Old San Juan: My Top Five

Old San Juan is one of my very favorite places.  Okay, full disclosure: My husband would tell you that I call most places we visit my “favorites,” but this one is legit–I promise!  We spent half of our honeymoon in San Juan and haven’t been able to stay away since.  In fact, we strategically book all of our cruises to leave out of San Juan just so we can have an excuse to spend a few days there before and/or after the cruise.  We have been a total of 6 times and are heading back in late June of this year.  140 days until San Juan ~ YAY!

Since I’ve got nothing better to do (you know, other than taking care of my kids, going to work, and sleeping at night, hehe!), I thought I would share a little San Juan love here on the blog.  Maybe it will help me get through these 4.5 months without twitching too much.  And maybe it will help you readers get a little bit of San Juan love for yourselves! ❤


My Old San Juan Top 5:

There are so many things that I love about Old San Juan.  I could probably name about 100 different foods, restaurants, experiences, landmarks, etc.  But for the sake of time, I thought it might be best to lump everything into a few categories and give the abridged version.  And just for kicks, how about I rank them on a scale of awesome to extra ridiculously awesome?  Or maybe just a regular old TOP 5 list will suffice!  😉  Alright, here we go…

#5 Shopping in Old San Juan

One of the great things in Old San Juan is the shopping.  It’s kind of strange that I say this because I don’t typically do much shopping in OSJ, but I still love to duck into the shops and browse.  If you spend enough time wandering the streets, you will find something for everyone: handmade crafts, decorations, wind chimes, art, jewelry, touristy clothes, and even high end shops like Coach.  You can even find stores like Walgreens and Marshalls if you need to do some practical shopping.  Personally, my favorite store is the Hecho A Mano (Made by Hand) store.  This little shop has unique clothes, jewelry, and other odds and ends, and I almost always find something worthwhile!

#4 Awesome outdoor plazas

I love that Old San Juan is filled with little plazas and parks.  We’ve enjoyed some great people watching and coffee-drinking from some of these.  We’ve also done a little shopping with the street vendors and even stumbled upon a concert one night.  One of the first plazas that we always start at is the Plaza de Colón, which is not far from the bus drop off and is a great beginning point for walking around the old city.  Plaza de Colón also has a great view of the San Cristobal fort.  Another favorite is right at the end of Calle del Cristo, where there is the Capilla de Cristo and then the Parque de Palomas.  This is an ideal spot to see a little bit of history and a whole lot of pigeons before heading down the Paseo de la Princesa!  There are plenty more worth visiting, but listing them all would defeat my purpose of keeping this list somewhat short and sweet (plus I cannot remember all of the names!).  I think you will just have to head to OSJ and find them all for yourself!  😉


#3 Stepping back in history

Another amazing thing about Old San Juan is its rich history.  The island was discovered by Columbus in 1493 and San Juan was settled by the Spanish in 1521.  This old city was fortified by city walls and two forts, the Castillo San Felipe El Morro and Castillo San Cristobal.  On our first visit there, we spent so much time in both the El Morro and San Cristobal forts and I just could not get over the idea that we were walking around in the very fortresses that had protected this beautiful port city!  Even after visiting so often, the fascination remains.  In fact, we are bringing some newbies along on our next trip and I cannot wait to take them straight to the forts!

#2 The Food

Coming in at a solid #2 is the food in Old San Juan.  The local cuisine is called “cocina criolla” and reflects the meshing of the Spanish and Caribbean cultures.  If you are looking for something else, the options are seemingly limitless with restaurants from many cultures–Spanish, Latin, French, Italian–take your pick!  There is also a restaurant group called OOF that boasts a small collection of trendy restaurants.  Now, I am not usually one to pick a restaurant based on its coolness factor, but having eaten at most of the restaurants in this group, I can say their food is actually good (especially the Latin-fusion cuisine at Parrot Club)!  I am hesitant to recommend a restaurant that I haven’t been to in years, but it would feel wrong to talk about the food in San Juan without shouting, “Go to Parrot Club!!!” from the rooftops (or rather from my computer keyboard).  There is one other restaurant that has held a special place in our hearts, and that is La Bombonera.  We found this place because it had been featured on Food Network and was supposed to the THE place to get breakfast.  Here is where, way back in 2006, we drank our very first cafe con leche and began our obsession with mallorcas. We ate there a few times that first trip and then made sure to eat there during each subsequent trip.  Until.  They.  Closed. Nooooooooo!  After 110 years of serving delicious food, they shut their doors.  But don’t worry, there is good news: THEY REOPENED!  And you bet I’ll be first in line when we get to San Juan!

#1 (drumroll, please) The charm of the brightly colored Spanish Colonial architecture and cobblestone streets

My absolute favorite thing about Old San Juan has got to be just walking up and down the streets and taking in all of the color and history.  Everywhere you look you see the brightly painted buildings, many with wrought iron balconies and clean white trim.  Then, when you can finally take your eyes off of the rainbow of buildings, you look down and notice that you are walking on cobblestone.  And I mean, who doesn’t love cobblestone streets, right??  Well, other than ladies in high heels–I imagine there’s got to be less love when each step is just one more chance to get stuck! 😉 But this is even better than your typical, run of the mill cobblestone.  The streets of Old San Juan were cobbled with bricks of iron slag that were used as ballasts in ships.  If I recall correctly, when the ballasts were no longer needed in the ships, they were dumped and then put to good use in paving the roads.  And they’re blue!   Cool, right??  Looking at these pictures from Old San Juan, you can see that a simple stroll down the street is like a feast for the eyes!

Are you online buying tickets yet?

Now that you have seen some pictures and heard my top 5, I am sure you are already on your favorite booking website looking for flights to San Juan, right???  Okay, probably not, but that’s okay!  As long as you were able to get a little bit of love for Old San Juan and a little travel fix (which I know I did), then I accomplished my goal!

Next Up:

More of beautiful Puerto Rico!


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