Walking tour of colorful Old San Juan
31 Mar 2019

Walking tour of colorful Old San Juan

Post by Brentsica

We spent a full day in Old San Juan before jumping on our 3:30AM flight to Atlanta, GA…yup, you read that correct, 3:30AM.

The main attraction here are the forts (with breathtaking views of the Atlantic) but Old San Juan is a place best explored by foot so wandering the streets was the highlight for us. It’s an old city in the tropics, you’ll be walking uphill and downhill, so it will be hot and humid.

Note: Old San Juan is one of the most popular cruise ship destinations in the Caribbean. With that said, you should expect a very large crowd if the cruise ships are in. When your cruising on your own boat and use to less people, this can be overwhelming. Boat life has ruined us for sure – lol!

Aside from its 500 years of history, the city is splashed with beautiful architecture and tropical colors. With hours to kill we strolled the pretty blue cobblestone streets, ate and drank our way through the oldest settlement in Puerto Rico!

Total steps: 17,654 


  • El Morro
  • Paseo del Morro
  • Museo de las Américas
  • Casa Blanca
  • Umbrellas on Fortaleza St.
  • Governor’s House
  • Capilla de Cristo (18th century chapel)
  • And more!

Food & Drink: 

  • Princesa Gastropub – highly recommend! We stopped in for drinks/apps and ordered the Almojábanas de Serrano y Manchego. INCREDIBLE! It’s basically a fritter stuffed with Serrano and Manchego Cheese with Guava, Papaya, and Mint Sauce. WOW! They also have a cute rum bar outside.
  • La Guerita – cozy, inexpensive place to enjoy real Mexican food. We got the tacos and Queso Fundido with Chorizo. Try the great variety of hand made hot sauces
  • Chocolato – gelato here really hit the spot! You can add a brownie or shot of baileys to your ice cream/coffee. Unique flavors too.
  • La Taberna Lúpulo – beer selection is outstanding
  • La Bombonera – quaint old time style soda shop that includes a bakery, it’s become a very popular spot with the cruise ships so there was a crowd.
  • La Factoría – the Lavender Mule is AMAZING!! It’s off the beaten path and definitely more of a locals feel.
  • The Mezzanine – Tapas! Ambiance is very classy and old school. We were told that the brunch here is amazing.




Cheers from Puerto Rico! 



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Charlie | The Barefoot Angel April 8, 2019 at 12:18 pm -

Those blue cobble stones are so distinctive!! La Taberna Lupolo is one of our favourites!! Charlie xo

    Brentsica April 18, 2019 at 1:52 pm -

    Thanks Charlie! They are! I kept walking with my head down and was so fascinated looking at them 🙂

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