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14 Things to do in Old San Juan (OSJ Scavenger Hunt)

You don’t really need this artle, or any Old San Juan scavenger hunt (or a popular things to do in Old San Juan list) to make the most out of the historic Caribbean city.

I can heartily agree that Old San Juan is full of things to do and see. It’s also walkable: there aren’t tons of cars and everything is pretty close by. Rental cars can’t be brought into OSJ (for good reason), so I recommend staying for 2-4 days at a hotel or Airbnb within Old San Juan. Just Uber from the airport to your lodging!

I like to take my time when visiting new places, but you might be able to find all these spots in a day if you’re in good shape and have good walking shoes. But I tend to linger around cool things and stand staring too long at artwork and architecture. If you’re like me, you’ll want to spend a few days in Old San Juan. Of our two weeks in Puerto Rico, we spent three days in the old city and probably could’ve stayed another day or two.

Tips to Enjoy Old San Juan

  1. Stay in Old San Juan. There are Airbnbs and Hotels in OSJ. You can’t even park a rental car in this part of San Juan (and thank goodness for that–it’s very walkable and safe in the streets) because of the old cobblestones roads and limited space. So you won’t be driving in and you’re not going to want to Uber (or walk) to Old San Juan–you’re going to want to stay there. Trust me. Plus, nearby Condado isn’t worth your time.
  2. Wear good walking shoes. My wife wears her adventurous Teva sandals no matter how much walking we’ve got on the agenda, but I sometimes opt for a pair of running shoes, like Brooks. Her Tevas are nice and breezy, but my Brooks give a bit more cushion. Old San Juan is very walkable. Our moderately-priced Airbnb was less than a 5 minute walk to some of the city’s most famous sites.
  3. Bring a hat, sunglasses, and sunscreen. The Puerto Rican sun gets hot! Slap some sunscreen on before you head out the door and don’t forget a hat and sunglasses. I found myself regularly seeking shade while strolling through OSJ.
  4. Scavenger hunts are fun, but… don’t be afraid to simply wander and find things on your own. If you’re in Old San Juan for a few days, walk around and find things that look interesting. If you spend all day out of your hotel, you’ll be sure to hit all the good spots. We didn’t plan much (except this walking tour ⭐⭐⭐⭐⭐) and loved our time there.

Some of the many cheerful colors of Old San Juan.

1. Barrachina: the home of the original piña colada

Look for the big, historic plaque that marks the spot where the famous piña colada was first crafted. While you’re there, have a piña colada (make it virgin if you’re with kids)! I’m a big piña colada guy, so this was cool to see.

Apple Maps | Google Maps

2. Multicolored buildings: find an orange house

Did you know buildings in Old San Juan aren’t allowed to be painted the same colors in a row? How many colors can you find? Take a picture with an orange house, restaurant, or shop in Old San Juan. I like the color orange because I like sunsets, but pick another color if you’d like! Or, see if you can photograph the entire rainbow while you’re staying in Old San Juan.

You won’t need a location tip to find some colorful buildings. Just walk outside and look around you.

3. Find a cannon at the Spanish forts

Cannons abound in this old Spanish city, especially in two obvious places: Castillo San Felipe del Morro and Castillo de San Cristóbal, immense and fascinating sea-facing forts. There are cannons, dungeons, and towering walls from which Spanish soldiers would watch for enemy ships. If you enjoy history, you’ll be glad to check out these forts. If not, you’ll enjoy the incredible views offered from the forts’ walls.

Castillo San Felipe del Morro: Apple Maps | Google Maps
Castillo de San Cristóbal: Apple Maps | Google Maps

4. Pose in a sentry tower, too

While you’re perusing the cannons, stop in a sentry tower overlooking the sea. These castle-like towers are historic lookouts for enemy ships (and later, planes). They’re tiny little rooms along the city’s old walls that make for excellent photos.

Castillo San Felipe del Morro: Apple Maps | Google Maps
Castillo de San Cristóbal: Apple Maps | Google Maps

The forts and walls of Old San Juan are dotted with sentry towers (first) and gaps for observing and repelling enemies (second).

