Naples thrives on people from around the world who often see it as their ideal Florida dream. The beaches are textbook perfect: a white halo of sand bisects warm Gulf waters and the undulating dunes look tropically proper with stands of arching palm trees with their fronds shaking in the breeze. The town is sophisticated, too—European influences and home-grown Florida architecture meld with the sensuous tropical climate.
The area spreads out significantly into newer subdivisions, malls and golf courses, but in downtown, everything is compact and lovely. The hub of activity can be found around Fifth Avenue and the area known as Old Naples, centered on Third Street South, which are both within walking distance to each other. Besides shopping, eating and people-watching along these corridors, the ultimate reward for traversing the avenues from east to west is the beach.
The sidewalk ends at a small parking lot where a short boardwalk leads to the sea, not quite visible from the street. Beachcombers are as likely to have their dress pants rolled to their knees or be holding onto a pair of high heels (maybe a shopping bag under an arm) as those wearing swimsuits.
Downtown Naples budded as a small commercial district in the 1920s and grew as it became a fashionable winter destination. The 90s brought a growth plan to the area, which was quickly surrounded by more dining, shopping and entertainment developments. The plan was made to save the area and turn it into the heart of Naples again.
Today, new developments such as the glitzy Fifth Avenue Inn and businesses that have been in the area for ages selling jewelry, home décor and clothing, create a casually posh-yet-friendly ambiance. "Fifth Avenue is a true Main Street," says Lise Sundra, executive director for Fifth Avenue South BID.
Though there is plenty of shopping, the main draw for visitors is the large clutch of restaurants and places to get a drink at night. Nearly every restaurant and pub has a cafe setting with tables spilling out onto the sidewalk, perfect for people-watching on warm nights. Live music and festivals energize Fifth Avenue throughout the year, including like The Grape Escape Wine & Food Festival in November and family activities such as the Spooktacular in October and a tree-lighting and Christmas Walk during the holiday season.
Old Naples–Third Street South
Just a few avenues from Fifth, along Third Street between 11th and 14th avenues South is where to find the juiciest boutique hunting. The neighborhood has maintained its original 1930s-era buildings, and the mature landscaping elegantly spilling from enormous urns along pedestrian sidewalks add a polished, tropical vibe. Here, the shopping swings from the incredibly high-end clothing emporiums such as Marissa Collections, where you can snag a pair of this season's must-chic looks to C. Orrico, a Lily Pulitzer signature store and Tommy Bahama.
Home décor dens specializing in luxury lines of furniture are doors away from others selling pottery and dining collections that would be lovely on the lanai. Specialty jewelry stores such as Four Winds Gallery have a cool collection of Native American pieces edited by Susan and Tim Brick who journey to the Southwest every market season, and Aragon Jewelers has a penchant for Spanish-made baubles.
Restaurants and cafes are also plentiful; depending on the mood, shoppers can stop for a scoop of gelato, a glass of wine or have dinner al-fresco. On Saturday mornings, Third Street South is roped off to traffic for weekly farmers market. Fresh-caught seafood, grass-fed beef and, of course, locally grown produce entice browsers to fill their bags for the evening's meal.
The pretty, well-maintained pier is a big draw after time spent town. Just like the beach access off of Fifth Avenue, access is easily accessed at the west end of 12th Avenue South. The long 1888-era pier draws fishermen and tourists looking to catch glimpses of dolphins leaping up to catch their prey. Near the beginning of the pier are stairs that go straight down to the beach. If you're caught without your beach stuff, you can buy them at the pier along with snacks and concessions.
A stand is available that offers life jackets for kids to borrow and the clean, white sand is perfect for plopping down a beach towel to catch a gorgeous and colorful sunset.