The Charm of Old San Juan

Last year we visited Old San Juan during a Caribbean cruise out of Miami. We fell in love. Colorful buildings, friendly people, easily walkable, good food, and great culture. What’s not to like?

In planning our annual winter escape for December 2018, we decided to do a cruise again. However, instead of leaving from the usual ports of Miami and Fort Lauderdale, we opted to leave from San Juan instead. This gave us a chance to explore Old San Juan some more instead of just a half-day port of call.

Up early, we flew out of our home airport of Milwaukee on Southwest Airlines, connected at Baltimore/Washington, and arrive at San Juan’s airport in the afternoon. After being whisked away by taxi we arrived at the Sheraton Old San Juan to check in. We like its central location. Everything in Old San Juan is no more than a 10-15 minute walk from the hotel.

When we had left Milwaukee in the morning, it was 22 Fahrenheit. Now it was 82! We put on some shorts and headed out on the streets of Old San Juan.


Old San Juan

I love the colors in Old San Juan. Everything is absolutely vibrant–a feast for the eyes! Speaking of feasting, we were hungry after a day of air travel. We wandered around and found ourselves in Plaza Colon. We found a restaurant – Cafe Berlin – and both of us had delicious plates of mofongo.

photo dec 07, 4 07 27 pm

Then we walked around after dusk enjoying Old San Juan all lit of for the holiday season.


Old San Juan

The following morning, we explored Old San Juan a bit more. Last year, we toured the El Morro fort. This time, it was off to its counterpart, Castillo San Cristobal. Finished in 1783, the expansive fort has good vistas of Old San Juan. Your ticket will also get you into the El Morro fort too. So if you have time, try to visit both.


Castillo San Cristobal


Castillo San Cristobal


Castillo San Cristobal


Castillo San Cristobal, looking towards La Perla and El Morro

After touring the fort, we meandered through the streets of Old San Juan taking in the sights.


Old San Juan


Cats of Old San Juan


Catedral Metropolitana Basílica de San Juan Bautista


Looking towards La Fortaleza

There was a colorful surprise on Calle Fortaleza leading to La Fortaleza, the official residence of the governor–umbrellas! This special art installation celebrates the people of Puerto Rico. It’s definitely worth a stop (while it’s there) for a great Instagram capture!

photo dec 08, 9 09 23 am

Calle Fortaleza umbrellas

photo dec 08, 10 10 36 am

Calle Fortaleza umbrellas

For a self-guided walking tour of Old San Juan, check out TripSaavy.

Here are some pics from Old San Juan. For more, check out my Flickr album.

One Comment on “The Charm of Old San Juan

  1. Pingback: Caribbean Cruise: Celebrity Summit Review | Travel on the Side

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