Chiado, Lisbon
1. Former Prada model Miguel Duarte shows off his eye for all things aesthetic at his Café Heróis, which has lime-green walls and mod white furniture. By day, there are toasted sandwiches and inventive salads such as the Brazilian, with pineapple, mango, cheese, ham, and yogurt dressing ($7.50). After 10 p.m., the café morphs into a mellow cocktail lounge. Calçada do Sacramento 14, 011-351/213-420-077
2. Every item in Alma Lusa ("Portuguese soul") is manufactured within the country. The house specialty is whimsical jewelry--necklaces fashioned from steel zippers ($60), pins in the shape of sushi rolls ($10). The boutique sells playful furniture, too, including beanbag chairs custom-made with brightly colored canvas in place of pleather ($263). Rua do Carmo 17, 011-351/213-432-039
3. Amo.te Chiado, one of the five Amo.te cafés throughout the country, publishes a monthly arts-and-entertainment magazine of the same name. In addition, the café hands out free guides to surrounding areas, with especially useful listings on the hottest nightclubs and bars in Bairro Alto, Chiado's hillier--and rowdier--next-door neighbor. Calçada Nova de São Francisco 2, 011-351/213-420-668, amote.clix.pt
4. Perhaps inspired by Lisbon's storied contemporary art museum Museu do Chiado, also in the neighborhood, Mousse blurs the line between gallery and shop, at least in the way items are displayed. But the objects--everything from an old-fashioned women's toiletries kit with 1920s packaging ($56) to hand-crocheted lampshades (from $204)--are all for sale. Rua das Flores 41-43, 011-351/213-420-781
5. With only two racks, José António Tenente has fewer pieces of clothing in his boutique than most people have in their closets. Leading up to Lisbon's biannual Fashion Week (in March and October), the designer slashes prices by as much as 80 percent to make way for his new sleek suit jackets and evening gowns. Travessa do Carmo 8, 011-351/213-422-560
6. At the rooftop terrace bar at the luxurious Bairro Alto Hotel, the views stretch across the Tagus River and take in the Ponte 25 de Abril (a dead ringer for San Francisco's Golden Gate Bridge) and another Lisbon landmark: an illuminated, 360-foot-tall statue of Christ. Sipping a caipirinha ($10), visitors might wonder if they aren't in another Portuguese-speaking place, Rio de Janeiro. Praça Luís de Camões 8, 011-351/213-408-288, bairroaltohotel.com
7. Sisters Teresa and Joana Figueredos stock original paintings and handmade jewelry at their Lua de Champagne. Teresa, a former architect, sells her own abstract paintings (from $178). Her little sibling Joana's original designs include red pom-pom earrings (from $12). Each purchase gets popped into a miniature plastic bag and then sprinkled with a handful of sequins. Rua do Ferragial 3, 011-351/213-431-684
8. Hotels in Lisbon don't come cheap (see #6, where rooms start at $330). Hotel Borges is the rare good deal. It isn't going to win any style points, but the hotel has a central location on the main drag. A breakfast of coffee and rolls with jam, served in a stately room lit by chandeliers, is included in the rate. Rua Garrett 108, 011-351/213-461-951, lisbonhotelborges.com, from $78