back to top
Monday, July 22, 2024
HomeTrip DirectoryDespacito! TPOL Moves to Puerto RicoHouse Hunters Puerto Rico: Old San Juan, America's Most Beautiful City

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.a group of people standing in a street a can of beverage and a drink in a cup a building with a balcony and cars parked on the side of it

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).a stone building next to a body of water

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:

a cemetery with a body of water in the background a large grassy field with a statue on the side a white building with a flag on the front a white building with columns and palm treesa street with buildings and a street light a row of buildings with arched doors a street with buildings and a rainbow flag a brick alleyway with colorful buildings and treesa street with buildings and a stone wall a building with a palm tree in a pota stone street with buildings and a street in the background a row of cars parked on a cobblestone streeta street with cars parked on it a street with a row of buildings a narrow street with buildings and plants a street light in a narrow alleyway a brick road with colorful buildings a brick road with a red and white flag painted on it a building with a door and a balconycars parked cars on a street a sign on a wall a painting on a wall a wall with a painting of people a door with a star on it



  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.

Leave a Reply