Start in Five Points, where you'll find Edge City, a bold, quirky shop that carried Betsey Johnson's clothing before she had her own label. For dinner, trace the gypsy culinary trail from India to Spain with 13 Gypsies' menu featuring house-made chorizo-and-dates tapas paired with bottles of Spanish wine. The tiny, seven-table treasure box fills up quickly, so call ahead for reservations.
Saturday brunches are best at the über-chic 'town restaurant in Avondale. In the same building, the Emly Benham boutique serves as the city's Prada and Jimmy Choo purveyor. After browsing through the high-end handbags and shoes, relive your childhood with a chocolate malt and jawbreaker at the retro Florida Creamery and then walk it all off while enjoying views of the St. Johns River. For dinner try Orsay, a French-inspired dining room and lounge, where you can find house-made charcuterie plates of duck rillettes, pâtés, and foie gras mousse expertly matched with Pommery mustards and red onion marmalades.
Nightlife bustles in the King Street District. End your Riverside excursion with vintages from around the world at Walkers Wine Bar (904/894-7465), or one of the 84 beers on tap at Kickbacks Gastropub (904/388-9551).