If you're thirsting for some live music and adult beverages, and you've left all pretenses of experiencing anything even remotely resembling the life of an actual Cuban back at the hotel, Calle Obsibo will be your tourist-laden oasis. This is the foreigner's lifeline in La Habana Vieja: a narrow, pedestrian thoroughfare connecting Parque Cetral with the Plaza de Armas, jam packed with all the bars, cafes, shops, restaurants and street vendors you could ask for. The avenue itself, which can get fairly dirty at times between the near-continuous construction work and the occasional downpour, is an almost literal melting pot of flavors and Latin/African/Caribbean rhythms, flanked on either side by some of the capital's more interesting colonial architecture like the Hotel Florida and the Taquechel Pharmacy.
Since the options are as numerous as the sensory stimuli here, recommending places to eat and drink would be somewhat futile. Follow the music, follow the wafting aromas, and when you're feeling parched, stop for a drink. This is a great place for an early-night pub crawl, but since bars close down at midnight you'll have to look elsewhere for some truly late night entertainment.
Location:La Habana Vieja, Havana, Cuba
Note:For you Hemingway buffs, it should go without saying that Obispo also houses two of the author's favorite haunts: the Ambos Mundos Hotel and El Floridita. That should be worth a couple rounds at least.