The Beauty of Old San Juan [15 Photos]

The Colorful Building of Old San Juan Puerto Rico

San Juan, Puerto Rico is a diverse metropolis that caters to both travelers and vacationers alike.

If you’re looking for sun, sand and umbrella drinks, than the high-end resorts of Condado and Isla Verde are right up your ally. They’re clean, accommodating and everybody speaks English, so you can vacation just like you’re anywhere else in the United States.

For those of you looking for a bit more culture (and sexiness), I suggest you sneak off the resort and head down to Old San Juan, where the beautiful cobblestone streets and colorful buildings will make you feel more like you’re in Cartagena than Cancun.

You can explore the Spanish Castle of San Cristobal (T2T Quickie) and el Castillo San Felipe del Morro during the day and stroll through the peaceful narrow streets and waterfront walkways by night.

My only concern is that Old San Juan will loose some of its Spanish influence as the United States continue affirming their presence on the island, so I suggest you fly down and experience this beautiful colonial city for yourself, before it’s too late. 

With no passport required, Puerto Rico offers the most authentic Latin culture experience outside of Texas.

Don’t take my word for it that Old San Juan is a place worth visiting, check out these photos from my most recent visit and judge for yourself…

The Streets of Old San Juan, Puerto Rico

Plaza de Colon in Old San Juan Puerto Rico

Walkway along the walls of Old San Juan with a view of the Bacardi Factory in the distance

Street Art in Old San Juan Puerto Rico

The Capital Building in Old San Juan Puerto Rico

The Governor's Mansion in Old San Juan Puerto Rico

The Castle Walls of Old San Juan Puerto Rico

A Solider's quarters within the Castle of San Cristobal in Old San Juan Puerto Rico

Public gathering on the streets of Old San Juan Puerto Rico complete with giant speaker

Guarding the walls of Old San Juan Puerto Rico

Santa María Magdalena de Pazzis Cemetery in Old San Juan Puerto Rico

The Carmelo Anthony Basketball Court in Old San Juan Puerto Rico

Sunset in Old San Juan (no filter)

A young boy flys his kite in front of Castillo de San Felipe del Morro as the sun sets in Old San Juan

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My name is Gareth Leonard, a Marketing Director turned World Traveler with a passion for slow, meaningful travel. I have been traveling the world full-time for the past 9+ years and document it all on Instagram and YouTube. Come join me!


  1. Oh. My. Goodness. Your photos do an incredible job of showing off this great city! I’ve heard tons of great things about Puerto Rico but sadly I’ve never been able to make it down. This is a little renewed motivation to make it happen soon.

  2. Hi Gareth, we are new to your site and really enjoying reading about your travel adventures and look forward to following along in the future! I couldn’t agree with you more, Old San Juan is a treasure and one of our favorite travel destinations. The people are friendly, the history is rich and the colors are amazing not to mention the food! I can’t wait for our next trip back to Puerto Rico! Happy Travels!
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