Devouring Old San Juan, Puerto Rico (walking food, historical + architectural tour)

Today, we're in Old San Juan, Puerto Rico. We're actually staying about 30 minutes east of here, but we had to come into town to try some of the top sites and bites in the oldest city on U.S. soil. So let's start devouring on this walking food tour!

Contents

0:00 Intro
0:12 Plaza del Quinto Centenario
0:45 Cafe Don Ruiz
2:17 Castillo San Felipe del Morro
4:28 La Tortuga
6:10 La Factoria
7:47 Puerta San Juan
8:20 El Jibarito
9:57 Chocobar Cortés
12:55 Python Detour
13:56 Barrachina
15:15 Princesa
18:42 Conclusion

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ABOUT US.

We’re the Lockwoods: a family with 3 kids, 5 careers, and endless passion for adventure. Two years ago, we decided it was time for Phil's ad agency to abandon the in-person, 5-day workweek. So they 86’d the office and work hours, allowing our own family to start traveling almost constantly. We now work, school, and explore in a different place every week—from our own mountain and beach homes to exotic villas, resorts, and yachts around the world. As we experience and support diverse cultures, we hope to inspire more families to design a life of freedom and adventure.

Because there’s a new American Dream. It’s one that’s void of templated expectations, templated career paths, templated education, templated families, templated homes, and templated lives. Freedom is no longer an American tagline—it’s just the new, global way of life.

Every day that you spend doing something that doesn’t fulfill you to your core, you’re living your life on pause. You’re deferring genuine family time with no guarantee that there will be a tomorrow or a someday. Some people follow that mentality their entire lives. We’ve chosen to never live that way again.

We appreciate you following our journey. The more our channel grows, the more time we can spend traveling to more locations, contributing to these cultures, highlighting local businesses, and sharing inspiring stories from these communities. So please consider liking, commenting, and subscribing so that you can stick with us for the long haul.

[amgooder]

Great narrators🎤Old San Juan a true gem💎
Always remember to mix the rice with beans, beans are like the sauce it adds
flavor to rice🙂

[skylane]

I Love that the whole family is traveling together and enjoying all that yummy food, drinks and all the historic sites. If you get a chance you must visit Fajardo and definitely go to the Bio-bay…that will blow your mind and the kids will love it. Also, try Toro Verde zip lines in the town of Orocovis. So much to see and do in that little gem of an island. Thank you for sharing your video.👍👍👍👍

[marangelialmodovar]

What you ate at El Jibarito IS NOT A TAMALE, THAT IS A PASTEL. Tamales are Mexican and made with corn in a corn leaf. Our pastel is made out of cassava, taro root and/or green banana like the one you ate, wrapped in banana leaves. They are both delicious but made with totally different ingredients and from totally different countries.

[evelynrodriguez]

Thank you for sharing the video with us there's no place like our 🏝 island Puerto Rico it's a Paradise ♥

[wendyjenkins]

hi family i was in puerto rico caguas, ponce, bayamon and san juan food yum beautiful places you guys looks so cool having so much fun be safe

[anthonicelauriston]

I love this video!! As a foodie, I can truly appreciate how much food and drink you all devoured in this video, while still doing a walking tour w/ the kids!!!
Added bonus is the kids (who are super cute btw) give their reviews. Your son might be my favorite! Him eating the rice while u gave your review was gold!!

[Indianinthemachine]

That montage at the cool bar of Erin talking and Phil almost drinking, was hilarious. Extra good energy all around from everyone, even the snakes.

[chaselex]

The kids giving food reviews is honestly great haha good points

[heatherwhitehead]

Thank you for showing something other than just bars. You hit some great family spots.

[shtmetal]

Great video. I can tell those drinks were definitely feeling those drinks

[justmelscorner]

Cool video, great family and thanks for sharing! Just one comment, the bread is pronounced, mah-Yor-kah. The double L has a 'y' sound. :)

[eyesea]

La Factoria bar scene was really cute!! Caraffee 😂 You hit such beautiful and obviously tasty places, I'd love to go there sometime.

[americangirlNJ]

Your kids are well spoken .. kudos to you guys 😊

[vexx]

Well spoken knowledgeable visitors thank you for visiting my homeland with grace and respect you earned a new sub!

[gtanguma]

Your family is beautiful and everyone looks like their having lots of fun!

[Montanez]

You guys are so amazing!😊❤ Congraulations on a very delightful and splendid and highly sophisticated video.❤❤😊

[danielagiraldo]

Oh my god! Your kids are the cutest thing ever and I find amazing that you included them in the video, like a very fun family activity 💙💙 new subscriber here! Wish all the success ✨✨

[kristadiaz]

We are heading to PR tomorrow on our second Inspirato trip! Your videos were super helpful when we were deciding to join! If you are still on the island try Mofongo con churrasco! It’s all I eat while there 😂

[ShaneJBurke]

Great video we loved it !!! Puerto Rico 🇵🇷 ❤️

[rowenaibanez]

Nice video, so informative, new subacriber here from the Philippines.