Caribbean My Travelz Puerto Rico

A Few Hours in Old San Juan, Puerto Rico

There is so much to do in Puerto Rico as a whole you could be there for weeks exploring every nook and cranny. In Old San Juan alone you could be there for a few days really getting into a little bit of everything. Although I didn’t do that, I was still able to get a nice little smattering that made me want to go back and visit again.

Stepping foot out of the taxi in Old San Juan, we were all immediately smacked in the face with heat and humidity. A beautiful sunny day that felt slightly gross. We spoke with a lady who was sitting out on one of the streets selling tours, but the tours she was offering seemed a bit overpriced so we began walking around exploring. The heat got to us quick and we learned there was a free trolley that rolled around the entire area, so we hopped on that.

Old San Juan ©2017 HollyDayz

Free trolley ©2017 HollyDayz

Riding around with a nice breeze and some shade we got to see many of the different highlights of Old San Juan, the colorful buildings, the beautiful ocean, Carmelo Anthony’s basketball court, and more. We also passed by the cruise ships docking in, San Cristobal, and San Felipe Del Morro. Hunger soon struck so we got off and began walking around doing some shopping and decided on a place for lunch.
Carmelo Anthony’s Court ©2017 HollyDayz

Around San Cristobal ©2017 HollyDayz

After lunch we walked around a bit more and then took a spin back on the free trolley. Seeing some other sites we missed before hopping off to eat. Such a beautiful place Old San Juan is. The trolley helped get a bearing on where things were and how far was one thing from another. We got off and roamed around again. It was nice to stop and get some pina coladas while people watching.
Having some fun ©2017 HollyDayz

Love the views from El Morro ©2017 HollyDayz

After walking around a bit more we were done with Old San Juan for the moment. I would happily go back to see and do more. Old San Juan is beautiful and I loved the sights and sounds of it all.
Have you been to Old San Juan?

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  • Bon-Bon

    Beautiful pictures!!! I just published my latest blog about PR:) You went there lately? Why too short? You have to go back and if you need some help, I would be glad to connect you to some people with the tourism Board ( I was the speaker during the Road SHow). Beautiful island and deserves a lot of praise… People has to know!!! Please email me anytime… xoxo

    • Holly Dayz

      Thank you so much! I haven’t been as of late. I just took a quick day trip. I def need to go back and would love to be connected!

  • Tamara Elliott

    I definitely need to get back here- we visited once right before a cruise, but arrived late at night and then it was pouring rain the next day, so we didn’t see any of it!

    • Holly Dayz

      That rain is what really messed it up huh….that stinks.

  • hcura

    I haven’t been but would love to. Really pretty place, so colorful! Thank you for sharing.

    • Holly Dayz

      I hope you get to soon, it was such a beautiful place.

  • Priya Vin

    Haven’t been to PR, but we have it on our list of places to visit soon! Old San Juan looks so colorful and a quaint place to visit

    • Holly Dayz

      I hope you get there sooner than later. I need to go back.

  • Noel Morata (@emorata)

    I love visiting historic districts in different places and Old San Juan looks so colorful and that fort is so immaculate, was it rebuilt?

    • Holly Dayz

      It is so colorful with beautiful views. I didn’t hear that it was.


    I haven’t been to Puerto Rico at all. Old San Juan looks stunning – the kind of place I’d like to stay

    • Holly Dayz

      It is beautiful. I need to go back and also see more of Puerto Rico.

  • tracy collins

    I know very little about Puerto Rico – it isn’t somewhere I had even considered visiting until I started reading more about it! It is lovely to read about and see pictures of beautiful places around the world that aren’t familiar to me.

    • Holly Dayz

      Def a place you should visit.I need to go back myself.

  • SherianneKay

    I’ve heard really good things about Puerto Rico and have wanted to go for some time now. Would love to wander the old town, and that water is such an amazing blue!

    • Holly Dayz

      I loved the views. I want to go back..hopefully soon.

  • Claudia

    Ohh this article came at the right time.. I havent been to Puerto Rico in 5 years… and the last few weeks I have been missing it so much! And now I am even more nostalgic… it might be time to book a trip!

    • Holly Dayz

      It is a sign that you should go back soon.

  • Rob

    We have been to San Juan only once before, stopping there on a cruise. This was many, many years ago. I am pretty sure they didn’t have a trolley back then, if they did we totally missed it. It certainly would have made our visit easier as we wanted to check out as much as we could before the ship left port.
    I would love to go back and experience the old town again.

    • Holly Dayz

      It would have been great had there been one or had you known about it, you would have certainly liked it. You should go back. I know I will.

  • Sara Broers (@TravelWithSara)

    I love strolling the streets of Old San Juan. The cobblestone streets and colorful buildings are beautiful! I have been several times on a cruise stop and will definitely go back on a cruise or a visit to the island.Old Town offers so much, history, culture, foodie lover’s paradise and a fun place to people watch. I had no idea they offered a free trolley, I’m making note!

    • Holly Dayz

      I love the cobblestone streets. They have a blue color. The free trolley was great.

  • Indrani

    It is a charming place. One week of slow travel around these places should be ideal. I haven’t got the luck to get there yet… hope travel God gets a little kind with me!

    • Holly Dayz

      I would like to slow travel a bit around PR.

