Old World Charm in San Juan, Puerto Rico! Part 1

Updated: Feb 28

Our itinerary:

  • Check in at The Gallery Inn

  • Exploring the streets of Old San Juan

  • Castillo San Felipe del Morro Fort

  • Dinner at SanSe Bar de Tapas

  • Dessert at Cortes Chocobar

As we flew in to San Juan's airport, almost 6 months after the devastation of Hurricane Maria and Irma, we were amazed at the blue tarps still visible on many of the rooftops.  No one missed the coverage of these two hurricanes, back to back against Puerto Rico and other Eastern Caribbean Islands, and it was evident that the island had been as ravaged as the reporting had said. 

Blue tarps on roofs, Landing in San Juan, Puerto Rico

With this as the first impression of San Juan, we were anxious what the conditions would be on the ground. As we cruised to our hotel, we were relieved to find the city and Old San Juan returning to its vibrant, yet relaxed vibe. The palm trees were still wind whipped and battered but the people of San Juan were snapping back into purpose and routine.



After the hurricane's hit, we contemplated canceling, or at least postponing, our trip but heard that the tourism economy could used the boost.  It was a good decision, one that became even more apparent as we spent time on the island. We made a point to purchase food items and souvenirs from local sellers and they were so appreciative of the chance to sell their goods again to eager tourists!


Rayna with a sculpted bird, hand crafted by a local artisan.

San Juan is a unique city, with one side boasting old world charm, and the other a hip, chic scene, yet juxtaposing both with equal allure.  The beaches and all inclusive resorts dominate the northern coast of San Juan and are some of the most beautiful beaches in the Caribbean. However, intrigued by history and art, our family spent most of our time in Old San Juan.  Our lodging was an experience of it's own at The Gallery Inn... so enthralling and unique that it gets its own post- Read it HERE! Art meets music in this unforgettable boutique hotel that is a functional gallery and recital location for the local Steinway piano club; yet it was also completely welcoming to Rayna with the free-roaming parrots and art scavenger hunt.


Our first stop (of the 2.5 days that we had in Old San Juan), was to begin at the place that had seen over 500 years of history and had easily survived the hurricanes: Castillo San Felipe del Morro. A 16th century citadel perched on the rocky tip of the island, this is the larger, more impressive fort of Old San Juan. Used in various ways throughout the years, from defending against pirate attacks to serving as an artillery site in World War II, this is a must-see on any trip to Old San Juan. History buffs will enjoy the massive list of military occupations and uses and anyone else will simply enjoy the impressive Spanish influenced structure and spectacular views from the top! Kids will love all the fun tunnels and posing in the sentry boxes!


As we left the fort, meandering down the cobblestone streets, the old world charm continued to unfold. The architecture of the buildings with the iron wrought balconies and lively pastels makes for a memorable combination. I captured a beautiful moment father and daughter, hand in hand, and it was added to my favorite photo collection! And Rayna, a self-proclaimed crazy cat lady, befriended some alley cats.


Our wandering soon brought us to an open plaza and we were treated with complimentary drinks (water & soda), appetizers and live music and dancing! The citizens of Old San Juan wanted to welcome and treat visitors and it was a nice gesture on a warm afternoon! Rayna was enthralled with the beautiful young lady's dancing and I was so excited for her to experience this element of Puerto Rican culture.



We spent the evening enjoying the culinary delights of Old San Juan! Upon recommendation, we dined at SanSe Marisqueria Bar de Tapas. My pictures of the interior were dark but it boasted a cozy bar up front and back room with arched doorways, which Rayna thought was neat. This was a wonderful place to try tapas and lots of flavors (and they offered a kid friendly menu). The croquettes of the day were delicious as well as the fried calamari and manchego cheese. Dessert was found at Chocobar Cortes- a hip little place to grab some of the best chocolate you've ever eaten! We indulged in a box to go of the Forteza choclate truffles.


The walk back to the Gallery Inn was so pleasant with warm breezes and abundant live music. After hours of walking up and down the hilly streets, we were eager to head to bed and rest up for another day!


Make sure to check out Old San Juan Part II for more sites that we saw!

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