Cruising the Caribbean: 6 hours in Old San Juan, Puerto Rico

During a seven-day cruise through the Caribbean, I relaxed on beaches that looked exactly as they did in the pictures I once viewed on a laptop screen. Each port of call was another dreamy beach location. That was until our last port of call in Old San Juan, Puerto Rico.


Unlike the other ports I previously visited, Old San Juan was quaint and cultured. Even as one of the biggest ports of call for cruise liners, and with so many tourists passing through, the city has maintained its rich historical and cultural heritage.

While all three previous destinations greeted me with the most beautifully groomed beaches one could visit, it was Old San Juan’s historical architecture and landscape that completely drew me in. The commercialised experience that the other ports oozed was replaced by a city bustling with day-to-day life.

Entrance of Fort San Cristóbal

In the mere 6 hours I spent in Puerto Rico, I fell in love with Old San Juan.

Old San Juan was radiant with friendly locals and other tourists. The city was full of vibrant architecture and narrow streets lined with brightly coloured apartment buildings and storefronts, which evoked an excitement I hadn’t felt at the other locations.

Artwork painted on the side of a building
Artwork painted on the side of a building

As I wandered through the city, I saw Old San Juan celebrated in the artwork on the sides of buildings. Depictions of the city burst off walls in the brightly coloured paint just as you see them play out in real life. Portrayed on the walls were florists carrying large bouquets of flowers, narrow cobblestone streets lined with buildings painted in tropical hues, wrought iron wall lamps casting buttery light, and the age marks on the sides of buildings and sidewalk.

Fort San Cristóbal

Away from the colourful and cozy streets, I headed for the coastline to find one of Puerto Rico’s largest forts.

Overlooking the Atlantic Ocean, Old San Juan’s Fort San Cristóbal, officially known as Castillo San Cristóbal, was built in the late 1700’s to defend the city from any potential land-based attacks. Nowadays, the UNESCO World Heritage site is a popular destination for tourists to feast their minds on the city’s rich history, while taking in the elevated views of San Juan and the coast.

While Old San Juan was not groomed for tourists like previous destinations, its cultural and historical ties only added to my infatuation with the city. I never felt the same appreciation for the previous ports, and over time my memories of the three beach locations became muddled because they were all very similar.


Even though the beach ports were visually stunning, they lacked the aesthetic of a strong cultural and historical identity that thrives in Old San Juan. What makes Old San Juan such an alluring place to visit is the authenticity that comes from embracing the physical, social, and cultural aspects that make the city unique.

Looking across the Old San Juan shoreline from one of the lookouts at Castillo de San Cristóbal

Unlike Old San Juan, some ports of call are privately owned and operated by cruise lines, and, although beautiful, they resonate a sense of forged identity for commercial purposes. At these ports, I felt as though something was missing. Even though I knew I was in another country or on another island, my physical surroundings didn’t make it feel that way. At the beach ports, there was significantly less cultural, historical and social influence.

The beauty of Old San Juan was being greeted by Puerto Rican business owners as I wandered through the vibrant streets and asking locals for directions when I got lost.

Views from Fort San Cristóbal

Gaining my bearings, by asking locals where I was and how I could get to where I was going, was what made getting to know Old San Juan that much more of an adventure. For me, being able to leave with a sense of discovery after being so unfamiliar with a city is what makes travelling that much more intriguing.

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  1. I love the artwork on the side of that building. And San Juan looks gorgeous overall.

    1. It certainly is! I wish I could’ve spent more time in Old San Juan to explore more of its little roads and street art.

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