A 2-block stretch of 3rd Street South, at Broad Avenue, aspires to be the Rodeo Drive of Naples, but with the conspicuous absence of Gucci, Prada, and Tiffany, it remains an ordinary (albeit lovely), pricey place for browsing. The window-shopping here is unmatched. Pick up a free brochure from the chamber of commerce's visitor center; it lists the merchants and has a map of the area.
The 5th Avenue South shopping area, between 3rd and 9th streets south, is Naples's hottest wining-and-dining spot, complete with requisite Starbucks. The avenue is longer and a bit less chic than 3rd Street South, with its stock brokerages and real-estate offices along with boutiques and antiques dealers.
Also in Olde Naples, the rustic, tacky Old Marine Marketplace at Tin City, 1200 5th Ave. S., at the Gordon River (tel. 239/262-4200), has 50 boutiques selling everything from souvenirs to avant-garde resort wear and imported statuary. There are more boutiques in the Dockside Boardwalk, a half-block west on 6th Avenue South.