  • Trisha Velarmino

    The pastel-colored establishments in that alley look very Instagram-worthy! Glad you enjoyed your short but sweet stay in Old San Juan! Xx

    • Holly Dayz

      I did enjoy it and need to get back.

  • Buddy The Traveling Monkey

    I spent a weekend in San Juan and like you said, could easily spend more days exploring. I didn’t realize there was a free trolley though! That would’ve been nice instead of walking in the humidity everywhere! lol

    • Holly Dayz

      Def more days could be used to explore. The trolley is a life saver because that heat and humidity was no joke.

  • Keisha Adinkra

    I have been seeing so many gorgeous pictures of Puerto Rico! I will take it as a sign and add it to my list of places to visit. Sometimes short stays are the best! Glad you enjoyed yourself and thanks for sharing.

    • Holly Dayz

      It is such a beautiful place. I look forward to going back. I hope you do go it should def be on your list. I enjoy short stays sometimes.

  • MUAKimPorter

    I love Old San Juan, aside from it being rich in history, there are some amazing restaurants in the area.

    • Holly Dayz

      The food was great. I would happily go back and eat some more.

  • feleciamonique88

    I haven’t been! But I would love to. Looks beautiful and fun. Great post!

    • Holly Dayz

      Thank you. It is such a nice place.

  • Mimi Green

    I love old San Juan, although I’ve only been once I made the most of it. I would love to go back, there are several things I didn’t get to do while there.

    • Holly Dayz

      I would love to go back myself. There is so much to see and do.

  • staciesayzso

    Beautiful place! I love how blue the water is. Looks like you had an awesome time!

    • Holly Dayz

      I loved how blue it was.

  • Jo

    I LOVED San Juan. My sister and I spent the day in Old San Juan for food & the historic site. I didn’t even know there was a ferry to go to the Bacardi Factory there. Definitely a nice place to go for a family vacation. Good weather, good food and no passport required. Everyone has a good time.

    • Holly Dayz

      I don’t blame you. Yup, I knew about the ferry just didn’t go. I think the highlight for many is no passport.

  • Latoya Scott (@lifeandabudget)

    Oh my, this is absolutely beautiful. I haven’t been there but my eye is on it now!

    • Holly Dayz

      Yes, put it on the list and go when you can.

  • That's Chelsea

    I love San Juan! Next time you are in the area, try to pop over to Isla Verde Beach.

    • Holly Dayz

      There is a ton of places I want pop over to on that island lol. I will def put that on the list.

  • Daria

    OMG! These pictures make you feel as if you are there. Just absolutely beautiful. I’m long overdue for a vacation and this would make an awesome one. The water is just stunning…I’m dreaming of one now, lol…Soon and very soon. Thanks for sharing!

    • Holly Dayz

      Thank you so much. I feel you, time to go back.

  • Carissa (The Green Eyed Lady)

    The pictures are beautiful!!! I would love to see this in person! Adding to my list of places to visit NOW!!

    • Holly Dayz

      Thank you. Yes, you must and I hope you get there soon.

  • Kiwi

    I did Carnival Cruise last year and I had a few hours in Old San Juan. You got way more of the experience than I did so thanks for your recap!

    • Holly Dayz

      How was the cruise? Maybe next time you will get some more time to explore.

  • Ty

    I need to get to Puerto Rico. It is on my bucket list and your pics confirmed that I need to get there soon!

    • Holly Dayz

      Yup you need to go. That was just one area of all the beauty.

  • cleverlychanging

    Puerto Rico is one of my favorite places. I love their culture and architecture.

    • Holly Dayz

      It is beautiful so I understand that.

  • Aanchal Iyer

    Had heard lot about Puerto Rico, but looking @ the images and the visit you had to this lovely city is fantastic seems you really had a fun. I love the colorful houses out there looks pretty pleasant and attractive. Wish to visit there soon.

    • Holly Dayz

      I love the colors and the views as well.

  • Fabi

    Nice photos! This place is definitely on my travel list!

    • Holly Dayz

      Thank you. I hope you get to visit soon.

  • Tia | Pennies In My Pocket

    I have not yet visited Puerto Rico but it is definitely on my list for this year. I was considering a cruise but I do not like only being in port for a few hours in each destination. This post is great for a brief cruise stop in San Juan so maybe I will reconsider.

    • Holly Dayz

      I would like to go back myself. Do some more exploring. Getting a little bit of exploring in is better than none at all.

  • Travelen

    Beautiful pics!! Useful info..!

    • Holly Dayz

      Thank you!

  • Therie

    Is San Juan a pretty walkable city? because it looks like one of those cities that you’ll get to know more if you explore it on foot. Thanks, Holly!

    • Holly Dayz

      Yea it is walkable. I enjoyed the trolley. Learned what I am looking at and can get off and walk around. It is like being on a hop on hop off bus.

  • Amarante

    I love San Juan, great place to have a good coffee and read a good book at a terrace. Hablo espanol, helps much to visit the city and get to know the authentic. Nice blog. Cheers

    • Holly Dayz

      Thank you. I know some Spanish, not fluent, but don’t have to know it unlike some other cities where it was more important to know it.

  • Jessica M

    Old San Juan is one of my favorite places in the world. Been there tons of times but didn’t know Carmelo had a court there! My hubby is a huge BB fan, he’s going to want to go there next time we’re in PR.

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