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In Pictures: Walking down Old San Juan’s colorful streets
By Tom Adkinson
September 15, 2023

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SAN JUAN, Puerto Rico – San Juan has been growing and changing for more than 500 years and today has its share of fancy buildings and gleaming towers, but they aren’t the attractions you come to see. Your real destination is Old San Juan, a place to stroll through history, delight in pastel-colored buildings, ponder why the cobblestones are blue, view the largest European fortresses built in the New World and, yes, be tempted by a rum drink or two. It is amazing to walk along streets platted in the 1500s and walk by buildings erected then. Old San Juan is manageably compact, and there always is another historic church, museum, restaurant or bar to entice you inside and away from the tropical heat. First-time visitors can especially benefit from guided walking tours such as ones from a company called Spoon, which deftly combines history with a half-dozen stops for local food or beverages.

‘Meet me at the plaza’

old san juan plazas
Most of Old San Juan’s streets are narrow, but plazas, fountains and church entrances provide open vistas. Image by Tom Adkinson

Looking down on the pedestrians

old san juan magenta building
The magenta exterior of a building in Old San Juan creates a bold frame for a resident to watch the parade of people passing by. Image by Tom Adkinson

Cobblestones with a story

old san juan cobblestone street
You will notice many streets in Old San Juan are paved in blue cobblestones (“adoquines” in Spanish). They were cast from furnace slag that the Spanish used as ballast in ships headed to the New World. Gold and other treasures provided weight for the trips back to Spain. Image by Tom Adkinson

What’s behind the green door?

old san juan restaurant mofongo pastales
The distinctive green exterior of this building tells you that you’ve arrived at the Restaurante El Jibarito, popular with locals for traditional Puerto Rican dishes such as mofongo (fried plantains usually stuffed with chicken or shrimp), empanadillas (tiny meat pies) and pastales (which you might think are tamales, but aren’t). Image by Tom Adkinson

All along the watchtower

sentry box san juan puerto rico
Sentry boxes (“garitas” in Spanish) provided views from San Juan’s fortresses, built and expanded over a period of 250 years. Spain brought enslaved Africans to build the structures. Image by Tom Adkinson

Libations ahead

san juan rum
You are never far from an invitation to slake your thirst while strolling through Old San Juan. Image by Tom Adkinson

Another red, white and blue

san juan flag
You will see this red, white and blue flag throughout Old San Juan. It is the flag of Puerto Rico, a commonwealth of the United States. Puerto Ricans are citizens of the U.S., but without all of its benefits. Image by Tom Adkinson


Trip-planning resources: and

(Travel writer Tom Adkinson’s book, 100 Things To Do in Nashville Before You Die, is available on

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