Old san juan walking tour: Old San Juan Walking Tour (Self Guided), San Juan, Puerto Rico

A Self-guided Walking Tour of Old San Juan

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When planning our cruise to the Eastern Caribbean, there were many excursions to choose from at each port of call. We had already planned kayaking, snorkeling, zip line adventures, and water parks at our other ports and we were looking for something different to do in Puerto Rico. John had visited many years ago and suggested that we take a self-guided walking tour of Old San Juan.


Old San Juan Shore Excursion

The ship docked at the San Juan cruise port terminal, and we were able to walk into the old town from there. Consider a self-guided walking tour of these sites for your shore excursion instead of the usual offerings – it is a lovely day of wandering.

Upon leaving the Carnival Breeze, the bright colors were the first thing to catch my attention. Even though there were grey clouds and misting rain during our visit, Old San Juan is colorful, vibrant and has a real charm about it.

Where to eat in Old San Juan

Since it was raining when we arrived, we decided to have lunch first before exploring Old San Juan on foot. You’ll want to see Plaza Colón, a beautiful square with markets and a statue, so I recommend Cafe Berlin. Overlooking the square, it has a great terrace for people-watching; and serves delicious Puerto Rican food. I had the Ceviche and it was a real flavor pop!

Things to See in Old San Juan

I recommend that upon arrival at the cruise port, you walk north towards Plaza Colón. This walking tour will take you in a counter-clockwise direction around Old San Juan.

Castillo San Cristóbal

Castillo San Cristobal is the largest fortification built by the Spanish in the New World. In 1783, when it was completed, it covered about 27 acres of land and basically wrapped around the city. After nearly 100 years of peace, one-third of the fort was demolished to help ease the flow of traffic in and out of the walled city.

The fort served many purposes during its time and in 1961 the US Army moved out of the fort. It then became the jurisdiction of the United States National Park Service, to be preserved as a museum only.  

There are 3 levels at the fort.

  • Level 1 is the main plaza and lowest level.
  • The 2nd level is the main firing battery.
  • Level 3 is the observation area and the highest level.

We explored them all, from the lowest of the dark tunnels to the highest hills above. Admission is free for children 15 and under and for adults it is $5.

Garita del Diablo

One of the sea wall fortifications of Castillo de San Cristóbal is Garita del Diablo. This bastion is right down by the ocean, and you have to walk through a graveyard to reach it. It is said to be haunted by spirits. Spanish soldiers used to be sent out on patrol here as punishment!

Old Fortifications

Upon exiting the fort, we chose to walk along part of the old wall that once protected the city. Payton enjoyed running around the open spaces along this coastal area. John and I spent a long time looking out over the Atlantic Ocean. You can see why the fortifications existed along this coast, Puerto Rico has so much coastline to invade!

There are several bastions along the north coast of Old San Juan. Bastión de Santo Tomás, Bastión de Ánimas, Bastión de San Antonio, and at the entrance to the San Juan Harbor, Castillo San Felipe del Morro.

San Felipe del Morro is a 1-mile walk from Castillo San Cristóbal, and the nearby Panoramic overlook has a good view back towards where you’ve just walked.

Old Town Shopping

Had enough of fortifications? Time to weave your way through the streets of the old town for some shopping!

Weave your way south down Calle del Cristo, and then east along the great shopping street of Calle de la Fortaleza.


If museums are more your thing instead of shopping, there are a few in the upper left quadrant of Old San Juan. Museo de las Américas – a museum of pre-Columbian and modern art from the Americas. Casa Blanca, a museum in a beautiful estate, built in the 1500s for the Spanish conquistador, Ponce de León.

Or learn more about the local people at the Institute of Puerto Rican Culture. Built in an old convent, it is definitely an interesting place to visit. Not far from there is the Museum of Art and History, which is housed in an old market building with an internal courtyard.

Needless to say, there is more in Old San Juan than can be seen or done in 1 day of shore excursion. So, pick what suits your tastes on this self-guided walking tour of Old San Juan.

Old San Juan Parks

The joy of a self-guided walking tour is that you can stop when you need to. In the summer, the many lovely gardens and coastal breezes will help you cool down. Payton loved Parque Las Palomas on the south coast of Old San Juan. It has beautiful scenic views, and A LOT of friendly pigeons. I don’t think we’ve ever seen so many. Relax and feed the birds at this park, but maybe don’t try and eat a sandwich – they might steal it!

