The Best Things to Do in Old San Juan (Approximately Top 10)


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Greetings, Internet Stranger, and welcome to the best things to do in Old San Juan. Pretty much any visitor to Puerto Rico wants to spend some time in Old San Juan. After all, it’s so picturesque and charming with its adorable cats and its colorful houses, and did I mention the cats?

But you don’t want to be just any tourist in San Juan! You want to be the kind of tourist who knows all the hidden secrets and goes places that locals go. Well, I’m no local, but with the help of a local guide and my total willingness to get completely lost in unfamiliar cities, I promise we’ll find the best things to do in Old San Juan together

Best Things to Do in Old San Juan

How To Get There

Now, I wish I knew where you lived, Internet Stranger, because I could send you a box of the finest rum. But sadly, I do not, and so I can’t tell you exactly how to get from your home to the Caribbean.

But I can tell you that I used a lovely airplane to get from my hometown NYC to London, and then I took a shorter flight to San Juan, Puerto Rico. I recommend Expedia for the best way to find the cheapest flight to the Caribbean at the best time of day.

You can even use Expedia to rent a car so you’ll be all set when you arrive at your destination. (I can’t drive, but if you can, this must be helpful.)

Just click here to start looking for the best possible deals on your flight, so you can head out to find the best things to do in Old San Juan ASAP.

best things to do in old san juan

Best Things to Do in Old San Juan

Where to Stay?

You are some lucky Internet Strangers because we have several choices for our best things to do in Old San Juan itinerary. And you don’t even necessarily need to stay in Old San Juan itself!

best things to do in old san juan

If you prefer relaxing on the beach, then a hotel in the Ocean Park neighborhood is for you! It will take a while to get to Old San Juan from here if there’s traffic, but if there isn’t, it’s just a short trip. One great choice in this area is the beautiful Andalucia House. The staff is extremely helpful, and the rooms are super cozy.

Or you could try the Dream Inn PR, which also has a great staff and a yummy breakfast included at the nearby Kasalta Bakery every morning. Does that hammock above look appealing? Then stay here!

best things to do in old san juan

You might think it’s easier to explore the best things to do in Old San Juan if you’re staying in Old San Juan. Then you can try the Decanter Hotel which has excellent rooms and a great location for an extremely reasonable price.

best things to do in old san juan

If you’d rather live in the lap of luxury, stay at El Convento, a famous luxury hotel with an adorable pet cat right in the heart of Old San Juan. It all depends on which neighborhood you prefer. And we’ll have a chance to check out both neighborhoods in this 24 hours in San Juan!

If The Decanter sounds great, and you like affordable and convenient hotels, click here. And if you are suspicious of all four of my suggestions and want to try something on your own, you can explore great deals on many other hotels in San Juan if you click here.

Best Things to Do in Old San Juan

What to Pack?

  • Shiny sandals because your toes will need to breathe while we explore the best things to do in Old San Juan.
  • An umbrella that’s tough enough to stand up to powerful Caribbean winds in case it starts raining while you explore the best things to do in Old San Juan.
  • A cell charger so that you don’t run out of power in your phone just as you’re about to take a picture of the gorgeous candy-colored buildings in Old San Juan.
  • A fabulous vintage swimsuit just in case you want to get in some beach time before heading to Old San Juan
  • A great spray sunscreen that will protect you from sunburn. It’s so easy to use, even a solo traveler can apply it to her back alone.
  • My favorite guidebook to Puerto Rico
  • One of the most fun ways to prep for a trip is to read a famous author from that country. Try the poetry of Julia de Burgos, a Puerto Rican icon. More people should read poetry for fun! Let’s work together to make it catch on!
  • I always travel with travel insurance from World Nomads. You never know when something might go wrong, especially in this day and age, and you don’t want to get stranded in a foreign country without help. You never know when extreme weather will strike or some other emergency. But with travel insurance, you’re protected even if you’re attacked by deranged sentient coconuts on your journey to find the best things to do in Old San Juan.
best things to do in old san juan

Best Things to Do in Old San Juan

Morning: Flavors of San Juan Food Tour

As I’ve mentioned many times on this blog, I am a huge believer in food tours. They combine fun facts with delicious eats. You satisfy your brain and your tummy at the same time. Everyone knows those are the two most useful parts of your body. So that means one of the best things to do in Old San Juan is definitely the Flavors of San Juan Food Tour. 

