A Local’s Take of the Best of Old San Juan, PR

Luis Peña Crescioni
Jan 4, 2021
17 min read

Updated: May 16, 2023

I promise you this will be your best guide when visiting my amazing island!

Forget about that typical touristy TripAdvisor app! I will give you the local tips, great fun facts and even make you laugh while you are it.

Some of the pictures I have taken in Old San Juan

Note: Click on any section link to quickly go to your desired place.

Section I: A Little Bit About Me

Section II: Puerto Rico's Historical Background

Section III: My Local To-Do List in Old San Juan

Section IV: My Top Restaurants in Old San Juan

Section V: Hang Out Like a Local in Old San Juan

Section VI: Best Waterfalls / Rivers / Caves in Puerto Rico

Section VII: Best Beaches in Puerto Rico

I. A Little Bit About Me

I was born and raised in San Juan, Puerto Rico. I have been living in Old San Juan for many years and I can say it is one of my favorite places in the world! There's something very magical about having this beautiful colonial Spanish city surrounded by ocean water.

Having the pleasure of walking every street and corner of "El Viejo San Juan", I decided to create this guide. Throughout the years, I have been sending my recommendations to all my friends that come and visit from around the world. After sharing and giving them many tours, I received great responses. Then I thought, why not share it with the rest of the world?

My wish is that you fall in love with Puerto Rico the same way I did. By spending your time as efficiently as possible doing the absolute best things in a more fun and local way. I will also share with you my list of the best restaurants, bars, things to-do, beaches and waterfalls. It's nice and convenient because you can see all the locations easily in a map format without having to search anything.

Feel free to Follow me on Instagram: @Backpackingluis and ask me any question about Puerto Rico :)

II. Puerto Rico Historical Background:

Note: If you are in a hurry and want to skip the history just go directly to Section III.

Fun fact about me: every time I visit a new country I deeply learn about its history. It makes it more interesting and fun when you have this historical knowledge and then actually experience it. So, I will try to give you the "boring stuff" with the cool local fun facts. All this for you to have a more authentic experience.

First encounter of the Spanish with the Taínos, photo by Abdul Rob

Puerto Rico translates as "rich port", because its San Juan port had an excellent location and abundance in resources. It was "found" by the Spanish in 1493 . I say found because it surely was not discovered by Columbus, this is something I personally think that the history books should change. The first name placed by the spanish was San Juan Bautista island and they later named the whole island to Puerto Rico. Before the Spanish invaded the island the Taíno, our local indigenous people, lived peacefully and called their native island "Borinquén". This is why many Puerto Ricans very often scream out "Yo Soy Boriqua, pa' que tú lo sepas!", saying that they are proud "Borinqueños".

Proud Puerto Rican, gif by intoactionus

Columbus first came in thought the west side in the town known as Aguada. Later in 1508 the first settlement, Caparra, was established by Juan Ponce de Leon in San Juan —remember that crazy old guy looking for the fountain of youth in the pirates of the caribbean movie... that is Juan Ponce de Leon?— and later in 1521 Old San Juan begun to be built. Many of the taíno population was killed in battle or wiped out due to new diseases the Spanish brought like Smallpox. For this reason, the Spanish brought in enslaved Africans to do all the hard work. (This is why there isn't a particular skin color for Puerto Ricans.) You will see many grades of skin shades, from lighter tones to darker ones. Usually a "medium" shade of light-dark called trigeño is more common.

We are almost done with the quick history... I promise!

A Jíbaro cutting sugar cane, photo by mashable

From the 16th-19th century, Puerto Rico was booming economically due to sugar cane, coffee and tobacco production. It also presented a major military advantage because whomever held it had the keys to the Caribbean, it was the first large port stop. For this reason, we were invaded by four rivals of the Spaniards. In 1528, the French attacked the west of the island. The first attack by England was in 1595 by Sir Francis Drake and John Hawkins which failed. Later, in 1598, the British with Sir George Clifford conquered and ruled Puerto Rico for two months!

In 1625, the Dutch took control and burned down the capital. Interesting to me: I could have been speaking French or even Dutch right now, but due to history that is not the case. In 1797 the never surrendering Brits, with General Ralph Abercrombie and Admiral Sir Henry Harvey, tried their last attempt to conquer our beautiful island and guess what? They failed...

