Begin your nighttime crawl through Toledo with a stop at Bar Ludeña, Plaza de la Magdalena 13, Corral de Don Diego 10 (tel. 92-522-33-84), where a loyal clientele comes for glasses of wine and tapas of calamares, olives, or ham that are as generous as the bar is small. Drop in next to Trébol, Calle Santa Fe 1 (tel. 92-521-37-02), to sample their wine, their excellent tapas, and their bombas (stuffed potato bombs). Another wine bar hangout is Enebro, on the postage stamp-size Plaza Santiago Balleros, off Calle Cervantes (tel. 92-522-21-11).
Toledo is quiet at night, with fewer dance clubs than you'd expect from a town of its size. If you want to hear some recorded music, head for Bar La Abadía, Plaza San Nicolás 3 (tel. 92-525-11-40), where crowds of local residents, many of them involved in the tourism industry, crowd elbow to elbow for pints of beer, glasses of wine, and access to the music of New York, Los Angeles, or wherever. Other spots to hit include O'Brien's Irish Pub, Calle Armas 12 (tel. 92-521-26-65), which seems more appropriate for the streets of Dublin than old Toledo. A crowd in their 20s flocks here, and there's live music every Thursday at 10:30pm.