The ins and outs of living in Puerto Rico

Living in Old San Juan


Picture source and all credits to:

Picture source and all credits to:

So when people ask me where to live in San Juan, I normally recommend the Condado or Isla Verde areas, especially if they are on the younger side or really like the city-like walkable feel. But what about Old San Juan!? Is living in Old San Juan a good option? It is, and it is not, read the following:

All in all, Old San Juan is quite nice with a lot of personality, beautiful cobblestone streets dating back to the 16th and 17th centuries, amazing restaurants, home to my all-time favorite coffee shop in “Cuatro Sombras”, it also has some other amazing coffee shops, it’s the birthplace of the Piña Colada, there’s lots going on, you can walk just about everywhere and also get just about everything you need, all in one *small* community rich in history and character. Why not move there right? I admit, I know a couple of people who either live or have lived in Old San Juan, and in one occasion I went to a friend’s apartment there and I just loved it. I loved the simplicity, I loved how old and historic the apartment building felt, I loved the tiny balcony with a view of the bay of San Juan where 2 cruise ships were docked at the moment. I really loved the entire feel of it, but that’s where it ended for me, I felt that realistically, for me, Old San Juan (OSJ) was not really an option, I’ll explain why.

First, there are too many people, especially in peak cruise-ship tourism time (November through April). Thousands and thousands of people flock swarm OSJ when their ship docks to do all kinds of shopping and eating, add to that the thousands of Taxi cabs present and people jaywalking. If you are walking, then it is not a big deal, but driving on that to get to work or to get home is very hectic and slow with so many people around. Granted, this is mainly a problem close to where the ships are, so further up and close to El Morro the problem is not quite as bad. However, those areas do get quite crowded when there’s a movie being filmed (which is more often than you’d think), driving through that and finding parking can be a nightmare.

Second, it is, well, old. As much as I loved my friend’s apartment and how historic and simple it felt, there was no parking nearby and if you wanted to park you’d have to pay. Not a problem for those without a car, but I (and most families) have at least one car. In addition, there was no A/C! When I saw the apartment it was during winter break from college so it wasn’t that hot, but I can’t even imagine how hot it would be in there in the summer months, sleeping while sweating is not something I care to do very often. Oh did I mention no elevator? The apartment was 5 floors up, no elevator, great exercise, but bringing groceries up or if you have small children, those 5 floors might be a problem, something to think about.

There are however some newer apartments in the area but they are in the outskirts of OSJ, which means that you would have to walk a ways (with some very decent hills) to get to where the good stuff is such as the birthplace of the Piña Colada or El Morro to fly kites, not too far from the Cuatro Sombras coffee shop or some of the really tasty restaurants though.

Not particularly family friendly, again, there is lots going on, and not all of it is family friendly (which may not a problem if you are single or a young couple with no plans of having kids). For example, the “Fiestas de la Calle San Sebastián” are celebrated in January each year for an entire weekend, it’s a huge party and LOTS of fun, full of music, artisan shopping and hanging out with friends outside, it truly is fun. But what’s the aftermath? If you go early in the mornings following the night’s party, you will find lots of trash, drug paraphernalia, condoms, underwear, and in occasions, people passed out on the streets. So it’s fun to go to the party then leave, but living in that is something I particularly don’t care to do if I have a family, or a job and I have to work the next day! =)

Only one real option for a beach. Unlike Isla Verde, which has a long line of beautiful beaches, and Condado which has a beach at each end plus a few small beaches in between; Old San Juan has only “El Escambrón” which is actually nice but it is just outside of OSJ and it can be quite a long walk.

So there it is! I’m sure I missed a few good and bad things about OSJ but those are the main things I think about when I think about living in Old San Juan. What do you think? I hope you find thins post helpful!





Author: Jay-Webmaster

Jay is an Atmospheric Physicist and Massage Therapist who was born and raised in Puerto Rico but went to college in the US before moving back to Puerto Rico. Creator of and the new forum


  1. Hello Jay, love your blogs, they’re very helpful. I want to ask you a question about car shipping to Puerto Rico. Anything you might know would be of great help.
    Would I be able to ship a car I still owe money on?

    • Jay-Webmaster

      Hello Christian!

      Thank you for the nice words!

      Well, when it comes to ship the car that you still owe money on it really depends on your financing company. In my case, I had my car financed through Toyota Financial, and there is a Toyota Financial here in PR so with a letter from my employer confirming that I am moving to PR because of a job and the fact that Toyota Financial is present in PR, I was able to move my car even though I still owed money on it.

      You would have to contact your bank and see, but in most cases I have heard that people pay the car off before moving.

      Take Care!

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