When we found out our kids would be out of school for two full weeks this year between Christmas and New Year, we knew we had to get out of Chicago. Travel this time of the year is expensive, especially to somewhere warm, but direct flights to Puerto Rico were available and before we knew it, we were landing in San Juan.
Day 1 – Travel to San Juan
We landed late in San Juan so we just took an Uber to our hotel, Casablanca. It was SO cute though we did have a bit of a snafu when we learned the room we booked didn’t have a single window (yikes). I was immediately claustrophobic. They were able to find us another room that at least had an interior window into the atrium – still not ideal but at 8pm we decided to deal with it for the two nights we were there (attempting to move to a new hotel would have been an increase in cost and a loss in location).
All in all, the staff here was great, the location is fantastic, and the rooftop is incredible. So I do recommend this hotel but be mindful of what you are booking for the window needs!
We snagged at quick dinner at Pirilo Pizza Rustica which had some pretty impressive pizza and good beer. It was one of the few things open late in that area but worth stopping.
Day 2 – Explore San Juan
We had a lackluster breakfast at the hotel (you should definitely go somewhere else to eat if you stay there) and, like I always do, opted for a free walking tour of the city to get our bearings.
This is actually one of the least satisfying walking tours I’ve had. We covered a lot of ground but not necessarily with a lot of unique information. We did stop and get some ice cream at Señor Paleta which had been on my list and it did not disappoint.
Our guide struggled with time management and we ended later than expected – it also didn’t drop us off anywhere near where we started so it was a 15-20 minute walk back. I had meetings in the afternoon (this was working travel!) and we had to skip lunch so I could be back for them. Generally I’m a big fan of these tours to get kick off a city exploration but San Juan might be more conveniently done on your own.
I spent the afternoon working from our rooftop – no complaints there.
We then went to dinner at Cayo Caribe – we were able to sit on the sidewalk to people watch which was nice. We tried our first mofongo – I wouldn’t say this restaurant was incredible but like a lot of San Juan, it was decent enough.
The restaurant was really nicely placed to walk along the Paseo de La Princesa which was all dolled up for Christmas and New Years.
I definitely recommend making this walk along the fortification. It was really neat to be so close to the walls – they were just radiating the heat of the day as we caught a really lovely sunset.
We stopped at Princesa Cocina Cultura just for a drink outside – it seems like typically this place does need a reservation and the waitress seemed a bit miffed that we were only grabbing a drink and people watching but we were early enough in the day that it worked out. The drinks were good and the food looked decent so could be another option.
Day 3 – San Juan -> Arecibo
We woke early to get a little more San Juan under our belts before heading out. We took the advice of our tour guide the day before and went to Cafeteria Mallorca for breakfast. Yikes. We found this overall very underwhelming through it was kind of nice to be at a very clearly local joint. And the mallorca was very light but also super greasy. I feel like there could be better ones out there. I also learned during my time in Puerto Rico that a lot of establishments, even nicer ones, will use disposable plates and utensils. It can make the place and food feel not as elevated trying to cut with a plastic knife on styrofoam.
We walked up to visit Castillo San Cristobal. We were there early so I grabbed a latte at Bien Papayas right on the corner near the entrance. It was so cute but I was served one of the absolute worst lattes I’ve ever had. I literally had to throw it out. Hopefully it was a fluke because wow – it was bad.
The castle though, was a nice little spot to visit. Beautiful views and nice signs explaining it. Your ticket would also get you into El Morro which is typically the more recommended of the two – but we were on a timeline and I enjoyed San Cristobal. I’m sure if you have time for both it’s worth it but if, like us, you needed something closer to where you were staying then this on its own was great.
A quick hike back to our hotel and we checked out then went to pick up our rental car. We took an Uber to the U-Save and became proud (?) temporary owners of Kia Rio. Our rental experience was like any other one I’ve ever had – a little lackluster but overall fine. No reason to avoid this place, especially if, like us, you aren’t picking up at the airport.
We then started our road trip to our airbnb in Arecibo. Along the way we stopped at Manati and the Playa Mar Chiquita. This was a fun little place to stretch out legs and get some great beach feels. If you wanted to, it would be super easy to spend more time here, there was a decent group of people enjoying the sand and sun.
It also had a great restaurant really close by, Costa Azul. I had some really great fish tacos and it was clearly a popular place for some great daily specials.
From there it was another 45 minutes before we rolled into Arecibo and absolutely fell all over ourselves for our perfect our airbnb was. Seriously top notch.
It’s the perfect beach view and is on the top floor so we had our own private rooftop patio with a jacuzzi and everything.
I was able to work from the rooftop with strong wifi that afternoon, it was a dream.
One of the best parts is that it is right in front of what is essentially a private beach! While a little difficult to navigate down the slope, it was so worth it for the incredible sand and privacy.
That evening we checked out a very cute cafe/bookstore called The Bookmark and then went to a delightful food truck spot, Ocean View, for dinner. We stopped by this place SO many times during our week in Arecibo – highly, highly recommend. We can’t say we ate at every truck during our time there but we sampled most of them and I really enjoyed it. It really does have an ocean view with lots of seating.
Day 4 – Exploring Arecibo and around
We rose early to check out Bermudas where I was finally able to find a tasty latte. It was a lovely place with outside seating that was completely overrun by birds. It was both fun and somewhat terrifying?
