Head to the historical center of Plaza de Bolivar and near the Iglesia de Santo Domingo for shopping options of upscale resort wear, jewelry (emeralds are a Colombiana's best friend), and luxury handmade crafts. Café del Mar, a bar/restaurant in the northwest, has romantic, sunset views with a lively crowd, and outside the walls in the neighboring Getsemaní in the south (which used to be dangerous, but in the past five years has been bringing in both locals and tourists). Here you'll find Latin jazz heaven in Café Havana (which Hillary Clinton visited last year), and cumbia and reggae in the Bazurto Social Club.
The growing Bocagrande neighborhood has a bulk of tourist options that include more hotels (chains such as the Hilton), nightclubs and art galleries, and in short, feels like a casual South Beach. Venture out to the Rosario Islands from here for picturesque beach time.