Two days in historical Old San Juan, Puerto Rico

After the deep freeze in Canada, the warm tropical weather of Puerto Rico was welcome at first. But we wilted fast in the heat, so if we missed some important sights, it’s because we were recovering under air conditioning.

Before the United States took over in the late of 19th century, San Juan in Puerto Rico was an important Spanish gateway to the Caribbean islands since the 16th century. Fortresses and city walls were made to fortify this island to protect their harbors from the invaders. Behind the mighty stone walls, the old city of San Juan developed.

Now inside a fully air conditioned room, we want to share with you the highlights of our short visit to Old San Juan of Puerto Rico!

1. Castillo San Cristobal

Castillo San Cristobal in Old San Juan, Puerto Rico

There are 3 fortresses guarding Old San Juan, 2 of them on San Juan island, and Castillo San Cristobal that is said to be one of the largest Spanish fortresses in the new world, is one of them. The fortress itself is architecturally beautiful and the coastal view is fantastic. You can also see a dark room in the dungeon where the prisoners were kept in the past, where the wall is covered by galleon sketches by the prisoners that yearned for the outside world.

2. Castillo San Felipe del Morro (El Morro)

El Morro in Old San Juan, Puerto Rico

Located in the end of the island, this fortress together with another one in a tiny piece of land across the strait, bombarded any unwanted ships that were daring enough to approach San Juan Harbour. Just like Castillo San Cristobal, this rather symmetrical and triangular fortress is also beautiful. My favourite part is a straight ramp through a long tunnel with staircases on both sides. I wonder whether they used this ramp to move around heavy cannons in the past.

3. City wall

City wall and sentry box in Old San Juan, Puerto Rico

These city walls served as protection for San Juan in the past. Even though some stretches of the walls have been removed to allow the city to grow, you still can see most of it surrounding Old San Juan, from the Castillo San Cristobal to El Morro, down to the San Juan Gate. This several-foot-thick wall is massive and imposing. It’s fun to walk through the gaps in the wall, just don’t fall over the edge, since it’s not gated (leash your kids). Check out the sentry boxes along the wall, even though they mostly smell like urine.

4. Coastal view

The coastal view from Castillo San Cristobal in Old San Juan, Puerto Rico

From the height of the city walls and the fortresses, we enjoyed the gorgeous views to the deep blue Atlantic ocean, the shore line, and Old San Juan City with its pretty pastel colored houses.

5. The view of the dangerous La Perla slum

La Perla in Old San Juan, Puerto Rico

La Perla is a neighbourhood outside the city wall between the 2 fortresses facing the ocean. Ryan mentioned it was the dangerous part of the city, and tourists are strongly recommended not to go there. This slum neighbourhood, still somewhat in pastel nuance but here and there decaying, is such a contrast with the nice buildings in the rest of Old San Juan. Attracted to this decayed pastely neighbourhood, I just took some quick photographs from the gaps in the city wall. Two guys down there waved to me, signaling me to come down. I just waved my hand back, and left. It looked quite normal and peaceful to me. Later on we asked about it to some locals. They said the part is indeed not recommended for tourists to go, since it’s a drug dealing neighbourhood. They might sell you drugs if you are lucky, or you might get shot if you are not.

6. Santa Mari­a Magdalena de Pazzis Cemetery

Santa Maria Magdalena de Pazzis Cemetery in Old San Juan, Puerto Rico

Santa Maria Magdalena de Pazzis Cemetery in Old San Juan, Puerto Rico

Lying outside the north city wall adjacent to the El Morro is the Cemetery of Santa Maria Magdalena de Pazzis. This white cemetery looks gorgeous, walled by the city wall in one side and the blue Atlantic Ocean on the other. In the middle of the cemetery sits a charming pink domed rotunda.

7. Iguanas

Iguana in Castillo San Cristobal, Old San Juan, Puerto Rico

In the yards of the both fortresses, there are a lot of iguanas sun basking. They are big, green, and spiky on the spine. When they raised their heads, we could see that fan shaped neck skin hanging between the head and the body.

8. Walking around Old San Juan

Colorful houses and dark blue cobblestone in Old San Juan, Puerto Rico

Old San Juan is not great only for the fortresses and the city walls, but also the charming historic colonial neighbourhood. Nowadays there are still people living and working in this area, although it’s extremely touristy with a lot of restaurants and stores. Even though it’s more touristy than we’d like, they have preserved this historic town well, so it still has its pretty and old appearance from colonial times.

9. Houses and buildings in various pastel colors

Casa Rosa in Old San Juan, Puerto Rico

These pastel colored buildings are very charming, they also come with antique looking doors and windows. So many different color they have, all in pastel tune: blue, pink, red, orange, green, brown, yellow, purple, and it seems they are in agreement with their neighbours that no two buildings stading side by side could have the same color.