We drove to find the Cuevas de los Indios but ended up getting there too early. So we parked and took an unmarked path to the beach where we then… accidentally snuck into what was probably private property. Whoopsie.
But it worked out because we were able to see what we are pretty sure was the back of the cave and didn’t need to pay the $10 to get in. Win/win though I won’t be telling you how we did it.
I worked in the afternoon from our outdoor rooftop – no complaints there. Our airbnb bumps up on a truly incredible beach that apparently no one goes on. There are no steps to go down – or there were but I assume Maria was the cause of their destruction – but with a fairly strong hazard to our health we were still able to get down and had a lovely mile-ish to walk all by ourselves. So lovely.
In the evening we headed to what ended up being out absolute favorite restaurant of the trip, Árbore Gastrobar. The service, the space, the food – all of it was excellent. I had a cocktail so glittery it covered my lips like a gloss.
Day 5 – River Caving
This was our most active day yet. We headed out early (when don’t we, honestly) and checked out a River Caving Tour. Our guide for the Tanama river was Edgar and he was great. Really easy going and funny, he did such a great job leading out group which had a family with smaller kids and some not strong swimmers.
This tour was right up our alley. It starts off with a fairly steep decline before you do river walking and floating (some with a decent current!).
You then get to a cave where there are kayaks to take us through it. Then more hiking before a suspension bridge. All in all, super fun, beautiful, and just the right amount of adventure and effort!
We were wiped so a meal at La Guira was necessary. The food was decent – not amazing but it landed pretty well after the good, long hike.
Day 6 – Coffee Farm and Exploring
New Years Eve and we decided to spend our day on a nice loop to explore more of the island. We headed back toward San Juan to visit Hacienda Muñoz. This is a popular coffee farm tour.
It wasn’t our first choice but we were limited by what was open for the holidays. Still it was a nice tour and we got to see the workings of the coffee farm even if the other tourists were a little annoying. Easy to order a cup of coffee though so that was lovely.
From there we drove the Pork Road which was a bit more harrowing than we anticipated. I was randomly navigating us and we were on some very narrow roads up some very high hills and our little Rio was struggling.
There were a lot of options but we decided we wanted to go to one of the most popular, Lechonera El Rancho Original.
Of course I say “we” but I did not come close to partaking. Crispy pig skin is all Eric’s jam, not mine. Top it off with how busy and loud it was and I was struggling, but it was an experience definitely worth checking out.
Thought we would round out our road trip by checking out Ponce but it was a bust. Not sure if the town is still struggling but what we assumed was the downtown area was pretty desolate/abandoned. Restaurants google said were operating were clearly not and had not been for a while. We did find ice cream at King’s Cream but it was just about the only place open on the whole block. Maybe we just missed the good part of the city but it was a bit sad.
New Years Eve at this Airbnb was unbelievably epic. We were on the rooftop at midnight and I’ve never seen so many firework displays at once. It was truly special and sealed Arecibo in my heart.
Day 7 – Rincón
Even for New Years Day we were up and at ’em, this time heading west to check out the surfing city of Rincon. Coffee on the route there was absolutely desolate though and I won’t subject you to the horror that was my styrofoam cup of “coffee”.
Still, we made it to Rincón and found Rincón Paddleboards. There we met up with our instructor, Justin, who took us out for some really nice paddling.
I adore SUP but found the waves were a little too big for my weak stomach and literally got sea sick on a paddleboard. I would have assumed this was impossible, but trust me, it’s not. I toughed it out until we went back in but opted out of the snorkeling portion of the adventure.
Eric had a good time though while I chilled on the beach and watched the waves. Honestly, not a bad trade.
After the drive back we we enjoyed more of our airbnb and, of course, the delightful food trucks.
Day 8 – Back to Work
Officially the first working day of the year but I still was able to grab coffee at Bermudas again before starting the work day.
Eric found a local surf place where they did a day lesson with him which he said was fun. He had done surfing ages ago when he lived in San Francisco so he wasn’t a total amateur. It was a 1:1 class and he was definitely able to tackle some pretty fun waves while I worked.
We did make another stop at The Bookmark because I just loved it. Such a great little bookstore cafe.
For dinner we found La Destileria which was fun and in a part of Arecibo that was really cute, or had been. Again, it was sometimes hard to tell if things were coming back but we really enjoyed this little spot and wished we had gone a little earlier in the day to walk around and explore.
Day 9 – Final Day in Arecibo
We headed to a local spot, Las Delicias, for breakfast. Definitely has a small little diner vibe that worried us at first but the people were exceptionally kind and both the coffee and food were pretty impressive.
I was still working today but did take some time out to visit our local beach even if it I did have to half roll down what felt like the end of the world to do it.
We went back to Árbore for dinner. It was busy and beautiful with all the Christmas lights around the trees. I had the best fish tacos I’ve ever had in my entire life and will never forget. It was the perfect wrap up to our time in Arecibo and Puerto Rico because the next morning we were driving to San Juan to fly out. ❤
Day 10 – Flying home
All in all – Puerto Rico ended up being the perfect escape over the holidays. We were able to easily mix adventure with history with food and work. We learned a lot about this beautiful island that really made my heart ache. I hope we can better support this island and her people and I hope I can go back again sometime. I’m so glad we were able to take the time to explore and stay outside of San Juan.
The Roaming Reader 