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Date Night in Old San Juan, Puerto Rico

  • Oct 18, 2018
  • 4 min read

In or going to San Juan Viejo (old) in Puerto Rico and trying to figure out what to do? I'm here to help! A few days ago, I found myself in the same predicament and I knew my main objectives were to be safe, try authentic Puerto Rican food and Salsa dance. During the day, you can do the beach and the historical stuff but moving into the night is another story.

As always, above and beyond anything else, the highest priority is to stay safe. I used this Neighborhood Safety Map, in addition to Hotels.com, to help choose where to stay and know where we could go so we could walk at night without worry. (We stayed on Calle Fortaleza.)

Once that was done, it was time for the fun stuff!

We were hungry by the time we arrived and checked in so we headed for the closest, neat-looking food place we could find. Just a few blocks downhill from Calle Fortaleza we found a series of trendy restaurants and decided on La Cueva Del Mar. Our waitress informed us it is one of several popular restaurants by the same owner. The atmosphere was good and they have several Happy Hour food and drink specials. They were cranking out the 2 for $5 fish tacos so we had to try them. We tried the Creole Seafood Mofongo too, a traditional Puerto Rican dish with Afro-Carribean/Latin influences, a must try when visiting Puerto Rico. Anywhere you go Mofongo seems to take a long time to cook so order appetizers if you're really hungry! The fish tacos worked out perfect for us while waiting on the Mofongo. Our waitress was extremely nice and gave us her recommendations for the best things to do for the rest of the evening.

From La Cueva Del Mar, we headed back up the hill on Calle de la Tanca and popped in to Smoke It to try some Puerto Rican Rum and he tried a cigar from their humidor room. Puerto Rico makes their own rum and being the (self-proclaimed) rum connoisseurs we are, we wanted to try their best. We were recommended the Don Q (9-12 year) and the Ron de Barilito, not bad! I preferred the Don Q.

As recommended, we continued up the hill, through the plaza, then straight up, up a little more, we headed for live music just across from the ocean at Callejon de la Tanca. We were just starting to wonder if we were walking the right way when we heard the music. The band was fantastic! Outdoor music with the ocean breeze.. now we were getting somewhere! It was pretty crowded for the small area so we posted up on the neighboring Las Palmas restaurant patio. We could still hear the music just fine and decided to have some Shrimp with Crema de Coco (coconut cream sauce), delicious! Once again served with Mofongo but distinctly different than the Mofongo at La Cueva Del Mar.

Callejon de la Tanca was a little too crowded to really get any dancing done so our mission continued. We had a little time to kill here and there until we made it a few blocks away to La Factoria on Calle San Sebastian, our grande finale for the evening. ("Calle" = "Street" in spanish by the way) La Factoria is a local hipster speak easy with trendy cocktails, small plates and tattooed bartenders. This is the sort of place that makes you feel like you're in the know. It is a multiple level building and they open the upper levels the later it gets into the evening. Since salsa was our objective, we were interested in the second level which opened around 10 pm with a great local band. We slipped through the swinging saloon doors, to get into the extremely crowded space where it was all happening. If you can't take a small crowded space, this is not the spot for you; but, if you want some down home, sweaty, authentic Puerto Rican salsa, put your hair in a ponytail, leave your purse at the hotel and get ready to squeeze into the mix. It was still rockin' at 2 am when we decided to drag our sweaty, tired butts back to the hotel. Even that late, we walked back without any problems.

Safe, fun, authentic food, and a sweaty salsa sesh = Mission accomplished!

By the way, if you are traveling from the airport and wondering about an airport transfer, you will find there is only one taxi service available from Luis Munoz Marin International Airport. Follow the signs to exit the airport to ground transportation and there you will find a line for the official Puerto Rico Tourism Taxi service. The prices are set and the cars are nice. It cost $23 for two people with one bag to go to Old San Juan. Once you get there you can walk everywhere pretty much. Going back to the airport I used Uber for about $10. (Uber is not allowed to pick up from the airport.)

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