1625 Dutch Invasion in Old San Juan

In 1898, the United States, with all their fancy new ships, invaded Puerto Rico and took control of the new island which they named Porto Rico. They raised the US flag and quickly changed the official language to English. Nowadays this is not the case, we were re-named Puerto Rico and our official languages is Spanish since 1932. A large part of the population learns English as a second language.

Calle Fortaleza in Old San Juan 1938, photo by Grace Arroyo

Click Here if you want to see more old pictures of Old San Juan

From the 20th-21st century there has been a lot of history regarding politics, but because this is not the main focus of this blog, I will not get into it that much. Puerto Ricans became US citizens in 1917 due to US needing extra troops in World War 1 with the Jones Act. In 1952 our commonwealth was established (Estado Libre Asociado) and our beautiful Puerto Rican flag was officially adopted. This constitution, is what we still have today. We are neither a US state nor an independent country, we are a US territory. In other words, one of the last colonies of the world. Yes, we also use the US currency!

Maria Paula dancing typical Bomba music, photo by Viviana Del Valle

Overall, we are very charming people who have a lot of energy and enjoy life in our all-year-round warm Caribbean waters. We have a lot of passion for music and love to dance everything, especially dancing some of our typical music like Salsa, Merengue, Bomba and Reggaeton! The majority of Puerto Ricans release their stress by getting a lot Vitamin-Sea. Our best medication is to spend a day swimming our crystal-clear beaches or in our beautiful caves and waterfalls in the inner parts of the island. I will be sharing all my lists with my secret beaches, caves and waterfalls at the end of this post, so stay tuned!

III. My Local To-Do List In Old San Juan:

Note: These are my personal recommendations, it's what I have been doing for many years and think is best. You can program the order how is best for you, but if done on my order it works perfectly well because it has a logical route and adequate timing to have your meals. It can all be done in one day if you start early at 7 am-8 am or divide it into a few days for a slower pace. Or if not, do it however work best for you. In this case, like I always say: "go with the flow".

Also, look up everything in google before to make sure it is open due to COVID-19 Restrictions. I have attached Google links for each place.

1. Start With an Amazing Breakfast at La Carreta Restaurant:

Enjoying some amazing pancakes with fruits & a mimosa, photo by tastingpr

This beautiful restaurant is on my local favorites! They have an amazing breakfast/brunch menu. Try the stuffed cream French toasts or the great variety of egg omelets. The coffee is local and it is really good! If you are vegan/vegetarian go for the avocado toast and get extra fruit. If you want to start having fun early get the bottomless mimosas— it would make you laugh more during your Old San Juan tour! If you don’t drink well stay extra hydrated with water, it would be a long walk today.

Click Here for the Google Maps location

Click Here to see La Carreta's menu & more pictures in Yelp

Note: They open at 8:00 am, try to get at this time so you can have time for the rest!

2. Time Travel to the Past by Visiting the San Cristobal Fortress ⚔:

San Cristobal Fortress view from the air

A quick walk from La Carreta restaurant and you are in the biggest fortress in the Americas! This Spanish fortress was built around the 17th century. I usually like to start here because when you are on the top fort you can see the city well. It is always good to have a better perspective of the city by looking from higher ground. I recommend it due to being very interactive, having nice history expositions, having cool tunnels and amazing ocean views.

Click Here for the Google Maps location

Click Here for more historical background

Recommended Visit Time: 1 hour

Hours of Operation: 9 am-6 pm

Price: $10 Adults and Children under 15 FREE

3. Fly a Kite in the Beautiful Landscape of El Morro:

Flying kites and view of el Morro

Flying a kite, or chiringa, is a very traditional thing to do for all Puerto Ricans in this paradise. Therefore, you should experience this even if you are an adult, we all have an inner child hiding somewhere! There is usually a man that sells kites on the corner near the Totem Plaza, ask him for a chiringa. Enjoy the view!

Click Here for the Google Maps location

Click Here for more historical background of El Morro

Price: Around $5-$10 a kite

4. If you are into Museums I recommend the Museo de las Américas:

Inside the museum, photo by Museo de Las Americas PR

If you are not into museums well you can skip this, but I think is a great place to learn even more about the Puerto Rican culture in order to have a more authentic trip. If you only have one day, you can just skip this so you will have time to do everything else. If you read the PR background on Section II, you would get a better feeling by seeing it in person. The museum has great expositions from our indigenous Tainos, the Spanish, the Africans and today's modern civilizations. Also, the museum is inside an amazing plaza called Cuartel de Ballajá.

