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Old San Juan Best Kept Secrets Tour

San Juan, Puerto Rico

Check local COVID-19 restrictions before booking

Experience hosted by Andy

2 hours
Up to 10 people
Hosted in English

What you'll do

- We will be exploring the 500 year old walled city of Old San Juan, discovering secret corners and little-known spots full of charm and steeped in history, that remain unnoticed to the casual visitor. We will walk through Old San Juan’s blue cobblestoned streets, accompanied by a knowledgeable local architect, learning about how the city was built in this rocky island jutting out to the sea, observing the urban layout, constructive methods and architectural details of the Spanish colonial buildings and defensive structures. In this 2 hour stroll you'll experience historical architecture with an insider, not just as a tourist, since we will be visiting private residences, convents and places with limited access. You'll have a chance to peer into underground cisterns, wonder at frescoed chapels, climb rooftops to explore hidden towers, and basque in secluded Spanish patios.
Other things to note
Tour leaves SHARP at departure time. Please allow extra time to find parking and meeting location. Participants need to check in 10 m before tour starting time. If you are interested in tour dates not in the calendar, please inquire about availability.
- We will be exploring the 500 year old walled city of Old San Juan, discovering secret corners and little-known spots full of charm and steeped in history, that remain unnoticed to the casual visitor. We will walk through Old San Juan’s blue cobblestoned streets, accompanied by a knowledgeable local architect, learning about how the city was built in this rocky island jutting out to the sea, observing the urban layout, constructive methods an…

Andy's commitment to safety

This host committed to Airbnb’s COVID-19-related safety and cleaning guidelines—including adhering to social distancing guidelines, practicing good hygiene, and ensuring that all participants wear a mask.
Learn more
From $25
/ person
Mon, Jan 18
10:00 AM - 12:00 PM
Join 4 other guests
$25 per person
$25 per person
Wed, Jan 20
10:00 AM - 12:00 PM
$25 per person
$25 per person
Thu, Jan 21
10:00 AM - 12:00 PM
Join 5 other guests
$25 per person
$25 per person

Meet your host, Andy

Host on Airbnb since 2018
  • 1595 Reviews
  • Identity verified
Through my work as an architect, I've come to appreciate the fine classical tradition in many of Puerto Rico’s historic buildings, in the layout of its towns, and the clever design of its old homes. The quality and rich detail of our small island’s historic architecture, which spans across 500 years of history is impressive. Concerned by how little known our architectural heritage is to outside visitors and even to the locals, in 2011, I founded a nonprofit, volunteer-based institution focused on educating the public about Puerto Rico’s spectacular historical environment.
Through my work as an architect, I've come to appreciate the fine classical tradition in many of Puerto Rico’s historic buildings, in the layout of its towns, and the clever design of its old homes. The quality and rich detail of our small island’s historic architecture, which spans across 500 years of history is impressive. Concerned by how little known our architectural heritage is to outside visitors and even to the locals, in 2011, I founded a nonprofit, volunteer-based institution focused o…
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About the organization: Puerto Rico Historic Buildings Drawing Society



Puerto Rico Historic Building Drawings Society—PRHBDS—is a private Puerto Rico-based nonprofit organization founded in 2011, with the mission of educating the public about Puerto Rico's history and architectural heritage, and creating awareness of the need for its preservation. Our digital collection of 5000 documents, measured drawings, historic images, and maps are available free of charge.

This is a social impact experience where 100% of what you pay for this experience goes to Puerto Rico Historic Buildings Drawing Society.

Where you'll be

We will be in historic Old San Juan, a walled city located in an islet in San Juan Bay, exploring 5 to 7 historic structures, including centuries old churches, private residences, and rooftops, among other best kept secrets of the oldest city under the American flag. You will go beyond the usual touristy experience, hand in hand with a local architect, experiencing the spectacular historic architecture of this world- heritage site.

Rated 4.97 out of 5 from 1595 reviews.

Ehren
January 2021
Exceptional tour. We learned a ton about this city, particularly the architecture and the history. This is a beautiful part of the city, we were shown some unique vantage points and learned a lot about how it came to be. Very friendly & personable and his English is great which is fortunate cuz our Spanish, we're finding, is not.
Exceptional tour. We learned a ton about this city, particularly the architecture and the history. This is a beautiful part of the city, we were shown some unique vantage points an…
Dane
January 2021
Andy was amazing. Rather than giving you the “Disneyland” side, he tells you the honest truth of old San Juan, it’s history, architecture, and current challenges. His eye for detail and intimate knowledge of the town makes you feel like you grew up here. Highly recommend.
Andy was amazing. Rather than giving you the “Disneyland” side, he tells you the honest truth of old San Juan, it’s history, architecture, and current challenges. His eye for detai…
Colten
January 2021
I really felt like I got to know Old San Juan in its purest form. Andy did a phenomenal job explaining the history and taking the moment to make moments uniquely personal for all of us. I feel like I know and can explain Old San Juan through a more experienced lens and I can’t wait to go on more adventures here in the future.
I really felt like I got to know Old San Juan in its purest form. Andy did a phenomenal job explaining the history and taking the moment to make moments uniquely personal for all o…
Romie
January 2021
Based on the reviews, I had super high expectations...and Andy did NOT disappoint. I believe that taking a tour with a local should be done in any place, but especially a place with as much history as San Juan. Andy is filled with content knowledge and the ability to connect with the guests. Learning about the architecture in Old San Juan doubled as a history lesson. Now I will always look at Spanish colonial style buildings in a new way. We made some friends on the tour too. Everyone was friendly and we asked Andy a ton of questions!
Based on the reviews, I had super high expectations...and Andy did NOT disappoint. I believe that taking a tour with a local should be done in any place, but especially a place wit…
Javier
January 2021
Andy was amazing. First time to PR and will definitely be coming back. Safety measures were always a priority and Andy was a great tour guide.
Michelle
January 2021
WOW I absolutely loved Andy’s expertise and guide points to be able to fully appreciate the history of Viejo San Juan, and I will definitely go again to get the most of his knowledge and insight. Do this!!!

Choose from available dates

22 available
1 / 2
  • Mon, Jan 18
    10:00 AM - 12:00 PM
    Join 4 other guests
    $25 per person
  • Wed, Jan 20
    10:00 AM - 12:00 PM
    $25 per person
  • Thu, Jan 21
    10:00 AM - 12:00 PM
    Join 5 other guests
    $25 per person
  • Fri, Jan 22
    10:00 AM - 12:00 PM
    Join 3 other guests
    $25 per person
  • Fri, Jan 22
    1:30 PM - 3:30 PM
    Join 2 other guests
    $25 per person
  • Mon, Jan 25
    10:00 AM - 12:00 PM
    $25 per person
  • Mon, Jan 25
    1:30 PM - 3:30 PM
    $25 per person
  • Tue, Jan 26
    1:30 PM - 3:30 PM
    Join 2 other guests
    $25 per person

Things to know

Cancellation policy

Any experience can be canceled and fully refunded within 24 hours of purchase, or at least 7 days before the experience starts.

Guest requirements

Up to 10 guests of all ages can attend.

What to bring

We suggest guests bring Water, sturdy walking shoes, sunblock, hats, shades, an umbrella.