Our cheerful local guide introduced us to the many wonders of the local cuisine, all while showing us around Puerto Rico’s historic capital. I hope to convince you of the deliciousness of Puerto Rican food with…

best things to do in old san juan

Approximately top 5: Old San Juan food edition

1) Cafe Cuatro Sombras

The Flavors of Old San Juan Food Tour runs in both the morning and the afternoon. I had selected the morning food tour, so I was pleased to see the tour began with breakfast at a local cafe called Cafe Cuatro Sombras. Cuatro Sombras means Four Shades.

I guess you can have 4 shades of coffee? I never know what shade of coffee mine is because I’m a Philistine and get mine at Starbucks on the way to work. But I do appreciate great coffee when I’m able to find it.

san juan food tour

The coffee at Cuatro Sombras all comes from Puerto Rico, in the mountains of Yauco to the southwest. I was told that the coffee has notes of chocolate and caramel in it, and I could definitely taste it once they were pointed out.

And some day, I’ll be able to pick those notes out on my own! Even if I have to drink a cup of coffee every morning for the rest of my life, it’s going to happen! Some people really don’t like the taste of coffee, but I think that’s just because they’ve never had the good stuff.

For breakfast, we had a warm croissant sandwich with ham, provolone, and guava jelly because guava is extremely popular in Puerto Rico. Our guide told us that guava actually has more vitamin C than citrus fruits. I’m pretty sure that means I can eat all the guava candy I want and never catch cold again. That’s just science.

san juan food tour
2) senor paleta

Of course no breakfast is complete without dessert, so I was thrilled that we stopped for a paleta at the famous local paleta shop, Senor Paleta. Paletas are ice pops made with fresh fruit, and they sure are a treat on a sweltering morning in the Caribbean!

best things to do in old san juan

Senor Paleta is famous for its creative fruit flavors like strawberry mojito or passionfruit. You could really taste the flavors of the fresh mint and strawberry in every bite of the strawberry mojito. I’m not actually sure there was any rum in this pop though. I would probably need to eat about five more to be sure.

The best part about taking this food tour is that you get to skip the line for Senor Paleta, which usually snakes around the block. This alone is worth the price of admission.

best things to do in old san juan
3) The Parrot of Old San Juan

Our next stop was at a restaurant called The Parrot of Old San Juan. This place used to be a legendary spot called The Parrot Club, and I had actually eaten here the first time I came to Old San Juan back in 2011. It closed and has now reopened under new management and a slightly new name.

We got a little adventurous here with some fresh octopus ceviche. Ceviche is a raw fish dish where the fish is slightly cooked using citrus juice instead of heat. Our guide said the dish originally comes from South America, but it’s gotten to be very popular in San Juan, and no wonder! It’s an island; they can literally never run out of seafood.

The other dish on that plate is a warm and satisfying meat fritter called an alcapurria. I’ve been to Puerto Rico many times and I’ve never had an alcapurria before, but this is why we take food tours! You’ll always find at least one dish that’s new to you!

best things to do in old san juan
4) Make your own mofongo

We’d been snacking our way through the morning, so it was time for our main course! One of the most celebrated main dishes in Puerto Rican cuisine is the mofongo. This is a dish made by mashing plantains with a mortar and pestle, squishing the mash together with a glue made from garlic and butter, and then filling the whole mash with something delicious.

Our guide said mofongo showed the influence of the three main cultural groups in Puerto Rico. The indigenous population contributed the mortar and pestle, the Africans brought mashing plantains, and the Spanish threw in the garlic and butter.

My favorite part of the food tour was that we got to make our own mofongo! First you start with the plantains mixed with garlic and oil…Then you mash them up like you’re crushing the head of your greatest enemy. Next, choose a filling. We were given some mildly spicy chicken creole, which went very well with the starchy and garlicky mofongo.