Click Here for the Google Maps location

Click Here for more historical background of Cuartel de Ballajá

Recommended Visit Time: 1 hour

Hours of Operation: 11 am- 4 pm (Open from Thursday-Saturday)

Price: $8 Adults. Children under 12, Students & Seniors +65 : $6

5. Try a "Piragua":

Typical wooden piragua car, photo by me

This is another traditional thing locals do when visiting Old San Juan. You choose from many flavors and pour them in a ice snow cone. It's a great refreshing treat for a hot day. There is usually one in between the Totem and the San Sebastian street. If not ask someone for the closest one because it is very typical.

Click Here for the Google Maps Exact piraguero location

Click Here for more historical background of la piragua

Price: Around $2-$3 each

6. Take a Picture in El Totem:

El Totem from viewed from down to up

This work of art was created for the 500-centennial celebration since Columbus' arrival. It symbolizes our native indians you should know by now... the Tainos! Also, try to find the the lamb statue with the flag, it symbolizes our Coat of Arms.

Legend says... if you climb it you become a Taino. No, I'm kidding! I heard that back in the days, drunk people used to climb it and that is why it has a black slippery bottom so you don't even think about this ridiculous idea that I would totally do.

Click Here for the Google Maps location

Click Here for more historical background about El Totem

Price: Free

7. Take Stunning Pictures at Casa Blanca:

Inside Casa Blanca

It is the first fort built in Puerto Rico in 1521, made for the first governor, Juan Ponce de León — the crazy old fountain guy. This place has a beautiful white color than makes a great contrast if you have some nice colored clothing. It usually has some free expositions in one of the first rooms. It also has a small museum and stunning views from the top.

Click Here for the Google Maps location

Click Here for more historical background

Hours of Operation: 8:00 am- 12:00pm & 1:00pm-4:00pm (Tuesday-Sunday)

Price: Free

8. Get Lunch at Calle del Cristo:

People eating in the la Calle del Cristo, photo by me

There are a few restaurants right outside in the middle of the street, I recommend La Danza Restaurant. Try a nice local plate of arroz con habichuelas, tostones or amarillos and your choice of seafood/ meat/ chicken/ veggies. Get a Medalla (our local beer) or a mojito made with Don Q (our local rum). If you don't drink alcohol, get a virgin mojito, no excuses!

Click Here for the Google Maps location of Calle Cristo

Click Here for the Google Maps location of La Danza restaurant

Click Here for the menu of La Danza restaurant

Note: If you want a different restaurant, Go to Section IV to see my entire Google list of my favorite restaurants

9. Take the Typical Umbrellas/Flag Picture in La Fortaleza:

La Fortaleza in the back and the hanging PR flag

I think this has become a major tourist attraction. Go ahead and take your sexy, holding your breath, picture here. Every often they change exposition. Currently there is a huge Puerto Rican flag! Click Here if you want to learn more about the Puerto Rican flag.

This fortress was built around the 1530s and it is were the current governor lives. This street has a lot of history, one major event happened here a little while ago. Search in google this: July 2019 Puerto Rico and look for pictures, history was made. If you're interested in seeing some political past, then Click Here and also ask locals how it was like. If not, just keep enjoying your day!

Click Here for the Google Maps location of the umbrella/flag street

Click Here for more historical background of La Fortaleza

Price: Free for pictures outside :)

Note: If you are interested, there are tours to go inside la Fortaleza, Click Here

10. Visit la Capilla de San Cristo:

La Capilla de San Cristo

This cute small chapel was built around 1753-1780. It was built due to a miracle! Try to find a brown plaque that explains this. Or if you end up being very bad at finding this... just Click Here.

Click Here for the Google Maps location

Click Here for more historical background of the miracle

Price: Donation if you want to go inside, if open.

11. Get Some Pigeon 💩 at Parque las Palomas:

@Nina_aventurera hanging with her pigeon friends at Parque las Palomas

Yes, you heard me loud and clear. Buy some corn and feed the pigeons. You would then be lucky if they bullseyes you! Locals say that if you get that gorgeous gift you are more in luck to win the lottery. So, go quickly and play "La Loto" or the "Lotería de Puerto Rico" that are usually sold in the streets. If you win, send me a gift via Venmo or Paypal, thanks! Also, grab a quick coffee in Cafe Del Niño. Their view is amazing and 100% Puertorican coffee.

