On a 10 day trip to Cuba, we spent 6 in Havana, staying in Old Havana, where we endlessly walked to all the squares, sometimes on a quest to discover the "best" mojito (Bar Bilbao's was our "winner", especially with their house band and sax player), other times merely picking random narrow streets to amble down, getting a feel for urban Cuban life, which turned out to be pretty hard scrabble. Walking the Malecon at dusk was adventurous, with folks hanging around in small groups, socializing, attractive women with suggestive advances and rudimentary fishing off the Malecon's wall which borders the Gulf of Mexico.
Musically speaking, we dined at Café Taberna to see the Buena Vista Social Club band, followed by the Tropicana, smoking cigars, drinking Havana Club rum and enjoying the Vegas-style show. At both, we got in the spirit, dancing on stage with others.
Other notable stops were several Hemingway bar hangouts (Floridita, Ambos Mundos) and his house in the hills. We took 50's American taxis to get to outlying upscale neighborhoods of Havana like Vedado and Miramar. We walked down 5th avenue amid all the foreign embassies and Raul Castro's residence, the Callejon of Hamel music venue in a small alley which we found with the help of a Santeria lady, dressed all in her distinctive white garb.
Our memories will always be of the friendly people, their music, their hardiness, entrepreneurship and ethnic heterogeneity, Havana being a crossroads for traders for centuries.