Et voila! A finished mofongo! Your belly will be full and you’ll feel a pleasing sense of accomplishment. I told you this tour would be good for the brain and the belly. But it’s good for the arms as well.

best things to do in old san juan
5) Hecho en Casa

Now that we worked so hard to make our main course, it was time to reward ourselves with a second dessert. Hecho en Casa means “Homemade”, so you can probably guess that the restaurant specializes in locally made comfort food. We had a Barry White-level smooth flan made with coconut and cream cheese.

I had no idea that you could make flan with cream cheese, but apparently it’s quite common in Puerto Rico. This is a great choice for anyone who doesn’t like their desserts too sweet.

best things to do in old san juan

Best Things to Do in Old San Juan

Afternoon: Explore

Now that the food tour is over, it’s time for our adventure finding the best things to do in Old San Juan to continue. We’ll shop, we’ll stare at monuments, and we’ll go get freaked out my some elaborate graves. It’ll be the best. Let’s go!

Approximately Top 5: Best Things to Do in Old San Juan

best things to do in old san juan
1) Santa Maria Magdalena de Pazzis Cemetery

Whoo! That name is quite a mouthful. But visiting this cemetery is definitely one of the best things to do in Old San Juan. Many notable Puerto Ricans, including Oscar-winning actor and Mr. Rosemary Clooney himself, Jose Ferrer, are buried here. (Yes, that does make him George Clooney’s uncle. The world is a strange and small place.)

best things to do in old san juan

There are approximately one grillion amazing tombs to look at here, but my favorite sight was this family old small birds hiding in a groundskeepers closet. Who would expect to find something living and adorable in a cemetery? But as Jeff Goldblum says, “Life finds a way.”

Just keep in mind that if you are a pedestrian, it can be a little tricky to get into and out of the cemetery. I exited through a tunnel, but you need to go very slowly if you go through this tunnel, so you don’t get mooshed by an oncoming vehicle. Although, personally I think if you die trying to leave this cemetery, you should automatically get buried there.

best things to do in old san juan
2) Capitol Building

Puerto Rico isn’t an American state, it’s a US territory, which is a whole complicated issue that deserves an entire other blog post. But one thing it has in common with every state is that it has a capital city (San Juan) and a capitol building (this one above). In Spanish it’s called El Capitolio, but you probably didn’t need me to translate.

Technically, this building is just outside Old San Juan’s walls, but it’s within walking distance, so I’m putting it here anyway. DEAL WITH IT!

The building is sometimes open to the public, but it wasn’t when I was visiting because of a lot of protests about Wanda Vazquez Garcia, the then-governor of Puerto Rico. The previous governor, Ricardo Rossello, had resigned in a corruption scandal, so there had been a lot of protests around the capitol building going on for a long time. Hopefully when you visit, things will have quieted down and you can go for a tour.

The Best Things to Do in Old San Juan (Approximately Top 10) 1
3) Walkway of the Presidents

The Walkway of the Presidents has statues of nine of the ten US presidents who have visited Puerto Rico, all except for Donald Trump. (This is not a political statement; they are currently trying to raise money for the statue.) The Walkway is just outside the Capitolio, so it’s easy to visit when you’re done exploring the government building.

best things to do in old san juan

The first US president to visit Puerto Rico was Teddy Roosevelt himself. Each presidential statue has a plaque nearby explaining the president’s relationship to Puerto Rico. According to TR’s, when he visited San Juan, he announced that all Puerto Ricans should have US citizenship and declared the stunning El Yunque Rainforest nationally protected land.

That’s really not bad for a president who served over a century ago! Many modern presidents should strive to do as much for Puerto Rico.

best things to do in old san juan
4) Shopping!

All right, we’re back in Old San Juan proper, and we’re ready to shop til we drop! Shopping is definitely one of the best things to do in Old San Juan. But you don’t want me to steer you to any tourist traps, do you? Instead, let’s head to Artisan Corner, where you can pick up goods from the artists who make the crafts themselves.

