Fifth Avenue South vs Third Street South: Two Streets, Four Blocks Apart, Nothing Alike

Old Naples has two commercial spines and the town has spent about eighty years quietly deciding it prefers whichever one it grew up with. They are four blocks apart. They could not feel less alike.

Fifth Avenue South — the boulevard

Wide, palm-lined, and designed to be walked down the middle of. Fifth Avenue is the main street in the civic sense: the galleries, the sidewalk cafés, the bougainvillea, the street performers on a season weekend, the wine bars with tables spilling out onto brick. It runs from about 3rd Street west toward the Gulf, and it is where the town puts its best face on.

• Best for: a first evening, people watching, gallery browsing, choosing a restaurant by walking past twelve of them.
• Busiest: Thursday through Saturday, 6 to 9 p.m., January to March.
• Parking: a free public garage off 6th Street South that most visitors never find. Use it.

Third Street South — the courtyard

Older, smaller, greener, and organised around courtyards and alleys rather than a boulevard. Third Street was the original commercial district of Naples, and it kept the scale. The buildings are low, the planting is dense, and the whole thing hides behind itself — the best parts are down passages you would walk past.

• Best for: a slower afternoon, independent shops, the Saturday morning farmers market, sitting in a courtyard with coffee.
• The farmers market: Saturday mornings, year round, and one of the genuinely good ones. Get there before 9 a.m.
• Two blocks from the beach and the pier, which makes it the natural pre-sunset staging ground.

What is actually between them

Old Naples itself, which is the best part of the walk and the part nobody plans. Low white cottages, banyan trees with roots across the pavement, brick sidewalks, and a street grid laid out in the 1880s that still runs straight down to the water at every avenue. Cambier Park sits in the middle with a bandshell and free concerts in season.

Walk the numbered avenues west and every single one of them terminates at the beach. That is not an accident of planning, it is the plan — the original town was surveyed so that everyone had a route to the Gulf.

Beyond the two streets

Bayshore Arts District

East of downtown along Bayshore Drive, and the counterweight to all the polish. Breweries, a botanical garden, a Sunday market, murals, and the least manicured commercial strip in the city. This is where the under-forties are.

Tin City and the Bayfront basin

Ten minutes' walk east from Fifth Avenue and suddenly you are on the water among working boats. Covered in more detail in the waterfront dining guide, but worth the walk on its own for the shift in register.

Naples Botanical Garden and Baker Park

South and east respectively. The Botanical Garden is a legitimately world-class 170-acre collection; Baker Park is a newer green space along the Gordon River with a path system that connects into the Gordon River Greenway.

A walking evening that works

1. 014:00 p.m. — Park in the 6th Street garage. Coffee and shops on Third Street South.
2. 025:15 p.m. — Walk west on 12th Avenue South to the Pier.
3. 03Sunset — On the sand, just north of the pier where it is less crowded.
4. 04After — Walk back up 3rd Street to Fifth Avenue for dinner. The whole loop is under two miles.

Fifth Avenue is where Naples entertains. Third Street is where it eats breakfast.