#1 Food Tour in Puerto Rico – TripAdvisor

Walking History Tour™

Take a stroll through time and appreciate today’s incredible architecture and landmarks in Old San Juan, Puerto Rico


Tour Type

2 hours


10+ landmarks visited

history, walking tour


Per Adult
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A smart and simple way to learn about and explore Old San Juan is with a local, knowledgeable guide who will lead you on an easy 2 hour history stroll through the oldest section of the city. Following the tour you will understand the history behind the Commonwealth of Puerto Rico, its unique ties to the United States as well as its rich Spanish, Taino Indian and Western African heritage. 

Perfect for all ages, this history walking tour will explore landmarks such as La Casa Estrecha – one of the narrowest houses in the Western hemisphere; La Catedral de San Juan Bautista – Old San Juan’s venerated cathedral is Puerto Rico’s grandest religious building, and one of its most important, as well as parts of the city’s impressive defensive system, namely its walls, only remaining entrance door (La Puerta de San Juan) and Fortaleza, the fort “mistake” the Spanish made! Our tours also visit La Rogativa, La Capilla de Cristo and many more “do not miss” sites.

Join us on this thorough walking tour, uncovering this 500 year old city in a fun, informative way.

  • Photograph incredible Spanish colonial buildings while learning their backstory

  • Enjoy Old San Juan, a UNESCO World Heritage site, with an informed, entertaining bilingual local

  • Stroll the cobblestone streets of this 500 year old fortified Spanish colonial city and find out why they are blue

  • Go inside the city’s venerated cathedral and the island’s grandest religious building and one of its most important


  • Ditch the map for a personally guided tour with an expert

  • Off the beaten path areas featured on tour with insider knowledge

  • Learn about our architecture, historic landmarks, history and other lesser known tidbits

  • Bilingual, knowledgeable guide provides more color and context than solo walking

Frequently asked questions

Yes! Private tours are perfect for birthdays, bachelorette/bachelor parties, family trips, team building, ice breakers, honeymooners, corporate adventures and more! Private tours are based on availability. Please see our Private Tour Page and send us a request.

Our Old San Juan Food Tour provides samples of food and drink, enough for most people to feel comfortably full afterward.

*Participants must be 18 years or older to drink alcohol in Puerto Rico.

The Old San Juan Food Tour does NOT end in the same location as the starting point, but it is around the corner and we can provide assistance if necessary after the tour to get you to wherever you need to go.

*NOTE* the end and beginning of the Old San Juan Food Tour is only a few blocks away from the cruise ship docks.

Please be sure to check the LOCAL TIME in Puerto Rico. Puerto Rico observes Atlantic Standard Time and does NOT use Daylight Savings Time.

Flavors of San Juan is NOT responsible if you are late to a tour because you are unaware of the local time zone.

Have more questions?

Visit our full FAQ page

Walking History Tour™

Duration: 2 hours

Location: We meet at 206 Calle Tetuan (corner Calle Justo and Calle Recinto Sur) at the Plaza de Rafael Carrion in front of Old Banco Popular in Old San Juan facing the Bay of San Juan. Your guide will be wearing a green shirt and a smile.

Dress Code: We’ll be visiting various churches and their dress code rules include “no revealing items of clothing.” Please use your best judgment and bring along items that can help cover exposed chests and wear the appropriate length of shorts/skirts.


Adult age 10+


Child ages 3-9
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