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?

66 thoughts on “A Few Hours in Old San Juan, Puerto Rico

  • April 1, 2017 at 11:40 am
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    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

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    • April 11, 2017 at 10:44 pm
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      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!

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  • April 1, 2017 at 11:51 am
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    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!

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    • April 11, 2017 at 10:45 pm
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      That rain is what really messed it up huh….that stinks.

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  • April 1, 2017 at 12:31 pm
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    I haven’t been but would love to. Really pretty place, so colorful! Thank you for sharing.

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    • April 11, 2017 at 10:46 pm
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      I hope you get to soon, it was such a beautiful place.

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  • April 1, 2017 at 1:07 pm
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    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

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    • April 11, 2017 at 10:47 pm
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      I hope you get there sooner than later. I need to go back.

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  • April 1, 2017 at 1:25 pm
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    I love visiting historic districts in different places and Old San Juan looks so colorful and that fort is so immaculate, was it rebuilt?

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    • April 11, 2017 at 10:48 pm
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      It is so colorful with beautiful views. I didn’t hear that it was.

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    • April 11, 2017 at 10:48 pm
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      It is beautiful. I need to go back and also see more of Puerto Rico.

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  • April 1, 2017 at 2:35 pm
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    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.

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    • April 11, 2017 at 10:51 pm
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      Def a place you should visit.I need to go back myself.

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  • April 1, 2017 at 4:24 pm
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    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!

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    • April 11, 2017 at 10:52 pm
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      I loved the views. I want to go back..hopefully soon.

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  • April 1, 2017 at 4:48 pm
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    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!

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    • April 11, 2017 at 10:56 pm
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      It is a sign that you should go back soon.

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  • April 1, 2017 at 5:45 pm
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    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.

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    • April 11, 2017 at 11:02 pm
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      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.

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  • April 2, 2017 at 3:26 pm
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    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!

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    • April 11, 2017 at 11:05 pm
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      I love the cobblestone streets. They have a blue color. The free trolley was great.

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  • April 4, 2017 at 12:22 am
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    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!

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    • April 11, 2017 at 11:09 pm
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      I would like to slow travel a bit around PR.

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  • April 4, 2017 at 3:52 pm
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    The pastel-colored establishments in that alley look very Instagram-worthy! Glad you enjoyed your short but sweet stay in Old San Juan! Xx

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    • April 11, 2017 at 11:12 pm
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      I did enjoy it and need to get back.

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  • April 4, 2017 at 10:08 pm
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    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

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    • April 11, 2017 at 11:14 pm
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      Def more days could be used to explore. The trolley is a life saver because that heat and humidity was no joke.

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  • April 5, 2017 at 11:36 am
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    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.

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    • April 16, 2017 at 10:24 pm
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      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.

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  • April 5, 2017 at 6:36 pm
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    I love Old San Juan, aside from it being rich in history, there are some amazing restaurants in the area.

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    • April 16, 2017 at 10:25 pm
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      The food was great. I would happily go back and eat some more.

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    • April 16, 2017 at 10:25 pm
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      Thank you. It is such a nice place.

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  • April 6, 2017 at 9:11 am
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    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.

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    • April 16, 2017 at 10:26 pm
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      I would love to go back myself. There is so much to see and do.

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  • April 6, 2017 at 10:44 am
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    Beautiful place! I love how blue the water is. Looks like you had an awesome time!

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    • April 16, 2017 at 10:27 pm
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      I loved how blue it was.

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  • April 6, 2017 at 10:58 am
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    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.

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    • April 16, 2017 at 10:30 pm
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      I don’t blame you. Yup, I knew about the ferry just didn’t go. I think the highlight for many is no passport.

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    • April 16, 2017 at 10:31 pm
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      Yes, put it on the list and go when you can.

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  • April 6, 2017 at 1:45 pm
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    I love San Juan! Next time you are in the area, try to pop over to Isla Verde Beach.

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    • April 16, 2017 at 10:32 pm
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      There is a ton of places I want pop over to on that island lol. I will def put that on the list.

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  • April 6, 2017 at 1:58 pm
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    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!

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    • April 16, 2017 at 10:51 pm
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      Thank you so much. I feel you, time to go back.

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  • April 6, 2017 at 7:52 pm
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    The pictures are beautiful!!! I would love to see this in person! Adding to my list of places to visit NOW!!

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    • April 16, 2017 at 10:52 pm
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      Thank you. Yes, you must and I hope you get there soon.

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  • April 7, 2017 at 1:37 am
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    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!

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    • April 16, 2017 at 10:53 pm
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      How was the cruise? Maybe next time you will get some more time to explore.

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  • April 7, 2017 at 2:11 am
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    I need to get to Puerto Rico. It is on my bucket list and your pics confirmed that I need to get there soon!

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    • April 16, 2017 at 10:53 pm
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      Yup you need to go. That was just one area of all the beauty.

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  • April 7, 2017 at 8:35 am
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    Puerto Rico is one of my favorite places. I love their culture and architecture.

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    • April 16, 2017 at 10:54 pm
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      It is beautiful so I understand that.

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  • April 13, 2017 at 5:41 am
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    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.

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    • April 16, 2017 at 10:54 pm
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      I love the colors and the views as well.

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  • April 16, 2017 at 5:03 am
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    Nice photos! This place is definitely on my travel list!

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    • April 16, 2017 at 10:55 pm
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      Thank you. I hope you get to visit soon.

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  • April 17, 2017 at 12:31 am
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    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.

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    • April 22, 2017 at 11:22 pm
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      I would like to go back myself. Do some more exploring. Getting a little bit of exploring in is better than none at all.

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    • June 17, 2017 at 9:58 pm
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      Thank you!

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  • May 13, 2017 at 8:48 am
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    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!

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    • June 17, 2017 at 10:01 pm
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      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.

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  • May 30, 2017 at 1:01 pm
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    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

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    • June 17, 2017 at 10:02 pm
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      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.

      Reply

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