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What's in a name? Back when the town of Naples was founded during Florida's 1880s land boom, promoters flooded northern newspapers with ads touting this area's natural beauty, mild climate, abundant fishing potential, and stunning bay-front views by comparing it to something a little more familiar.
While readers up north might have had no idea what the undeveloped wilds of the Gulf Coast looked like, they certainly knew of Italy's grand and luxurious reputation. The name stuck, and the city became something of a self-fulfilling prophecy. Once a small fishing center known for its decidedly unsexy industries like clam shelling and oyster processing, Naples quickly developed into a famous beachfront resort town — worthy of the Italian Riviera — that attracted Hollywood stars like Gary Cooper and Greta Garbo.
Nowadays, Naples is a city where luxury abounds. But despite its Waldorf Astoria and two Ritz-Carltons, upscale is not necessarily synonymous with exclusivity here. Travelers have access to many public golf courses and beaches, symbols of privilege which are often cordoned-off in other resort communities. And high-end shopping districts like Third Street South and Fifth Avenue South in historic downtown, or the Tin City Waterfront Shops, include a charming mix of chic boutiques, quaint art galleries, and accessible purveyors of funky local wares. Head to these shores if you're looking to indulge in finery without being overwhelmed by fuss.
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The 1920s tin-roofed buildings along Naples' waterfront are a reminder of the city's origins as a fishing industry hub, once housing businesses dedicated to clam shelling, oyster processing, and boatbuilding. Nowadays, they're home to the Tin City Waterfront Shops, a collection of over 30 boutiques, galleries, and restaurants, many owned by local artisans. Visit in the spring to take advantage of discounts offered during Naples' weeklong Spring CityFest.
Snowbirds aren't the only ones who make Naples a temporary home when it's time to take it easy. During summer nesting season, which usually lasts from early May through August, you may see sea turtles — especially the up-to-350-pound loggerhead species — laying their eggs in the moonlight on area beaches. If you don't want to leave your sea turtle encounter up to chance, visit the resident juvenile loggerhead at the Dalton Discovery Center at the Conservancy of Southwest Florida.
Revisit Naples' roots as the historic heart of Southwest Florida's fishing industry by trying your hand at saltwater or fly-fishing in the Gulf waters. Fall often ranks as a favorite season for local fishermen, as September through November is peak time for game fish like redfish, snook, bonito, tarpon, sharks, and Spanish mackerel. If you need a little guidance out there on the water, book a guided fishing tour with Captain Kyle Giampaoli at Tarpon Daze Fishing Charters.
During high season, from November through April, a walking tour comes free with admission at the 20-year-old Naples Botanical Garden, which features over 600 species of plants and flowers. In November, be sure to attend Hats in the Garden, a fashionable fundraiser luncheon and runway show that frequently includes in-person appearances by top designers like Michael Kors.