Source: Terry, aka cheersterry
1.) Start in the rooftop bar at the Inglaterra Hotel – great view of Parque Central, the theatre, etc. Quiet, no one to bug you. Great mojitos. Have one and move on.
2.) Go down to street level and have another cocktail at their sidewalk patio bar, the Galeria La Acera del Louvre. Watch the street action. Lots to take in, but again, you're slightly removed from it.
Head directly across the street, through Parque Central, past the large groups of shouting men who are just about ready (it appears) to kill each other. Don't worry, they're simply discussing baseball. If you really want to see some drama, put a video camera on them - their decibel level (and hand gestures) will double.
3.) Continue straight ahead past the Art Museum until you get to the famous landmark (and tourist trap) the El Floridita where Hemingway spent a lot of time slurping back daiquiris. Wander in, have a look, have an overpriced daiquiri if you must.
4.) Exit, turn left, and at the end of the block (corner of Monseratte and Obrapia) there's two good bars, the open air Castillo de Farnes, and the Bar Monseratte where you enter through an old fashioned saloon style swinging door.
5.) The Castillo de Farnes is a great people watching bar, the Bar Monseratte will be less hassle, and it has decent pub food and usually a pretty good band.
6.) Now, head back a couple of blocks to Obispo and take a right turn. There's several bars along this lovely stretch. Go into any of them that are rockin'. One of my favourites is the La Lluvia de Oro. Lots of tourists and well connected hustlers, and many times a good band.
7.) Continue down Obispo to the Café Paris. It's similar to the La Lluvia de Oro with good music and decent pizzas.
8.) Exit and make a right turn, south from Obispo, and enjoy a leisurely stroll down San Ignacio for 4 blocks until you reach Plaza Vieja. It has a lovely fountain (quite rare in Havana) in the centre. In the southwest corner is a trendy European style place that has its own micro-brewery. I forget its name. They have beer drinking contraptions that are about a metre high – you have to still be in a real beer drinking mood. Check it out as an example how Cuba can really screw-up a good idea.
9.) Go the northeast corner of the Plaza and you'll find one of my favourite classy places, the Taberna Beny More. Wonderful place.
10.) Exit and turn right, following one of my favourite restored streets, Mercaderes, back 3 blocks to Obispo, then another block further to O'Reilly. Turn left, and one block later slip into the O'Reilly Pub, and carefully negotiate the antique winding wrought iron staircase up to the second floor. Enjoy a moment of peace in the noise of Havana.
11.) After the 10 cocktail warm-up you've enjoyed to this point, you should be ready for some serious drinking by now, so turn left on O'Reilly and continue west for a couple of blocks until you reach the Bar Bilbao, one of the few truly Cuban bars left in the tourist section of Old Havana.
It's a dump. They don’t particularly encourage tourists, but once you’re there, its great. Have some real Cuban Pesos on you (not Convertible Pesos) and enjoy a double rum for 8 pesos, and a cigar for 1 peso. (1 Convertible Peso = about 25 Cuban Pesos. Do the math. We're talking cheap.) The decor - if you can call it that - is sort of interesting. The bar has been discovered by the professional soccer club from Bilbao Spain, and they have left all kinds of stuff all over the walls. Check out the poster of the Canadian Women's Soccer Team over the bar - in the bottom corner it says "We Love Terry and Wild Bill."
Go one block south, back to Obispo, and walk back to Parque Central.
At this point you've had a decent tour from Parque Central, down Obispo, through a few sections of Old Havana and back to your hotel. It's only a thumbnail tour though - there's a ton of great places I haven't mentioned.
The night is still young, and you have loads of time to start some serious drinking and dancing.
Have fun.
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