5. The tomb of Juan Ponce de León

Named the first Governor of Puerto Rico by the Spanish crown in 1508, Ponce de León explored and charted much of the Caribbean, becoming quite wealthy through the usual brutal colonial tactics. He is an important figure in the known history of Puerto Rico and greater Hispaniola.

Ponce de León’s final resting place is in Puerto Rico’s oldest cathedral, which is free to enter and quite photogenic.

Apple Maps | Google Maps

6. Descend into a crypt

To get your picture, you’ll need to go down the steps to stand amongst the tombs. Did you know many people in Spanish colonies (like Puerto Rico) were buried beneath the floors of churches? Eventually they put them in the walls. When you’re walking around Puerto Rico, there are dead bodies probably buried everywhere (probably).

Andy, our fantastic tour guide, showed us into a church’s old crypt.

Parroquia San Francisco de Asis: Apple Maps | Google Maps

7. Take your picture with Fortaleza Street

You can’t miss it! But right now, you also can’t walk on it. Calle Fortaleza (Fortaleza Street) stretches toward the Governor’s Mansion and it’s been closed for quite some time due to protests and insecurity. While you cannot walk down the road toward the Governor’s Mansion, you can do like every other tourist and take a photo at the barricade with the famous hanging umbrellas in the background. You’ll probably have to wait in a short line for your chance to snap a picture.

While you wait, the best gelato in the world is on the corner. You’ll know it when you see it.

Apple Maps | Google Maps

8. Anita La Mamma Del Gelato

Speaking of that gelato, let’s add it to our Old San Juan scavenger hunt. There’s always a line, but it’s worth waiting. You’ll be amazed at the number of flavors (including vegan options) they have, if you’ve never been to another of their locations all over the world. We visited more than once while hanging out in Old San Juan.

Apple Maps | Google Maps

9. The many stained glass windows of Old San Juan

And I don’t mean from the outside! Duck into a church, take in the architecture, and find a pretty stained glass window. The older churches (there are a few that are super old) will make you say “ooo” and “ahh.”

This is another you probably don’t need a location tip for. Duck into any Catholic church you see (all over Puerto Rico, really), and you’ll be impressed.

The churches in OSJ are some of the oldest in North America.

10. La Rogativa sculpture

Overlooking the sea–one of the best views in Old San Juan–is a bronze sculpture of torch-bearing women and a priest. Legend has it in 1797 the English Armada was preparing to invade San Juan. However, a religious procession of women carrying torches looked like military reinforcements from afar, and the mighty navy stood down.

Apple Maps | Google Maps

11. Kitties

Certain areas of Old San Juan (the quieter areas, we noticed) abounded with friendly stray cats. I think we even passed a cat rescue and sanctuary. Adopt a street kitty into your scavenger hunt: take a picture with your favorite. Note: never pick up a stray cat, but show them some love from a few paces away.

12. The San Juan Gate

This imposing red gate was once the official entrance to San Juan. Do you feel important walking through it? Are you transported to another time? Outside this historic passageway is a lovely recreation trail around the city’s walls.

Apple Maps | Google Maps

13. Capilla del Cristo

This 18th century, tiny chapel is perched on the city’s towering walls and is in near original condition. It’s free to visit and quite lovely.

Apple Maps | Google Maps

14. Casa Blanca

Old San Juan’s oldest residence was originally built for its first governor, Juan Ponce de León. It has lovely grounds that are free to roam while the building itself now serves as a museum.

Apple Maps | Google Maps

There you have it. Those are 14 things to do and look for in Old San Juan. You’ll mostly read and hear about the forts, food, and blue cobblestones–and for good reason, I suppose. However, just wander. I really believe that three days of wandering Old San Juan is time well-spent, and you’ll stumble into everything.

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George Callahan is the creator of Pine Tree Poet. He is an author of fantasy stories and an adventure poet. He prefers mountains and pine trees to most other things, and usually takes his dog Cowboy along for the ride.

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