Trade winds caress your face as you stand atop a 15th-century fortress in a UNESCO City staring out across the ocean lapping at the cliff edges as it has for centuries. Visitors pass by but you just reside in the stillness and friendship of the Iguana basking in the sun at your side. You get hungry and decide to head into the Old San Juan center to a restaurant along Fortaleza street. A wild-haired woman ushers you in, as she shoos two pigeon residents out of her restaurant that has been run by her family for years. You sit down and she hands you a local Medalla beer, you sip it, and realize that all your cares about life at home were washed down with that first sip of your cold beverage.

This is what I experienced anyway when I visited Old San Juan in May of 2022. I was there for a travel conference and was so enamored by the sites of Old San Juan and history here, I ended up ditching the conference to really DO what we were there to learn about – exploring and reporting better on cities from around the world.

There is a big difference between San Juan and Old San Juan, you see the difference in centuries collide within a matter of 1-2 minute drive through the city. You see the Spanish influence in the Castillos and fortresses, feel the religious devotion to the grandeur of the Chapel of St John, and learn about the miracle that influenced the Chapel of Christ. Walking along the blue cobblestone streets of San Juan is sure to delight every visitor, but there are a few suggestions and tips to visit that I will explain more in my article (link below) and in my video.

For a written detailed guide with an interactive google map, check out my article here: https://culturetrekking.com/tour-old-san-juan

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Chapters
00:00 Intro & Brief History of San Juan
01:36 Castillo San Cristobal
02:43 15th Century Air Conditioner
04:11 Uber in Old San Juan
04:19 Fortaleza Street in Old San Juan
05:01 Renting a car in Old San Juan
05:23 Grabbing a Decorated Popsicle to Cool Down
06:31 Harassment in Old San Juan (funny)
06:54 Fortaleza Fortress (BEST Instagram spot in Old San Juan)
07:12 Impromptu Dance Party
07:26 Why are Fortaleza Steet Stones BLUE?
07:31 Pigeon Plaza
09:36 Iconic Colored Doors of Puerto Rico
09:53 Cathedral San Juan Bautista
10:36 The Birthplace of Pina Colada
11:21 Food in Puerto Rico
12:11 WARNING!
12:38 Jardin de la Princesa
13:20 Paseo de la Princesa
13:59 Castillo del Morro (attempt #1)
15:32 Street Performers in Old San Juan (El Convento)
16:17 Seeing Wildlife in Old San Juan
16:26 Castle del Morro (attempt #2)
18:58 Plaza Colon
19:12 Colorful streets of Old San Juan
19:21 Street Art in Old San Juan
19:45 Visting La Perla Community
21:31 Plaza del Mercado (Nightlife in Puerto Rico)

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