Old San Juan is a shopping mecca by day, but by night it is the center of Caribbean nightlife. The range of bars and nightclubs is incredible. From classical and cabaret to grunge rock and salsa, the offerings are world class.
Since the Old City is so small, it is easy to explore the entire area in one night. At the top of the hill along San Sebastian, smaller "grunge" bars and bars with local flavor are predominant. Along the bottom of the hill near the cruise ship terminals and Plaza Colon, there are well-known chain bars and restaurants. Calle Fortaleza and Calle San Francisco are lined by smaller venues with catering to specific genres.
Many festivals and block parties are held throughout the year. It is common to see San Sebastian blocked by partygoers. The plazas often host events (these can be found on La Bochinchosa's Event Page).
Paseo de La Princesa is a favorite for lovebirds and the romantically inclined. Caleta de San Juan which extends from the San Juan Gate to El Convento is a magical street encased by ancient trees and vines, ending in a breathtaking view of San Juan Bay.
The Old City has numerous performance venues that are listed on La Bochinchosa's entertainment page.