwards.

  • Dinner
  • Live music
  • People-watching
  • Rainy evenings
Third Street South, Naples FloridaQuieter, older, courtyard-shaped

Third Street South

Naples' oldest shopping district, tucked into the residential streets a few blocks from the pier. Bougainvillea over stucco, hidden garden courtyards, a Saturday farmers market that locals actually use.

If Fifth Avenue is the evening, Third Street is the morning: coffee, pastry, the market, then the short walk to the beach at 3rd Avenue South.

  • Breakfast
  • Farmers market
  • Slow mornings
  • Galleries
Naples Bay & Tin City, Naples FloridaWorking waterfront, and the way out to the Gulf

Naples Bay & Tin City

Everything that floats in Naples starts here. The bay runs from Gordon Pass north through Tin City's old clapboard warehouses, past marinas, charter docks and the mouths of the canals.

It's the least polished part of central Naples and the most useful: this is where you board anything with an engine, buy fish off the dock, and watch the tide turn.

  • Boat departures
  • Fishing
  • Casual seafood
  • Sunset cruises
North Naples & Vanderbilt, Naples FloridaResorts, garages, wide beaches

North Naples & Vanderbilt

From Pelican Bay up to Wiggins Pass, the coast turns into a run of resorts, condos and — crucially — structured parking. The beaches are broader here and the sunsets just as good.

Base yourself here if you want a pool, a garage and easy access to Delnor-Wiggins and Barefoot Beach, and accept a 15-minute drive to downtown dinner.

  • Resorts
  • Easy parking
  • Wide beaches
  • Families
Goodland, Isles of Capri & Marco, Naples FloridaWhere the Ten Thousand Islands begin

Goodland, Isles of Capri & Marco

Drive 30 minutes south and the coast frays into islands. Goodland is a fishing village of stilt houses and Sunday afternoon bands; Isles of Capri is three quiet keys with waterfront crab shacks; Marco is the big beach island with the high-rises.

This is the launching edge for the Ten Thousand Islands and Everglades backcountry — smaller, wilder water than Naples Bay.

  • Backcountry boating
  • Crab shacks
  • Shelling
  • Day trips