Traveling Circus Visits San Juan, Puerto Rico

When we lived in Chicago, February was probably the hardest month to get through. With no more holiday festivities to distract from the bitter cold, on some days it felt like winter would never leave! So, we made it a tradition (out of necessity to keep our wits) to find a tropical paradise where the sun was still alive and kicking.
These days, living in Raleigh, there’s little need to get away since winter is milder and easier, but a tradition is a tradition I say! ; ) So this year for our annual winter beach-getaway, after considering our usual spots (Hawaii, Costa Rica, Mexico), we decided on San Juan, Puerto Rico.
Yes, I do remember hurricane Maria, and yes, I do listen to the constant coverage of how things are not yet back to normal for thousands of people on the island. But it only took some research to see that at least in the capital city of San Juan tourism was back on. We took the plunge and booked our vacation, feeling excited and might I add, even a bit noble for choosing a place where our travel money would make a difference, even a small one.
Our 5-day vacation proved that we made the right choice! And so, for our second installment of the Traveling Circus series … I bring you San Juan, Puerto Rico.

Traveling Circus - Puerto Rico



San Juan. Capital of PR. Population just under 400,000 as of 2010 census. Area of 77 square miles.


Hubby, 4.5-year-old daughter, 2.5-year-old son, 7-month old son, and me!

Traveling Circus - Puerto Rico - Raleigh Moms Blog

Getting There:

We flew American Airlines with a layover in Charlotte. The flight from Charlotte to San Juan is right under 3 hours and 30 minutes. Since PR is a territory of the US, passports are not required to travel. However, do make sure to bring children’s birth certificates as ID, as with anytime you fly within the US.

The Luggage:

It is so much easier to pack for a warmer destination. In our previous life of just 4, we would have easily opted for just carry-on luggage. Now however, it’s nice to have the freedom to move about easily (especially with a layover) so we chose to check-in a big bag. Our stroller/carseat were checked in at the gate prior to entering the plane and we had a small backpack with the usual diapering essentials.

Traveling Circus to Puerto Rico - Raleigh Moms Blog


Coloring markers, some chewing toys for Ajay, red dinosaur, and mini construction toys. Markers would have been sufficient but the others came in handy during down-time in the hotel room.

Where we stayed:

I am a self-professed sucker for fancy hotels. Most of the time, the obsession is limited to just admiring them in magazines. This time however, was one of those few times when fortunately our hotel was truly beautiful and luxurious. The Condada Vanderbilt is a gorgeous Spanish colonial style hotel built way back when the Vanderbilts realized PR was a good spot for a fancy hotel. If you follow me on Instagram (@TheAntibland), then you saw me gushing over all the brass and dusty rose in the lobby. Beside the architecture and the hospitality, it was also in a PRIME spot with a huge park next door and lots of eateries within walking distance. We felt very safe no matter when we were out and about. I learned from the concierge that the hotel never closed during hurricane Maria. I think it’s a good idea to stay at a big hotel in this situation, knowing that even if something were to happen, they will have enough generators and man-power to take care of the guests.


Where we ate:

El Vagon was our favorite. It was a bit out of the way from the main drag and has an outdoor patio with the cooking done in a food truck. Kabana was another noteworthy place for dinner. The rest of the restaurants were fine but nothing to write about. In general, there were PLENTY of choices. Our dream to find a whole-in-the-wall taco joint at every corner however, did not come true in the Condado neighborhood.

What we saw: 

Old San Juan is colorful and lively! It is hilly, so beware if you have a stroller, but we still walked around for miles taking turns pushing the stroller up and down the streets. We stumbled upon several beautiful squares with pigeons and fountains to take a break. There is also a free trolley that goes around, but since we had a double-stroller, it would have been more effort to fold and load every time. Plus, we like to walk! El Morro (a national historic site and part of the National Park Service, so take your pass if you have one for free entrance), is one of the biggest and famous forts in OSJ was well worth the time. It had some of the most amazing views of the water. It is a perfect place to fly a kite and picnic too. I imagine though that it gets very hot in the summer months and would not recommend being out there unless it was really early or late in the day. The Museo de Arte de Puerto Rico was another fantastic way to spend an afternoon with the kids. Not only does it have great exhibits, but it also has a well-done children’s zone with coloring, reading, and other activities, and a beautiful outdoor garden filled with sculptors, beautiful plants, waterfall, etc. Bonus: the entrance fee is so much cheaper than other museums I’ve been to! Another neighborhood which we loved is the arts district of Santurce and while it might not be on a typical tourist list of things-to-do, we enjoyed walking around there. In general, we ended up walking about 7-8 miles a day. We also used Uber quite a bit (including getting to and from the airport) which was easy, quick, and cheap.

Traveling Circus - Puerto Rico - Raleigh Moms Blog

What we missed:

The rainforest, which is still closed after Maria. Although, I hear that the clean-up work is almost over and they should be opening soon! There are many museums including the modern art museum which we didn’t have enough time to check out. I also wish we had more time to explore other neighborhoods.

The highest of highs:

Old San Juan for me was so colorful and beautiful. Walking around reminded me of being in Lisbon or Madrid! Luis Munoz Rivera Park was a second favorite with an arboretum, botanical garden, and banyan trees for swinging! The beach. Of course, the beach. I also loved the general vibe from the locals. We saw plenty of local families on playgrounds and on beaches, and it was fun to interact!

Traveling Circus Puerto Rico - Raleigh Moms Blog

The lowest of lows: 

Many times during our trip I forgot that hurricane Maria had ever happened. In fact, most of the time it was not on my mind. But then, while on one of our walks, we’d go through a neighborhood with boarded-up houses or pass a pack of stray dogs. And this was Condado, which is the expensive neighborhood where they worked fast to get things back to normal. I can only imagine how things look in the non-tourist areas and how frustrating it must be to not have the basics in order. Our kids asked several questions about why things looked the way they did, and we did our best to explain mother nature to them without freaking them out! In the end, they were all good conversations and it left us feeling thankful.

Have you traveled somewhere beautiful with your family that left a lasting impact? Please share in the comments below. 

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