Walking Around Old San Juan – A Self-Guided Tour
Walking Around Old San Juan - Why Visit Old San Juan, Puerto Rico
Before I get into my experience walking around Old San Juan, Puerto Rico, I would like to provide a brief history of this popular tourist area.
Old San Juan is the historical portion of San Juan, which originates as early as 1508. The city was originally walled in, but in 1897 the wall was demolished. This demolition led to a huge expansion of Old San Juan.
By 1940, many of the buildings were in bad shape and in need of repair. Over the years, the Government of Puerto Rico and many local banks have assisted in remodeling most of the buildings. Today, Old San Juan features beautiful colorful buildings, blue cobblestone streets, and many sculptures and fountains.
Be sure to look at a map prior to your walking tour of Old San Juan. Since the city was originally walled in, most of the roads are too narrow for two cars to pass through. Because of this, most of the streets are one-way, with some being pedestrian-only.
Author’s Note – During my visit to Puerto Rico, I had not yet decided to create this website. My trip was geared towards relaxing more than researching and learning about the history, culture, and geography of Puerto Rico. I hope to return to Puerto Rico in the future and update this page.
Walking Around Old San Juan - Table of Contents
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My Experience Walking Around Old San Juan
I began my self-guided walking tour of Old San Juan at the El Morro Fort. After an early morning visit to El Morro, I decided to head over to the San Cristobal Fort. Since the route took me directly through the heart of Old San Juan, it was the perfect opportunity to spend a few hours walking around the colorful streets.
Before beginning my walk around Old San Juan, I did spend a few minutes looking at a map. I wanted to make sure that I would visit some of the key tourist sights of Old San Juan during my walk.
As I entered the narrow streets of Old San Juan, I quickly disregarded the route I had mapped out. Walking around Old San Juan, I quickly was able to immerse myself in the narrow streets, Puerto Rican culture, and colorful buildings. Old San Juan is a truly historic Old Town that feels like going back in time.
During my time walking around Old San Juan, I didn’t make any purchases. What I did do was zig-zag the streets and take in the colorful scenery. Every block, it seemed that there was a beautiful sculpture, fountain, or building.
Even the fast-food restaurants had a historic look to them. While photographing the Subway, I was approached by a group of school children who were walking home from school. One of them asked me why I was taking a picture of the Subway. I explained that in Minnesota, our subways were not located in colorful buildings. The student laughed and walked around.
I am sure that I stood out as a tourist as I was the only one photographing the Subway and Burger King.
As I continued walking around Old San Juan, I eventually made my way out of the narrow streets onto what seemed to be the main road. This road led me to the San Cristobal Fort, where I would spend part of the afternoon looking at the historic fort.
Old San Juan Tours and Packages
I enjoyed walking around Old San Juan, on my own, without taking a tour. I didn’t feel a guide was necessary, as I wanted to experience the culture and look at the beautiful architecture.
If you would like to take a tour, I have linked eight tours below. Please note that as an affiliate of Viator, I will receive a small commission if you book using one of my links. This commission is at no additional cost to you.
 Old San Juan Walking Tour - $40.00 Discover the beauty of Old San Juan with writer David Rodríguez, author of The Rise and Fall of the Great Barbate. Tour Old San Juan's most important historic sites, learn about Puerto Rican culture, and experience the places and activities that authentically represent the stories and people of the past and present of Puerto Rico. |
 Fountain of Youth Tour of Old San Juan - $45.00 Discover the Beauty of Old San Juan with writer David Rodriguez, The Rise and Fall of the Great Barbate. From San Juan’s colonial Golden Age to the Gilded Age summer colony, discover the transformation of Ponce de Leon's city and people. Riots and rebellions, enemies and allies! Learn about Puerto Rico’s role in the revolution. See where scoundrels lived, pirates profited and criminals were punished. Find out why this colony was known as “Gold Island.” Explore the burial site of Ponce de Leon, Puerto Rico's founding father. Learn about the stone carvers, their art and the diverse people buried there who helped shape Ponce de Leon’s homeland. |
 Architectural Treasures of Old San Juan - $70.00 Enjoy the quaint cobblestoned streets of Old San Juan, while exploring the unique architecture that includes bastions, Fort San Felipe del Morro, the city walls, sentry boxes and the Cathedral of Saint John the Baptist which all served as the center stage of the most emblematic legends of the city as well as historical events. The walking tours is approximately 2.5 hours of walking will provide the experience of living and exploring a city that once was the most fortified city in the Americas. |
 Walking Tour of Old San Juan - $62.00 Do you want to explore and learn about Old San Juan, the historical city? With this 4-hour guided tour, you get what you are looking for. You will see lots of interesting historical places and buildings while your guide shares a unique and insightful perspective on the culture and history of Old San Juan. Guaranteed you will return home with lots of knowledge — a great add on to your Puerto Rican adventure! |
 Old San Juan Segway Tour - $103.69 Glide through Old San Juan’s 500 years of history on this 2-hour tour by Segway. Known as ‘The Walled City,’ Old San Juan was founded as a military stronghold and remains the oldest city under the American flag. On this small-group tour limited to 8 riders, zoom around effortlessly and see more than 25 attractions, learning from an informative guide about the city’s role during the Spanish empire, World War II and as a US territory. Capture stunning views of San Juan Bay, Castillo San Felipe Morro and San Cristobal Fort along the way. |
 Food Tasting and Old San Juan Tour - $105.00 On this tour you will learn how to cook and taste traditional Puerto Rican dishes by a local cook followed by a walking tour of Old San Juan for the perfect photo memories. RT transportation is provided from San Juan area. Cold drinks & tasting plate is included as well as privacy as our maximum capacity is 4 guest per tour. We give you the opportunity to get off of the beaten path for local cuisine, a beautiful beach view, as well as the history landmarks of Old San Juan. |
 Old San Juan Deluxe Walking Tour - $66.00 Visit one of the oldest cities in the world, San Juan, founded by the Spanish in 1521 AD. Get to know Old San Juan's history and sights on this walking tour of the city! With an expert local guide, you will discover the neighborhoods and learn about the powerful colonial influence. Starting from the Historical Hotel El Convento in Old San Juan, your local guide will take you on a 2.5 hour walking tour along the Paseo de la Princesa (Princess Promenade) to the La Fortaleza, which is currently the official residence of the Governor of Puerto Rico and the Castillo San Felipe del Morro. |
 Old San Juan Harbor Sail - $59.00 Set sail on a 19th-century style schooner for a journey through time, taking in more than 500 years of history. Uncover the beauty of Old San Juan, El Morro, La Fortaleza, and Paseo La Princesa from the water on this 1.5-hour tour, admiring important landmarks and stunning landscapes as you go. Keep an eye out for dolphins and beverages are included. |
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