The last Friday night of every month is the best time to visit. Aim for the strip on 8th Street (Calle Ocho) around 11th - 14th Avenues. The art galleries all have open house, there are bands and dancing on the streets. The restaurants are overflowing. My favorite is El Pub: where else can you get great lamb shanks for under $10? Just don't expect anyone to speak English.
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