One of the things I enjoyed the most about staying in the Condado area was the number of places we could go to in the evening just to grab a drink. Perhaps the two places we enjoyed the most were the Barlovento and Hacienda Don José, both located within easy walking distance from the Condado Plaza. The Barlovento (http://www.barloventopr.com) is located at 1043 Ashford Avenue and it's open from 5:00 pm to 2:00 am (closed on Mondays). It is a really nice outdoor cafe with a good wine selection, which can be a nice change from rum after a few days in Puerto Rico (!). As for the Hacienda Don José (1025 Ashford Avenue; 787-722-5880), what we enjoyed the most about it was to be able to sit at a table at the back of the restaurant with the window open to look at the sea (though we had to laugh when the waitress warned us we might get cold!). I ordered what seemed like a Caribbean version of Long Island Ice Tea and it was very tasty! And of course, in between drinks, nothing beats going for a nice walk on the beach and watching the sunset :o)
Dress Code: Most places seemed pretty casual, even the lobby bars of some of the big resorts.
Only reason we made it here was because the helpful guy at the airport who was giving us our vouchers for the night said that it was a good bar to go to. We were stranded over night in San Juan with no luggage. He told me to go to the DragonFly and ask for a friend of his. I did exactly as instructed and his friend, who worked behind the bar, took care of us immediately.
Seeing as we had already been drinking for a while, the rest of the night was a blur, but we did get introduced to a load of people who took us around to other places.
All in all a great night with great people and again a great adventure for the memory books.
Dress Code: For some reason they don't like men to be wearing shorts and so they will insist that you wear a skirt (sarong) instead that they will provide for you to wrap around your waist. That way you can look even more ridiculous.
Lupi's has the best of everything. Great food, beer, entertainment and a good place to meet people. The food is a mixture of Mexican and Puerto Rican food. There is always something going on at night. It ranges from a local band, karaoke, DJ's or fashion shows. The atmosphere is very laid back. There is a good mixture of locals and tourists. I highly recommend Lupi's! I go there almost every night when Im in town!
Dress Code: Puerto Rico tends to be a little more dressed up than in the U.S. - Lupi's is casual. For women, if you show up in jeans/jean skirt and a nice shirt you are fine. I wouldn't recommend shorts and t shirts though. For men, jeans and a nice shirt will do just fine.
There are bars/pubs etc that are fun for those with their liver on their mind.. quite often though you find that the popular hotels ie Mariott (I think if my memory serves me correct) offers a lot of entertainment and contains a casino in it...
For those like me, if you just walk around you can find bars etc. I am pretty bad, I cant remember what the decent ones are called...I shall look back in my journal when I have time and check!! Drinks are reasonably priced as well! It's more the pub scene.
Dress Code: Well look at what Diana (my fellow companion) and Willie (local we met) are wearing :)
We shot a lot of pool and drank a lot of El Presidente while in San Juan, so, we naturally ended up at the Upstairs Bar & Grill a few times. Although the name is not too creative, there was no shortage of beers and pool tables at this sports bar. Good local crowd as well...
Dunbars is great place for drinking El Presidentes, shooting pool and just hanging out in general. The place has a "well-worn" look to it that fits like a comfortable old shoe...
If you are hungry, Dunbars also serves great burgers...try the Black & Blue Burger...
Barhopping in San Sebastian street in Old San Juan is a nice place to go meet locals. They have lots of places with pool tables there and on certain nights this narrow street gets inundated with the teenage and young adult crowd hoping to meet old friends. Nuyorican cafe is also good, it not on San Sebastian Street though...
It's a good place to get to see those old friends one hasn't seen in a while, and if youre a young tourist, a good place to hang out with the local crowd.
Dress Code: Not formal, some people go with t-shirts but obviously almost no one will wear shorts.
I enjoy cocktails at the Downstairs Bar
The Downstairs is a friendly laid-back place, with a regular clientele of locals and snowbirds (mostly men). It's a good way to meet Puerto Ricans on the hoof, so to speak.
Dress Code: very casual
Located here at that El San Juan Hotel & Casino is this beautiful, fantastic bar where you can enjoy a few Puerto Rican cocktails and chat up some very hot men!!