The Enchanting Capital of the Isla del Encanto – Old San Juan

Writing about Puerto Rico will not be easy for me as writing about other places.  I lived in Puerto Rico since I was 2 years old until I finished high school so my experience of Puerto Rico is not just a trip or an extended visit.  However, I will try to highlight, through a few of these entries, what one who visits Puerto Rico can expect to see and experience.

There are many places in Puerto Rico worth seeing.  However, for me, Old San Juan is tops.  Consider that Old San Juan is a decade or so short of having been in existence 500 years.  Santo Domingo is older but, for the Americas, 500 is impressive enough.

The best way to appreciate the uniqueness of Old San Juan, which refers to the area formerly surrounded by a wall and the immediate vicinity, is by coming into the bay in a cruise ship (or maybe some other boat).  The tip of the island where Old San Juan is houses the El Morro fort, a very impressive fortification built centuries ago to protect San Juan de Puerto Rico from pirates from other European countries (even the mighty Francis Drake tried -and failed- to take San Juan).

El Morro fort in Old San Juan, Puerto Rico

The fort of El Morro and its beautiful and rolling grounds

From the fort, a huge wall surrounded Old San Juan with several gates (only one survives) controlling access.  A good bit of the wall remains, especially from the fort of San Cristobal towards El Morro, then to La Fortaleza (the governor’s mansion) to the Capilla del Cristo.  Seeing the old city surrounded by this wall, especially at sunset or nighttime is a sight to behold.

La Fortaleza (the governor's house) in San Juan, Puerto Rico

La Fortaleza (the governor’s house)

The fort of El Morro is a must see for anyone visiting PR.  Get a guide so you can understand how the fort operated, how it was used to defend the city, etc.  Step into a “garita” and feel what a Spanish soldier must have felt centuries ago serving as a sentry keeping an eye out for ships.  The fort is huge (take a water bottle if it is hot!).

Garita or guard house in Old San Juan's city walls in Puerto Rico

The quintessential image of Old San Juan: a garita along the city’s old walls and the lively ocean behind it

As kids we loved going to the fort.  The fort of San Cristobal is smaller but still an impressive site.   There is a cemetery below the ground of the fort of El Morro.  Local luminaries are buried there; however, be warned, getting to it is risky so I would actually recommend not going but, instead, cross the El Morro grounds and look down on the cemetery from the gaps in the wall.

The area around Plaza de Armas is the center of the town, where city hall is.  It is your typical Spanish plaza.  Nearby, you also have the Plaza Colon.  Anyone around will happily direct you to these places.  The Capilla del Cristo and the next door Parque de las Palomas are local favorites.  The Capilla (chapel) was built on the edge of a cliff in honor of a jockey not dying (a very long time ago) when he and his horse went off the cliff on a downhill race down the Calle del Cristo.  People leave items as thanksgiving for prayers answered.  It is a charming site.

Beautiful simple balcony in Old San Juan, Puerto Rico

Beautiful simple balcony in Old San Juan

Old San Juan is a great place to explore on foot as it is very compact.  Walk to the Cathedral, enter the hotel across the street (“El Convento“, a former convent), walk down by the waterfront, explore the backstreets and examine the architecture.  If you get lucky, take a peek inside any of the houses (people do live there!); worst case, at least go into shops or eateries that retain the inner courtyard so you can appreciate how people lived and still live in these magnificent buildings.  The cobblestone streets and the architecture really take you to a different time (if you can ignore the cars!).

Old San Juan street in Puerto Rico

A side street near the Cathedral

As you approach the cruise ship area, the number of souvenir shops increase exponentially but in the rest of Old San Juan, you will find shops where the locals also shop and souvenir shops that are more reasonable.  I remember as a child my mother going to Old San Juan on a Saturday to go shopping.  There are many places to eat and many of those being oriented to tourists but, for a local style lunch, el Siglo XX is a classic (Calle O ‘Donnell).  Other well known eatiers are La Bombonera and La Mallorca (some of these may be closed by now…).   If the day is hot, stop at a piragüero, and get the piragua (shaved ice with a syrup with the flavor of your choosing).