10. Dark blue cobblestone road

Cobblestone road is charming enough, but here, it’s in dark blue hue too! (See picture #8)

11. Pigeon’s Park

Pigeon wall in Old San Juan, Puerto Rico

Pigeon’s Park? This so called Pigeon’s Park in the map, near the Cristo Chapel, named appropriately to the fact that there are so many pigeon in that small park. These pigeons didn’t care when we walked through them, so we had to be careful not to step on one. The park is walled in one side, and the wall has a lot of square holes. And guess what, each holes are jam pack with pigeons! We escaped from this park before any droppings fell on us. We even saw a small girl who had actually picked up one of the pigeons and was holding it in her arms!

12. San Juan Cathedral

Carlos Manuel Rodriguez altar in the Cathedral of Old San Juan, Puerto Rico

This white washed church looked so in tune with the rest of the old town. The main altar and ceiling were really nice, but there’s one of painting on the small chapel that puzzled us: a man in a grey suit! I mean, usually we see the paintings of holy figures in ancient outfits and backgrounds, not a modern man dressed for a day at the office. Apparently he is the “blessed” Carlos Manuel Rodri­guez, a Puerto Rican that was beatified by Roman Catholic Church in 2001 and a candidate for sainthood.

13. Totem Telurico

Totem Telurico in Old San Juan, Puerto Rico

Totem Telurico is a contemporary sculpture in the Plaza del Quibto Centenario, built in 1992 for commemorating of the 5th centenary of the discovery of America. This totem has a little bit unusual appearance, it’s brown like clay and rather featureless. That’s the only thing I can say about it, but in its modesty, it looked gorgeous against the blue sky.

14. Piña colada

Pina Colada at Barrachina, Old San Juan, Puerto Rico

Drinking the piña colada in its birth place, couldn’t get more authentic than that! This blend of rum, cream of coconut, pineapple juice and ice is so refreshing after a long walk in this hot city. We are aware that there are several different version of how or where piña colada was first invented, but for us, it’s the Barrachina restaurant!

15. Puerto Rican food

Mofongo and pork chop in Old San Juan, Puerto Rico
Mofongo and pork chop


We tried mofongo, the Puerto Rican fried plaintain based dish, as well as Puerto Rican tamale. We thought those were okay, not going too wild about it. We certainly enjoyed the fried plantains that you can order as a side dish.

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28 Responses to “Two days in historical Old San Juan, Puerto Rico”

  1. Dalene - Hecktic Travels
    8 March 2011 at 9:31 am #

    But it’s good luck to have birds poop on you!! (So my Mexican friends tell me…)

    Nice round-up of San Juan! And when you get to see us in Honduras, we can even take you to EAT iguana, if you like… =)
    Dalene – Hecktic Travels´s last post…A Lesson From My Mom

    • Dina
      8 March 2011 at 10:37 am #

      About the bird poop: Yuck, is that so? Okay, maybe next time I should wish for the droppings!
      About Honduras: Excited to see you guys in Roatan! Today we will fly from Puerto Rico to Honduras, I’ll let you know asap when we make decision about Roatan. Iguana can be eaten? I can’t imagine how it tastes like! Do you guys like it?

  2. Andrea
    8 March 2011 at 1:06 pm #

    Gorgeous photos! So glad to see you both on the road again and out of the cold! We´re just south of Santiago and heading towards Patagonia. Let us know when you get closer to us (I sense it will be awhile)

    • Dina
      8 March 2011 at 3:38 pm #

      Thanks! And we are so glad to be on the road again, as well as excaping the Canadian winter. And wow!! You guys are in South America already? When did you guys make the leap? Let’s keep each other posted, it will be cool if we can meet up again!

      • Alex
        17 December 2013 at 9:32 pm #

        Puerto Rico is not in south America, it’s in North America.

        • Ryan
          29 December 2013 at 3:40 pm #

          It sure is. Dina was talking to Andrea who (was) in Patagonia – South America. Thanks for your comment, though!

  3. sabina
    8 March 2011 at 6:46 pm #

    A new post! ;) You took some incredible photos! I love that totem pole. And I love forts, so Puerto Rico might interest me more than I had thought. I know what you mean about the heat. I haven’t felt cold weather in six months, until yesterday. I actually had to wear a jacket and long pants here in Hue, Vietnam. I was surprised that I had SO much more energy than usual. Living in freezing cold Connecticut, I am not used to hot weather at all, so six months of it has apparently taken a toll on me. I felt like a new person yesterday. Tonight I head 12 hours north to Hanoi, where it will be even colder, so perhaps tomorrow I’ll feel like a newborn baby ;)

    • Dina
      9 March 2011 at 4:23 am #

      Hahhaha, while you will turn into a newborn baby, I gain much wrinkles out of staying under the strong sun without sun screen lotion (I just don’t like the sticky feeling of it).
      (Yes, a new post, I know, finally!)

