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San Jose has a lot of great night spots, but more often than not they are hard to find. So here are a few great choices.
Jazz Cafe: Located in San Pedro, the Jazz Cafe doesn't always feature Jazz. The music changes on a nightly basis, from Jazz to blues to Reggae and drums, it's a very comfortable, nice laid back bar with great live music. Within walking distance to the Calle de la Amargura if you're looking for a little more crazyness.
Lubnan: You might not think of San Jose as being home to an amazing Lebanese restaurant, but it sure is. And on Wednesday nights, it's the busiest place in the city. There's a tiny little bar behind the restaurant that features local DJ's who are very competent on Wednesday nights. If you go, get there early if you're looking for a place to sit. If you eat, try the Shishkabobs, mmmm. Have a pull off a hookah for an after dinner delight. Lubnan is located right on Paseo Colon, directly across the street from Scotia Bank.
Los Perales: This is a local secret. You won't see any tourists in this place. The food is good and cheap, and it's almost always full but never overcrowded. Great place to have a bite and a beer. If you're on the east side of town, take a taxi to Curridabalt, then up the hill from the AMPM. Straight after the first stop sign, then left at the second. Go down about 200 meters and it's on the right hand side. You won't regret going out of the way to try this place out.
Retro: This bar is located near Mall San Pedro, in between the roundabout San Pedro and la Bandera, on the east side of the street. If you see a Taco Bell, just look to the other side of the street. It's on the second floor, and it has a cool, but not over the top 80's theme. Good music and good prices, gets packed on the weekends.
Olio: Looking for a great atmosphere with good service ad quality Italian cuisine? Head to Olio in Barrio Escalante. In a cab, just tell the driver Barrio California Bagelman's, 200 meters norte. This brick lined bistro is great for couples and wine lovers. When the train passes within 10 feet of the building it makes things interesting.
El Pueblo: If you're looing for absolute madness, El Pueblo is all you. There must be 30 bars in this mish mash of shops and restaurants all crammed together. This is where most of the late night action goes down n San Jose. Just tell any taxi El Pueblo and they'll know where you're going.
El Cuartel: This is the spot on Monday nights. there are 3 or so bars that are interconnected and on Mondays you can flow freely between all of them. Just tell a cabbie El Cuartel de la Boca del Monte. Across the street there's a heavy metal bar if that's more your style.