Nightlife in Old San Juan is abundant.  The bars in the Calle del Cristo were famous in my time in PR and are likely still popular with the local crowd.  I believe that Calle San Sebastian has also developed as an area to go out at night.  The area by the cruise ships also has places to eat and drink but, to me, having known another side of Old San Juan, that would feel too touristy and I would avoid it.  (Anyone with more current info and perspective, please comment if all this is outdated info!!  I don’t claim to be current on where to go for nightlife, but I know there is!)

If you have kids, the forts and adjoining grounds will clearly be fun for them – but get a kite and be ready to fly it!

Kites in the blue sky in Old San Juan, Puerto Rico

Kites in the blue sky on the ground of El Morro – taking me back to my childhood

Check out this link for more info on what to do with kids:

It is hard to do Old San Juan justice in any write-up.  It is a charming, deeply historical, and beautiful location to see and explore!



  1. Great write up of Old San Juan. I’d just add that if you wanted to see the cemetery close to El Morro fort, provided you go during the day, you should be fine. There is an access road now off the main road that takes you to the entrance.

    South Fortaleza street seems to be one of the happening spots in Old San Juan for restaurants.

    I would also recommend a stroll along the Paseo La Princesa, whcih takes you along the bay towards the San Juan Gate.

    • Thanks for the info, more up-to-date than mine. Was not aware of the access road you mention. I recall as I child, when one could drive down through the San Juan Gate, that I loved when my Dad drove me through it – it seemed the car was going to go straight into the water, quite the thrill ride!

  2. Great write up on Old San Juan. I wish I got a guide when I walked around El Morro because I would’ve got so much more out of it.

  3. I like your personal perspective on Old San Juan and how it used to be while you lived there. Thanks for including info on what to do there with kids! I agree that most children love forts; I had the same thought when traveling through Italy with my daughter. I thought, How cool it must be to live here…
    Francesca recently posted..White Pines Forest State Park (Illinois): A photo essayMy Profile

  4. Puerto Rico is a place that got on my radar recently – I am sure it will be a pain to get to, but now you really made me want to go. Had no idea you had a couple Puerto Rican bones in your body 😉
    @mrsoaroundworld recently posted..Cooling down in sunny Scottsdale, ArizonaMy Profile

  5. Lovely looking place. Made me want to go and kick back in the city with you and Mrs O.
    Will – GrooveTraveler recently posted..Kick-Ass Spanish Festivals: Figueres AcusticaMy Profile

  6. BEAUTIFUL! I must go here and I must have you take me. I’d love for you to show me Old San Juan and your Puerto Rico. {Then we’ll take off for Patagonia.}
    Leah Travels recently posted..A Click & Comment to Help Cure Ovarian CancerMy Profile

  7. When I FINALLY make it to PR and San Juan, I will be sure to talk to you, Raul. Cruise ship, huh? Oh… kay… I’ll trust you. 🙂
    Pola (@jettingaround) recently posted..Book pick: ‘Paris: Wish you were here!’My Profile

  8. Great to have insight from someone who once was a local and has since traveled the world.
    Traveling Ted recently posted..Travel Photo Roulette contest WTF moment in VietnamMy Profile

  9. Puerto Rico is at the very top of my Caribbean list and Old San Juan is one of the primary reasons. Wonderful write up Raul, and thanks for sharing.
    John recently posted..Six Pics: On The Tourist Trail In MykonosMy Profile

    • OSJ is a jewel of architecture and history. The metropolitan area, not so much. Other wonderful things in the island are the beaches (of course), the tropical forest (El Yunque), and the bio-luminescent bay (La Parguera). Hope you get to check it all out some day, John.


  1. […] to see small changes, such as in the Casco Viejo, the old part of town that reminds me so much of Old San Juan except the latter has been renovated extensively and kept up quite nicely.  This time, I could […]

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