Private Tour of Old San Juan

Discover Old San Juan’s hidden gems with a private tour. Explore forts, plazas, and cafes at your own pace. Feel like a local.

Duration: 4 hours
Cancellation: 1 day learn more
Highlights
  • Old San Juan - We will tour the city
  • Plaza Colon - At the entrance of Old San Juan, featuring a statue of Christopher Columbus.
  • Castillo de San Cristobal - Impressive! The largest fort built in the Western Hemisphere. We can explore some of its hidden secrets like tunnels, dungeons, military strategies, and more.
  • La Perla - An interesting community outside the city walls, where the “Despacito” video was filmed. We’ll view it from above.
  • Plaza del Quinto Centenario - Built in 1992 to commemorate the 500th anniversary of the encounter between two worlds. We can stop and take pictures.
  • Tótem Telúrico - A fascinating monument honoring our prehistoric ancestors.
  • Iglesia de San Jose - Built in 1532, it is considered one of the oldest churches in the Western Hemisphere. It was recently restored. Let us know if you want to see the interior.
  • Plaza de San Jose - Features a statue of Juan Ponce de Leon.
  • Calle del Cristo - Believed to be one of the first paved streets in the Western Hemisphere. Part of Old San Juan’s shopping district and home to some of our most important historic buildings.
  • Catedral Basilica Menor de San Juan Bautista - Let us know if you want to go inside. Considered the oldest cathedral in the Western Hemisphere, built in 1521. It houses the remains of Juan Ponce de Leon (our first Governor) and our landlady.
  • Hotel El Convento - Our first nunnery (1652) is now a high-class hotel. Let us know if you want to go inside.
  • La Puerta de San Juan - Once the main entrance into the city and the Western Hemisphere.
  • La Rogativa - A monument honoring the women who repelled the British invasion of 1797.
  • Capilla del Santo Cristo de la Salud - A chapel honoring a miracle that supposedly occurred in 1753.
  • La Fortaleza - Palacio de Santa Catalina - The oldest executive mansion in the Western Hemisphere, still in use.
  • Calle del Cristo - Known as “Umbrella Street.” A popular photo spot as the First Lady often hangs umbrellas.
  • Plaza de Armas - Our main town square.
  • Casa Alcaldía de San Juan - San Juan City Hall.
  • Departamento de Estado de Puerto Rico - Puerto Rico State Department.
What's Included
  • Private transportation
  • On-board WiFi
  • Certified professional and local guide
  • In-vehicle air conditioning
What's Not Included
  • Food and drinks
  • Extra fee fro Pickups outside of the SJ Metro Area (Rio Grande: $80, Dorado: $100)
Additional Information

Experience San Juan in the best possible way with a private tour. Focus on what excites you the most. Discover the history and hidden secrets of this amazing place, and explore the forts, churches, plazas, cafes, museums, and local flora and fauna. It’s not like a college lecture; it’s more like spending time with a knowledgeable local. Feel like a local as you walk at your own pace, taking breaks whenever you wish. Enjoy a fantastic day in San Juan, Puerto Rico!