Walk back towards the cruise port via Paseo de la Princesa, this manicured promenade has fountains, cafes and shady spots to get out of the sun.


Interesting Fact: If you have ever visited Savannah, Georgia, then you know about the cobblestones that make up River Street downtown. Here, in Old San Juan, they have cobblestone streets as well, but they are blue!

These bricks were cast out of the remains of the iron-refining process. The moisture of the iron gives them their deep blue color. Legend says that if you listen closely, you can hear the footsteps of the Spanish soldiers who once walked the streets.

See more of our Caribbean cruise adventures in Amber Cove, the US Virgin Islands, and Grand Turk!

A Self-guided Walking Tour of Old San Juan

We really enjoyed our day in Old San Juan, Puerto Rico while cruising with Carnival. I would recommend taking some time to explore all that is there. The colorful city, the historical forts, and the vast views of the Atlantic Ocean are all worth the visit. From the cruise port, everything we experienced was within a 20-30 minute walk from the port. Perfect for a self paced walking tour!

Have you visited San Juan? If so, what was your favorite spot?

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Old San Juan walking tour, Puerto Rico

Old San Juan walking tour, Puerto Rico

Schedule: 10AM — 12Noon

Meet: San Francisco Church Plaza

Rate: $50pp

Book Now

The rise of a colonial town inside the Fortress City of Puerto Rico

«The Story of Old San Juan» is a 2 hours walking tour about exploring and understanding the why, when, who and how the cobblestones, balconies, the colors, historical homes, unique burial site, the wall and military fortifications are still available to be appreciated by the World.

«The theme of this tour focus on the unique stories behind the construction and survival of a colonial town known as Old San Juan in Puerto Rico.»

Debbie Molina Ramos, Tour designer and Licensed Tour Guide since 1999

Story-telling tour guide

Debbie has been narrating history in Old San Juan, Puerto Rico since 1998.

Ponce de Leon Burial Site

Find out how Ponce de Leon shaped the colonial city.


The why, when, who, how, where of the cobblestone’s story.

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Explore historical sites and see how the preservation codes made possible for Old San Juan become the best preserved 16th Century Spanish Colonial city in The Americas.

Debbie Molina Ramos, Tour designer and Licensed Tour Guide since 1999


An Old San Juan walking tour that is educational; therefore, ideal for student groups.

Go underground

Burial sites have there unique stories.

Book Now

Rain or shine…

Availablilty: Check calendar
Schedule: 10AM to 12N
Meet: Plaza Salvador Brau next to San Francisco Church.

Salvador Brau Plaza
next to San Francisco Church
Tour begins at 10AM or 3PM.


  1. The currency use for our transactions is the United States dollar.
  2. Booking confirmation will be received at time of booking. Check your inbox and spam folders. We accept paper vocher or the e-mail using your smartphone.
  3. We refund when we cancel; however, do read the details for our no refund policy.
  4. Sites: Booking this tour is an acceptance and understanding that Tour Guide Debbie LLC has no control of the availability of a site (s) listed in this tour. Tour Guide Debbie LLC will do her best to look for substitute site (s) or activity in according to the tour’s theme.


  • Check-in: Meet 15 minutes before the tour starts.
  • Tour ends: Plaza las Monjas
  • Language: English or español
  • Does not include: Transportation.
  • Group size: Minimum numbers apply.
  • Physical level: medium-low — 2 miles leisure walk on uneven surfaces, flat and steps.
  • Wear comfortable shoes. Bring water.
  • Tour is not wheelchair friendly.
  • Weather: Tour takes place rain or shine.


  1. It is optional to wear mask; however, some locations might require to wear one.
  2. Protocols are according to the guidelines established by the Puerto Rico Government and the Centers for Disease Control.

A 2 hours history walking tour

Since 1998, I have been narrating in storytelling fashion, the history behind the second oldest city in the Western Hemisphere. Exploring historical sites while I talk about the preservation codes that made it possible for Old San Juan is the best preserved 16th Century Spanish Colonial city in The Americas.

«The Story of Old San Juan» 2 hours walking tour includes visiting:

  • interior patios
  • San Juan cathedral
  • the palace of San Juan
  • formal market
  • formal jail
  • Ponce de Leon burial site
  • street corners
  • founding site of second oldest city in the Western Hemisphere
  • cobblestones streets
  • underground burial sites

Looking for a night walking tour consider the «Night Tales in Old San Juan» tour.


available at

Open customer recommendations about www.tourguidedebbie.com

Frequent asked questions

for this tour

Do you provide directions on how to meet with the tour guide?