Click Here for the Google Maps location

Click Here for more historical background

Hours of operation: 9:00 am- 5:00 pm

Price: They actually pay you millions here

12. Visit and Take Pictures with the Smallest Apartment in Latin America:

Smallest apartment in the Americas with the PR flag

It is a cute tiny yellow apartment facing the harbor. On weekends there is usually live music in one of the restaurants near here.

Click Here for the Google Maps location

Click Here to see it is on the top smallest houses in the world

Price: Free picture :)

13. Cool off by eating a local Señor Paleta natural ice popsicle:

@Nina_aventurera enjoying her favorite popsicle,

They have many flavors from natural fruits to that Nutella popsicle you always crave on. You can add many toppings too. Enjoy it with the view of the bay there in a small plaza in front of this place. They also have popsicles for your pets!

Click Here for the Google Maps location

Click Here to see their menu

Hours of Operation: 10:30 am -10:00 pm

14. Visit La Perla:

The colorful houses of La Perla. Right in front of the Atlantic Ocean

La Perla got famous a few years ago because it is the location where they filmed the "Despacito" music video— the most viewed YouTube video in the world, after that annoying baby shark video. If you have not seen it yet Click Here. It would give you a good background view of la Perla and our crazy sexy Latino dance moves.

La Perla is a small community in front of the historical walls and the ocean. It is safe, but I recommend it to people who really like adventures. The community is low in resources and may not be appealing for some. I try to be honest because I know there are many different types of travelers.

If you are in for the adventure go during the day and maybe rent a Scooter to tour it and ride it around old San Juan. Also go to the bowl of la Perla. On the weekends it is nice because the locals fill up the pool and there are some nice local beachfront bars with good Puerto Rican music so you can dance!

My friends and I hanging out the La Perla Bowl front beach pool

Click Here for the Google Maps location of la Perla

Click Here for the Google Maps location of la Perla Pool Bowl and front beach bar deck

Click Here for More historical background of la Perla

Another thing I recommend in la Perla is to visit la Garita del Diablo, an important sentry box for the Spaniards. It is about a 10 minute walk to it; you must go down through some stair and then walk through the rocky beach to get there. It has a haunted legend you should read about here.

La Garita del Diablo viewed from the air

Click Here for the Google Maps location of the stair that gets yo to La Garita del Diablo

Click Here for the Google Maps exact location of La Garita del Diablo

Price: Free

Last thing is to eat at la Garita de Yaz restaurant and go outside where it has a scenic ocean view. See #15 in my list to make sure you order the best PR dish.

Click Here for the Google Maps location of la Garita Restaurant

15. Try our Best Local Dish: Mofongo Relleno!:

I have had friends that have fallen so deeply in love with this dish, that they ate it three times a day during their visit! But if you are in a diet... well you are in vacation mode, so no strict rules!

A nice view with an amazing mofongo with rice & beans in Patio de Sam

If you went to La Garita de Yaz restaurant well I hope you ordered a nice mofongo and enjoyed that amazing view. Other places I highly recommend having the best mofongo are: Ajo del País, has cool vintage PR items, Punto de Vista Rooftop, has an amazing city view, and Puerto Criollo, has a nice outdoor seating near Plaza Colon. In Section IV, I have attached my personal best Old San Juan restaurants, go check it out too if you want something different or have more days in Old San Juan.

Click Here for more historical background of the mofongo dish

Mofongo Price: Varies around $10-$25, it fills you up well

16. Try a Few or a Lot of Piña 🍍 Coladas 🥥 in Barrachina:

Enjoying a piña colada in the Barrachina center plaza

The official birthplace of the best drink of the world, la piña colada, is in Puerto Rico since 1954! It is our national drink since 1978. They have an official plate that states it was invented in the Barrachina restaurant, but others says it was invented in the Hotel Caribe Hilton. Who cares, just drink up and chill! If you don't drink alcohol get the virgin one with extra cherries. Again, no excuses!

Click Here for the Google Maps location of Barrachina

Click Here for more historical background about who really invented this amazing drink

Hours of Operation: 7:00 am - 10:00 am

Price: Around $5-$8

17. See the Sunset in My Secret Local Spot Next to El Castillo San Felipe del Morro:

Best place to see this beautiful sunset next to Castillo San Felipe

Be sure to arrive around 15 minutes before sunset, usually between 5:00pm-7:00pm, Click Here to find out sunset hours. This place is right next to the fort and I promise you it has the best view! Just sit back and relax to the beautiful and colorful show. From here you can also see El Cañuelo, if you are into more history Click Here.