  • Please send me your phone number, so I can get a hold of you the day of the tour.
  • Children must be accompanied by an adult
  • At time of booking, Cruise ship passengers must provide the following information at time of booking: ship name, docking time, disembarkation time and re-boarding time
  • Dress code is smart casual. Bring comfortable shoes. Be prepared for a hot/sunny day, and possible rain.
  • It is recommended that you bring a hat, and sunblock. and plenty of drinking water
  • Operates in all weather conditions, please dress appropriately
Location
Old San Juan
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.9
(71 Ratings)
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Paulanf6768wk
Dec 23, 2021
Wonderful Day In Puerto Rico - Javier was a wonderful guide, planning an interesting day for my whole family ages 12 to 52 on our first trip to Puerto Rico. He is extremely professional and exceptionally knowledgeable.
Review provided by Tripadvisor
E7313zdadamj
Aug 4, 2021
Great walking tour. - Fantastic waking tour of Old San Juan. Our guide Christian was super knowledgeable, but most importantly easy to get along with and really relaxed. We ended up having lunch together at the end of the tour. This is a great option if you want to go a little deeper into the history of PR in general, and especially if you want to have candid discussions about the current state of affairs in PR, and broader discussions that are not available on a cookie cutter tour. My kids were pretty engaged the whole time, which speaks volumes. Definitely recommend a private tour.
Review provided by Tripadvisor
Karen_h
Jun 22, 2021
Old San Juan tour - Javier was right on time and was very knowledgeable. He kept a pace that we were all comfortable with. We thoroughly enjoyed our tour.
Review provided by Viator
Beachcommuter
Apr 18, 2021
Great start to Puerto Rico vacation - Javier was wonderful. Very knowledgeable about a wide range of the history of Puerto Rico, architecture, religious heritage, as well as many current political and social issues. He is clearly passionate about giving a great experience. We enjoyed our walk of Old San Juan and sipping pina coladas with him at Barachina. We even got to see his home while on the tour. Highly recommend.
Review provided by Tripadvisor
Ects_southpaw
Feb 24, 2021
Amazing tour guide and person! - Javier is by far the best guide in Old San Juan. We heard this from local passers by all throughout our tour. He is highly educated too. We benefitted from his amazing knowledge not just of the city and its buildings but of the historical events that shaped the city, its political framework and cultural aspects too. Javier guides with a refined yet very laid back approach. We never felt rushed and he didn't end the tour right on the clock. He has a lovely and warm demeanor and is a genuinely sweet guy. We loved him! It should also be noted that he charges per tour and not per person! He is much more affordable than his agency tour operator competitors. Highly recommend.
Review provided by Tripadvisor
415dbrown
Dec 29, 2020
Wonderful tour guide - Javier was delightful! Very knowledgeable and professional but not boring. It was a well worth the money. Old San Juan is beautiful. We will be back!
Review provided by Tripadvisor
109anastassial
Mar 12, 2020
Wonderful tour & incredible guide - Our tour with Javier could not have been better. We loved his honesty, insight, and passion. He took us all around the old town of San Juan and explained the history of the city and people of Puerto Rico in a seamless and entertaining way. When we went to certain historical sites, Javier gave us an overview and also gave us time to explore a bit on our own. Javier was down to earth and did not make us feel stupid when we had a "stupid question", which was so refreshing. At the end of our tour, he gave us a bunch of recommendations for places to eat and local bars, and we had great experiences at the ones we went to. Everyone in our group said that they loved Javier's tour and we all would hire him again the next time we come to San Juan! 10 stars if I could give it!
Review provided by Tripadvisor
J9546qoandreal
Feb 7, 2020
Amazing day! - I can not say enough great things about our day with Javier! We had one day in San Juan and were traveling with our 12 year old so needed a combo of history and little bit of fun to keep our son engaged. Javier couldn't have been a more amazing guide! He knew just when my son was zoning out and would loop him back in with fun facts only a 12 year old could appreciate, which we as parents appreciated! Javier is so kind and thoughtful, he wanted to make sure we were enjoying the day and not also over loading us with too much info (the man is a walking wikipedia and I am sure could talk for hours on just about any subject). He brought us to places we may not have found on our own as well as made sure we saw sights that were more touristy. I have to chuckle at the other reviewers comment about being too political, it is sort of hard to cover the history of an area with out addressing some politics! LOL we did not find Javier in anyway to be "too political", he was mindful and thoughtful of whatever came out of his mouth and was a wonderful guide! We were sad when the day was over and hope we will meet him again! He also gave us a great dinner recommendation which was a local place that had very delicious food! PS - he is also a unicycling champ, which my son was so excited to hear all about as he just started unicycling so Javier gave him lots of great tips and even a quick demo!
Review provided by Tripadvisor
Travasb1
Jan 24, 2020
Active Family - If you don't want to take pictures from a window then Javier Ruiz is the guide for you. During this journey you see the world through a locals eyes, the good bad and ugly. This is where history met adventure, and the diversity in locations kept the family of 5 busy the entire time!
Review provided by Tripadvisor
Globetrotting807623
Jan 18, 2020
Wonderful Tour with Javier - We had a great tour of San Juan with Javier. The city is just beautiful and I can't imagine anyone better than Javier to see it with. His passion for the city and its people is infectious. I particularly appreciated his deep knowledge of history and current social and political events. This was not just "look that way" but a real immersion into this lovely old city. See San Juan and see it with Javier!
Review provided by Tripadvisor
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September 2024
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