Naples Shopping

The grande dame of this historic shopping area is Marissa Collections, a women's clothing store that stocks pieces straight from the New York runway shows and has an in-store Michael Kors boutique. Shops with handcrafted home furnishings, restaurants, and eight major art galleries also share this strip.

The only outlet mall in the county is on the smaller side, with about 40 stores catering to budget-minded shoppers. Mid-tier designer brands like Coach, Geoffrey Beene, Izod, and Jones New York are joined by swimwear, home furnishing, book, and luggage outlets.

Leave it to Naples to give its new flea market a spiffy design, without a hint of the ramshackle that usually accompanies thrifty gathering grounds. The ambitious 90,000-square-foot project contains an Everglades-themed food court, winery, outdoor Tiki Bar, produce market, and over 160 vendors. Open weekends, and yes, it has air conditioning.

Luxury brands, cool cafes, and an open-air tropical setting with royal palms and waterfalls make Waterside the ideal window-shopping destination. Feeling recession-proof? Louis Vuitton, Hermes, Cartier, and Gucci are at your disposal – along with more affordable options like Banana Republic and Anthropologie. Nordstrom opens in November 2008.

The heart of the downtown area, Fifth Avenue is as much about wining and dining as it is about shopping its unique boutiques. Still, much can be gleaned about local style here, with jewelry and women's apparel the top draws. Be sure to check out the windows at The Wind in the Willows, a boutique that goes all out with holiday displays.

Nearly 60 non-chain clothing and home furnishing shops, art galleries, and restaurants sprawl along Venetian Bay's waterfront at this open-air Florida take on a Euro-style village. Even with the fountains, tile roofs, and brick pathways, it's unlikely to be mistaken for Italy, but it beats the typical mall formula.