Click Here for the Google Maps coordinates of the ladder you have to go down. Then walk the left facing the castle until you reach the end.

Click Here for the Google Maps coordinate of the best view in the world

A note here, if you have time for another day in Old San Juan, plan a visit to el Castillo San Felipe del Morro. I prefer el San Cristobal Castle, that is why it is in my top recommendations, but San Felipe was the first castle built and it has a ton of important history, amazing views and great places to take pictures.

El Castillo San Felipe viewed from top, photo by @Wilson Ronda

Click Here for the Google Maps location of Castillo San Felipe del Morro

Click Here for more historical background about Castillo San Felipe del Morro

Operation Hours: 9:00 am - 6:00 pm

Price: Around $6 - $10

18. Last But Not Least: Get Lost in the Streets of Old San Juan 🕵️‍♂️:

This is something I always do when I am in a new city! I like to have the adventurous freedom; you never know what you would find. Try to at least to dedicate one to two hours to explore without a strict plan. I recommend it during the day though, better for pictures and would make you feel "safer". if you want you can also use this map below to guide yourself:

Location: GO WITH THE FLOW: ∞ !

Also, if you have extra time do these:

Visit the beautiful Raices Fountain and then walk through the Paseo la Princesa board walk until you reach el Morro. There is also a very nice outdoor restaurant there called la Princesa I highly recommend it.

Click Here for the Google Maps location

Click Here for more historical background

Visit Plaza las Armas and try to find the man and the pigeon statue. Take a selfie and tag me @backpackingluis in your stories if you can find it!

Click Here for the Google Maps location

Click Here for more historical background

Visit Plaza Colon and try to "conquer" him with a selfie. Don’t tag me in this one please.

Click Here for the Google Maps location

Click Here for more historical background

Visit la Catedral de San Juan Bautista. You can go inside to see the very well garnished church. Remember the crazy old guy? His remains are below the church, ask if you can find them and maybe you will find the secret for lasting for ever. Later, go sit down and relax in the park that is in front of the church, Plaza de la Catedral.

Click Here for the Google Maps location

Click Here for more Historical background

Click Here if you want to see more Old San Juan Museums. I recommend Galería Nacional if you are into art.

QUICK! Before continuing!

Check out my blog videos^ I made about my beautiful Puerto Rico! Where I show amazing beaches, waterfalls, food and music all by interviewing my tourist friends!

IV. My Top Restaurants In Old San Juan:

Note: Check restrictions due to COVID-19 and in Google for their operational hours.

a. My TOP Recommendations (Based on what I find the best local food):

Puerto Rican food, beer and view, at Garita de Yaz

$$$ Amazing food & fancy:

1. Marmalade

$$ Great food:

1. La Garita de Yaz

2. Punto Criollo

$ Greatest value for food food:

1. Café Manolin

2. La Mallorca

Click Here to open my top restaurant recommendation google list in Old San Juan

(Slide down when in list mode to see a map view like in the picture below)

b. My TOP restaurants in Old San Juan that have Vegetarian/Vegan options:

If you are Vegetarian, Vegan or want to try healthier food... I got you ;) :

$$ Amazing vegetarian food:

1. Verdemesa

2. Café Berlin

$ Greatest value for good food:

1. Deaverdura

2. Stuffed Avocado

Click Here to open my top Vegetarian/Vegan restaurants, more than 250, from around the island. Ask for vegetarian options. If you want you can also order a veggie mofongo or vegetarian sides on any restaurant in PR.

(Slide down when in list mode to see a map view like in the picture below)

c. My TOP Brunch restaurants in San Juan:

$$$ Great view and good quality:

1. Eter Rooftop

2. Casa Cortes (Old San Juan)

$$ Amazing Brunch:

1. La Carreta (Old San Juan)

2. Bistro Café

3. La Brasserie

4. MUSA

5. Latidos

$ Greatest value for Good Food :

1. La Mallorca (Old San Juan)

Click Here to open my top brunch restaurant recommendation google list in all San Juan

(Slide down when in list mode to see a map view like in the picture below)

V. Hang Out Like a Local In Old San Juan (Blogg Post Under Construction):

Old San Juan Night Life, photo by tripsavy

Click Here if you are into party and hanging out and want to check out my Night Life in Puerto Rico Guide. In here I give all my tips and locations of the best places to go out and have a great time.