Yes I do. Please look for the Google map with the meeting location and pictures posted on this page. Plan to be 10 minutes before the tour’s starting time due to COVID-19 protocols. No refund for late arrivals. Expect heavy traffic heading to Old San Juan.

Does the tour includes visiting a fort?

No. The Story of Old San Juan tour is about the colonial city inside the Fortress City.

Is the tour available for independent travelers?

Yes, on selected dates. Please check the calendar.

General Frequent Asked Questions

Join a walking tour at my hometown. You will explore inside historical buildings and learn how to weave a hammock at Puerto Rico’s «18th Century hidden gem» in the West.

Read more

© 2000-2023 Tour Guide Debbie LLC

Call: (787) 605-9060

Users of this site agree to be bound by our
Tour policies and website usage terms

Type of tours
  • Western town in Puerto Rico
  • Battles & Legends in Old San Juan
  • Puerto Rico Rums & Foods
  • Tips for cruise ship passengers
  • Puerto Rico Pasteles
  • Halloween cake with Puerto Rican rum

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Toledo — history you can touch 🧭 tour price €170, 53 reviews, tour schedule in Toledo

Toledo — history you can touch 🧭 tour price €170, 53 reviews, tour schedule in Toledo

fusion of Muslim, Jewish and Christian

Tripster Tour of Toledo

On my auto-walking tour of Toledo you will learn not only the history of the city itself, but of the whole country! Monasteries and churches, palaces and narrow lanes, ancient ruins and museums — from all this variety of architectural monuments in Toledo you will get the image of a truly Spanish city with a special character and destiny.

53 traveler reviews

What to expect

The history of Toledo is the history of Spain. For centuries, Muslims, Jews and Christians managed to live here together. This left an indelible mark on the appearance of the city and its culture. Here, every street, every house keeps the memory of those people who made history.

But perhaps the most valuable thing in Toledo is the atmosphere of «real Spain». And you can see this for yourself.

Panoramic views
All tours of Toledo are walking only. Its medieval streets are completely unsuitable for modern transport. But I suggest starting the tour with panoramic views of the old city. On my car, we will drive along the Valley Road, climb to one of the observation platforms where you can admire Toledo from the highest point.

Main attractions
And after you walk. You will enter the city on one of the oldest bridges in Toledo, the San Martin Bridge. Walk through the streets of Juderia Toledo. See the Monastery of San Juan de los Reyes and the School of the Arts of Toledo, visit one of the city’s synagogues. In the small church of Saint Thomas, see El Greco’s iconic painting, The Funeral of Count Orgas. We will also walk along the “sweetest” street of the old city and see the largest Don Quixote in the world. And then the labyrinths of streets will lead us to City Hall Square — the most iconic square of Toledo. It is here that the Cathedral of Toledo, the main cathedral of Spain, is located: I will tell you about its history and secrets.

Who would like the tour

Both those who came to Toledo for the first time and those who want to get to know the city of «three cultures» in more detail.

Organizational details

How the tour works

  • I will meet you at one of the train stations or in the lobby of your hotel in Toledo
  • Full-fledged excursions are waiting for you in all the sights declared for visiting
  • On Sundays and public holidays it is better to start the tour from 12. 00 (because the Cathedral opens these days at 14.00). With an earlier start of the tour, the visit to the Cathedral will be replaced by a visit to the church of the Monastery of San Juan de los Reyes.
  • Be sure to write what you are interested in — we will take this into account in the program

What’s included and what’s not

  • The price includes the panoramic part of the tour on our car (for groups up to 4 people)
  • Museum tickets are paid separately

The tour is possible for a company and more than 4 people (the cost is discussed separately)

Meeting point

Start of the tour by agreement. You will know the exact meeting point immediately after booking.

Do you have any questions?

Ask questions to the guideYou can chat with the guide before paying for the order and get answers to all your questions

Book an excursion on any of the available days in the calendar companies.

  • On the site you pay 23% of the cost, and the rest of the money — to the guide on the spot. You can ask the guide any questions before paying.
  • Busy day

    Free day

    53 traveler reviews

    Only travelers who have visited the tour can write a review. More details

    Traveler’s photos

    Ivan is a knowledgeable specialist, an excellent storyteller and, of course, a man in love with Toledo! Ivan was very attentive to our needs and problems (one of the children did not feel well in the morning, and we arrived in Toledo in parties), fed, watered and took us to the pharmacy. The most wonderful memories remained from the trip, and the son’s illness passed without a trace under the impression of interesting stories. I warmly recommend the tour with Ivan.