I bought a lovely painting of a San Juan street scene from the artist himself. He uses a kind of Impressionist style that makes the image look flooded with sunshine. It just adds that perfect touch of cheerfulness to my wall.

My favorite food store in San Juan is Spicy Caribbee. I never miss the chance to buy their amazing hot sauce and banana jam.

If you want to support a good cause and be fashionable, get a bag from the boutique Concalma. The bags are sustainable, lovely, and made by local women. (The store also sells pretty jewelry and other fashion items.)

The Best Things to Do in Old San Juan (Approximately Top 10) 2

And if you want some more art, check out the work at Galeria Exodo. I bought a painting here by the daughter of one of the artists who was working there. It was of a cat, and the mama artist told me her daughter is obsessed with cats. But I liked the painting because San Juan is always covered by adorable stray cats, so now I’ll always think of San Juan when I look at it.

best things to do in old san juan
5) Cats of Old San Juan

And now we come to my favorite of all the best things to do in Old San Juan: the cats! Just roam around and see how many cats you can find. Can you see them all in this photo?

best things to do in old san juan

It’s like a Where’s Waldo of stray cats. There are so many cats in San Juan they even grow on bushes.

best things to do in old san juan

There’s a wonderful organization I’ve contributed to called Save a Gato. They neuter the cats to control the population. The organization also helps the cats get vaccinations and healthcare and even helps them find homes! Because so many cats live on National Park Service land (San Cristobal and El Morro), Save a Gato works with the NPS to help care for the kitties. Some of the cats even grow up to be night watch cats like this noble fellow.

best things to do in old san juan

The last time I was in Old San Juan, I started petting a friendly kitty with the back of my hand, and a mean old lady ran up to me and told me that the cat would give me a disease that was worse than the coronavirus. I’m here to tell you right now that this old lady was very wrong.

The Best Things to Do in Old San Juan (Approximately Top 10) 3

Best Things to Do in Old San Juan

Evening: Dinner at Restaurant 1919

OK, so we’re actually leaving Old San Juan for dinner and heading to 1919 Restaurant in the glamorous Condado neighborhood. But I say that one of the best things to do in Old San Juan is head to Condado for dinner, so it still counts.

1919 Restaurant is probably the most traditionally fine dining experience I’ve ever had in Old San Juan, but they use local ingredients, so it still feels like a Puerto Rican restaurant. I suggest getting the tasting menu so you can try as much as you can of what the restaurant has to offer.

best things to do in old san juan

The first course will probably be something light and refreshing like this heirloom carrot salad. Here’s what I have in my notes: Best carrots I’ve ever had!!!! I really want to know exactly what they put in these carrots to make them so delicious because while I like carrots under normal circumstances, they usually don’t warrant four exclamation marks.

best things to do in old san juan

Up next is the pasta course, and this one was stuffed with all kinds of seafood like lobster, shrimp, and calamari, plus a chorizo-like sausage called a longaniza. It was so rich and complex it was hard to believe it wasn’t the main course.

best things to do in old san juan

And yet here we have the main course: a lovely local Dorado fish served with tangy green tomatoes. It’s unusual to have a main course that’s lighter than the pasta course, but it worked perfectly here. Two rich courses in a row would have been gross.

best things to do in old san juan

And we finish off with a tropical dessert in the form of a lime pavlova made with graham cracker ice cream. It was almost like a deconstructed Key lime pie. But why can’t Key lime pie be an elegant dessert served as part of a tasting menu in a fine dining restaurant? I like a dessert that makes me think as well as satisfies my belly.

best things to do in old san juan

And Those Are the Best Things to Do in Old San Juan!

What do you think are the best things to do in Old San Juan? Are you ready to start booking your hotel in San Juan now? And what’s more dangerous, a kitten or coronavirus? Please leave your thoughts below!

Note: If you want to know how I put my travel itineraries together, just click here. Keep in mind that while each article is about how to spend 24 hours in a place, that doesn’t mean you should ONLY spend 24 hours with the best things to do in Old San Juan. If you have another 24 hours in San Juan, add this itinerary.

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