  4. Angela
    9 March 2011 at 7:12 am #

    Very informative piece. Usually the history behind touristy places is neglected, while it’s always interesting to see beyond beaches and landscapes. Great shots :)
    Angela´s last post…Unearthing rural India with locals- one city at a time

  5. ansella
    9 March 2011 at 9:25 pm #

    And where is the picture of the cutest traveler that I know in Puerto Rico? ;p

    Have fun dear Dina!
    ansella´s last post…mark the X

    • Dina
      10 March 2011 at 2:35 am #

      *tersipu-sipu nih*

  6. Audrey
    10 March 2011 at 12:32 am #

    Beautiful photos, I was in San Juan 15 years ago, but only got a half day to spend. I would love to go back sometime. I remember stopping at one of the fortresses before embarking on a cruise. Some cranky guy on the bus yells out, “what to heck are we stopping here for?” LOL, some people are so funny.
    Audrey´s last post…Guanajuato- A Youthful And Lively City

    • Dina
      10 March 2011 at 2:37 am #

      Thank you :)
      Wow, I will feel like punching that guy, lol!!
      Which cruise ship were you in? Was it a Caribbean island cruise?

  7. Audrey
    10 March 2011 at 12:06 pm #

    Yes Dina, it was a Carnival cruise that went to 5 different islands, St.Thomas, Barbados, etc. We got it super cheap because it was the last cruise of the season (end of April) The ship was really old, it’s probably sunk by now, lol. We really enjoyed it though. The majority of the passengers were from San Juan. They were so much fun, breaking out their own instruments on deck at times and having sing-alongs and such.
    Audrey´s last post…Banff Springs Hotel- Alberta Canada

    • Dina
      25 March 2011 at 1:58 pm #

      Haha, good that it didn’t sunk with you in it :) Sounds like it’s a lot of fun with a lot of cultural exchange from the Puerto Ricans!

  8. Maria Pavel
    10 March 2011 at 11:49 pm #

    I always love your pictures, Dina.
    Most of the times i don’t even get to reading the text, the pic is enough to convey the message (i know that’s not too nice of me).
    And that Puerto Rican food, mmmm… got me really hungry.
    Maria Pavel´s last post…Certified Nursing Assistant Practice Test

    • Dina
      25 March 2011 at 1:59 pm #

      Thanks :) I love it when the pictures can talk themselves!

  9. Tijmen
    11 March 2011 at 9:01 am #

    Looks like a great place to visit, always love the cities where they have these old historical buildings. The Tótem Telúrico does look a bit strange though :)
    Tijmen´s last post…Customs and Traditions in India

    • Dina
      25 March 2011 at 2:00 pm #

      The totem does look a little bit out of place, in an old historical city like that.

  10. Suzy
    13 March 2011 at 4:07 am #

    I’m dying to go to Puerto Rico. Looks and sounds like a great place, minus Pigeon Park. You couldn’t get me to go in there for I hate those flying rats.
    Suzy´s last post…Blarney- Ireland Wishes You Were Here

    • Dina
      25 March 2011 at 2:02 pm #

      The pigeon park was a weird place, and it’s even weirder to see a little kid just picked one up from the ground and started to cradle it.

  11. Akila
    22 March 2011 at 4:20 pm #

    Dina – We loved the pastel houses, too! There’s so beautiful, aren’t they? And love me some fried plaintains!

    • Dina
      25 March 2011 at 2:03 pm #

      They are way cute, aren’t they! And those sweet fried plantains, I wish I have them now! I like it better than the plantain chips.

  12. Ruth
    24 March 2011 at 11:48 pm #

    Great representation ok Puerto Rico in here. I like it. Glad to see you guys had a good time at the island. By the way, I was pooped multiple times at the pigeon park. When I was a kid, the school planned a trip to Old San Juan every year. We always visited Pigeon Park. The worst was when they pooped your head, exactly the top of your head because you cannot see the mess and nobody wants to help you to clean yourself.

    • Dina
      25 March 2011 at 2:06 pm #

      Nice compliment from a Puerto Rican! Pooped multiple time? Gross, haha! Exactly on top of your head? Wow, they are great in targetting :D
      I was lucky I didn’t get pooped this time, considering I seem to attract animal poop around me.

  13. Haley
    7 June 2011 at 4:09 am #

    Such beautiful lanscapes.It seems that you had great time.Hope to follow every your travel
    Haley´s last post…When do the 2010 mongoose and gt bikes come out

  14. John@LI veterinary endoscopy
    31 May 2012 at 2:38 am #

    Wow, amazing. Puerto Rico is has a rich old culture. Looks like a lovely place to bond with my family. Thanks!

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