    Many thanks to Ivan for a wonderful tour of Toledo! Fascinating, interesting, at a high professional level. One can feel Ivan’s love for the city, for the history of Spain, attention to detail, deep knowledge. I especially liked the El Greco Museum, where Ivan took me at my request, and the Toledo Cathedral (a whole world full of jewels). The tour was longer than we expected, and yet it was a pity that it ended, I wanted to continue. But that’s next time. Highly recommend!


    Very interesting tour. Time has flown by imperceptibly. It is very informative and it is clear that Ivan treats Toledo and its history with love.


    My husband and I really liked it! Time has flown by! Ivan is a wonderful storyteller, with a sense of humor, very well-read. Everything was wonderfully organized! A big hello to him from us! We hope that this is not our last meeting and travels to the beauties of Spain are yet to come!!!! Thank you! Sincerely, Oksana, Dmitry.


    I liked the tour very much. Lots of interesting and informative information. In a short time we were able to touch the history of Toledo, see the sights and the cathedral. Many thanks to Ivan for taking care of our stay in the city and helping in ordering a restaurant with great dishes. Very grateful.


    Ivan is an excellent guide, educated and erudite, well versed in the topic. For several hours of walking, it was never boring, a lively story about history and culture


    Wonderful diving excursion. Ivan is an amazing storyteller with deep knowledge of the history, religion, culture of Spain. . We were on the Excursion with our parents — everyone liked it very much, without exception, for each of us, Ivan found something that hooked and remembered. I would like to thank Ivan for the punctuality and comfortable organization of the route. We will definitely be back for other programs.


    Unfortunately, we couldn’t get into the central cathedral. It was closed in the morning for unknown reasons. Thanks to Ivan for a very interesting story about Toledo.


    Great tour. Ivan’s great store of knowledge, accessible presentation of the material, well-planned route allowed us to fully admire Toledo and understand that we are ready to return here again and again! The spectacular finale of the tour in the Cathedral of Toledo is indescribable by the power of admiration and emotions! Thanks Ivan for a great tour.


    Thanks to Ivan for the fascinating story and tour of Toledo.


    2 reviews for other guided tours

    So, a few reasons why this tour is great! )
    Firstly, if you came to Toledo knowing only the general formula about the «city of three cultures» and that Madrid is its successor as the capital, then after the tour with Ivan you will know much more: there are legends, and stories, and that’s it. it is so great to remember and inspires to read historical literature after returning home.
    Secondly, communication with a good person is always wonderful. And when a person talks about what he is sincerely passionate about, it is doubly so.
    Well, a bonus for single travelers like me — you will not be afraid to wander alone through the almost midnight labyrinth of Toledo 🙂
    highly recommended!


    We really enjoyed the tour of Toledo with Ivan, despite the fact that a storm was beginning (partly because he had the foresight to prepare an umbrella and raincoats). Ivan has a wonderful command of the material and told and showed us a lot of interesting things and in general he is a very positive person. We will gladly come back and book another tour with him. Rita, Ofira, Slavik.


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    Frequently asked questions from travelers on tour

    Where does the route start?

    By agreement. You will find out the exact meeting point after making an advance payment.

    Can I ask a question before booking?

    Yes, the organizer will answer your questions within 30 minutes. You do not need to pay, just create an order with a question. If something is not to your liking later, you can cancel the booking · Ask a question

    When can a booking be cancelled?

    Only in case of unfavorable weather conditions, for example, if there is a boat trip, and according to the weather forecast, there is an abnormally strong wind. In this case, the guide will warn you about the cancellation, and we will return the prepayment to the card. In all other cases, the tour will take place.

    Who else will be with me, group size?

    If the tour is private, the guide will hold a meeting just for you and your company. If it is a group tour, there will be other participants on the tour, the size depends on the conditions of a particular tour.

    How to pay for the tour?

    Create a booking for a convenient date and time, and make an advance payment as soon as possible to prevent other travelers from taking your seat. After that, the organizer’s contacts and the exact meeting point will become available to you. Pay the rest of the cost directly to the organizer.
    In rare cases, payment is made entirely on Tripster. Then you do not need to pay the organizer directly.

    If I cancel the booking, will the money be returned?

    If canceled 48 hours in advance or earlier, we will refund the entire deposit. The speed of the return will depend on your bank, usually it takes no more than 72 hours. All other refund cases are described in the refund policy.

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