House Hunters Puerto Rico: Old San Juan, America’s Most Beautiful City


Old San Juan is part of the Despacito! TPOL Moves to Puerto Rico Trip Report. Catch up on the past episodes.

Do you like narrow cobbled streets? Do you love pretty, colorful buildings? Do you like history? Do you like bars? Do you like forts? Do you hate driving? Do you like walking to CVS and Burger King? If so, then move to America’s most beautiful city, Old San Juan. My first home when I moved to Puerto Rico two years ago was Old San Juan (see My First Airbnb Experience: Old San Juan). I lived there for two months and seriously considered buying a place there and not looking anywhere else.

Recall from the opening episode, House Hunters (Semi) International: Where to Live in Puerto Rico, my requirements were as follows, “Ideally, I would like to be close to city life, close to the ocean, and I would like to live on a golf course.”

Old San Juan checks off two/three boxes. Compared to lame Condado (see House Hunters Puerto Rico: Say No to Condado), Old San Juan has soul. While the bars are nothing special (see Where to Party Old San Juan: Best, Worst, Oldest, Grossest), it is fun to walk around and drop into random places, so long as it’s not the toilet at La Factoria.

Requirement 1: Satisfied

As far as the beach goes, Old San Juan is just a few paces away from Condado (see Running Hot: Where to Jog in Sunny San Juan), and a quick Uber ride to Ocean Park, another one of the options I considered (see House Hunters Puerto Rico: Ocean Park).

Requirement 2: Satisfied 

Which brings me to requirement 3, is there any golf near OSJ? There is not. And there is no convenient parking in OSJ. If you’re going to live within OSJ, be prepared to spend most of your time in OSJ. While it does have its charm, OSJ is very small. I could see buying a second apartment here but I could not make this my primary home.

Requirement 3: Not Satisfied 


Though I decided against living in OSJ, I like visiting the city and walking around. No matter how many times I go, I still end up taking pictures of the cobbled streets, the colorful homes, and the historical monuments. Here are some for your enjoyment:


  1. Very pretty. And to think, it paled before pre-Castro Habana vieja…now old Havana looks like a dumpster, and intermittently buildings fall apart

  2. The problem I see with OSJ is the price per foot. It seems VERY expensive (like NY/SF expensive), which greatly offsets the income tax savings.

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