I’m a single 28 years old guy who travels a lot for business. I consider myself a pretty social guy and hands-on executive, but I was a little nervous when my brother suggested I go bar hopping with two of his friends that currently live in Puerto Rico.

by My Puerto Rico Experience

I had never been to Puerto Rico before so I had to ask where could I take my boss to dinner and my brother’s friends said a good business/pleasure hotel in San Juan was La Concha. So we went to Komakai Sushi Bar, one of La Concha’s restaurants. My boss wanted to go over the deal we had just closed and next steps. They were right. The sushi was extremely fresh and delicious, and the lobby’s atmosphere was perfect to talk business.

We moved to the bar, to check out the cocktail menu and I was impressed. I particularly enjoyed their Single Malts, Glenfiddich variety. The staff was courteous and caring too, which made the meeting go even smoother.

My boss and I parted ways around 9pm and I hailed a cab to El Bar Bero to meet my brother’s friends. They were super nice and kept calling me “Baby Bro”. One of them passed me a Tiki Man, whatever that was, it was INSANE. Then I ordered a gin and cucumber drink called “El Bigote de Luigi” (Luigi’s Mustache), creative and perfect. The bartender –his name is Carlos- was eager to explain every drink and the process behind their confection. I will definitely come back to this place next time I’m in Puerto Rico. I noticed that there’s a Doubletree by Hilton hotel just around the corner so I could just roll from the bar to the hotel if needed.

I left with them to visit, La Placita? When we got there it felt like we had gone back in time. It kind of reminds me of movies from La Havana, Cuba in the 1950s. The buildings were old but well kept, and there was music and people dancing everywhere. I had some fish tacos to handle the rum to come and they were good. It was at a barbeque joint, I can’t recall the name. At 11pm the place was flooded with people. I felt a bit overdressed but was too drunk to care. We had mojitos, watermelon sangria, beers, more pinchos… Can’t even remember everything we drank and ate.

I practiced my terrible Spanish and danced awkwardly with several girls that my brother’s friends knew. The best part of hanging out in Puerto Rico? How effortless it was to make friends and have fun.

Somehow we ended up in Old San Juan at 3 in the morning at this place called El Batey. It was a “Rum Diaries” kind of joint. No class. Graffiti-covered walls. Super cheap. Well known as a dive bar. When we came out of there to leave Old San Juan, the sun was coming out and we were still hanging out with lovely ladies. What more can a guy ask for?