All I Juanna Do is Explore San Juan with You! Our Weekend Itinerary in Puerto Rico.

“I haven’t been everywhere, but it’s on my list.” -Susan Sontag

Hello Sweet Readers!

I recently got back from a spur-of-the-moment weekend trip to San Juan, Puerto Rico. Spontaneous trips are my favorite kind of trips! My mom and I have always joked that one day we’ll be driving down the road and just decide to keep on going and figure out our destination along the way! My family trips have always been just as much about the journey as the fun we have when we actually reach the destination!

My future sis-in law, Taylor, and I planned this trip to San Juan within a week, for us, her 2 kiddos, and our guys Kevin and Charles, obsessively scouring Airbnb like it was our 2nd job! We finally found the perfect apartment, which went by the name “Ocean View in Old San Juan”, set right in the heart of Old San Juan with a beautiful view of the ocean, ancient forts, and Castillo de Cristóbal right out of our front door for just $110 a night (linked below). You gotta love Airbnb! The place was very nice and clean, and while we actually didn’t end up having electricity for the first day or hot water for the entire trip, the owner graciously refunded our stay. I don’t know about you.. but I’ll take a cold shower for a free stay any day of the week!


Our Airbnb

This trip wasn’t super planned out. We are big adventurers, so we decided it would be fun to play it by ear and explore the city and all of the beautiful sites once we arrived, having a few excursions in mind.

Once we arrived in San Juan, we were able to easily book a rental car for the weekend, as the car rental place was visible from baggage claim in SJU, and shuttles were waiting outside to take you to the other car rental locations close by. We took the shuttle and rented a teenie tiny car from Thrifty Car Rental, which we aptly named Conejo Blanco (the White Rabbit) costing us a total of $150 for the weekend (including toll coverage, which was by all means necessary, for $30).

Not only were there tolls on the highway that cost $50 each time you pass, there was also limited parking available in the city, and if you parked on a side street and were not a resident, there’s a good chance you’ll be met with a $250 ticket. I suggest finding a parking garage and walking when you’re in Old San Juan. We found one parking garage that was close to the Castillo de Cristóbal for around $4 a day.

Castillo de Cristóbal

Exploring the city of San Juan is an adventure of its own. The beautiful, old buildings and blue cobblestone streets really make you feel like you’re somewhere special. Little hole-in-the-wall bars and food vendors sprinkle the streets, where you can find the best empanadas, pinchos, Mojitos and local beer called Medalla, for just a few dollars. Everyone was so nice, and I was worried about getting by with my un poquito Spanish knowledge, but to my surprise, most people spoke or understood English, which made navigating our way through the cities much easier.Plaza De ColónSanta María Magdalena de Pazzis Cemetery

Puerto Rico Vibes

We did hit some not-so-great restaurants while we were there, so with the help of my lovely work friends who are Puerto Rico natives, I’ve gotten recommendations to share with you all on the secret, local gems that are a must try:

1. El Hamburger- this burger place has been open for over 50 years in Old San Juan. While they only serve burgers and fries, they are famous for their food and sometimes have a wait of 40 minutes just to get your hands on one of their burgers! (This instantly reminded me of a special place near and dear to my heart in Aurora, KY, Belew’s Dairy Bar).

2. Parilla Pizzaria Rustica- this was actually a hole-in-the wall restaurant we stumbled upon on our last night in Old San Juan. Not only did this place have some of the best pizza and appetizers I’ve EVER HAD, the atmosphere was rustic and beautiful, filled with art and the smell of Italian goodness.

3. El Callejón de la Tanca– this little dive bar was right by our Airbnb, so we frequented this place for drinks and muy delicioso empanadas, garlic parmesan fries and carnitas tacos. They also had live music playing almost every night!

4. Bebo’s BBQ – this outdoor restaurant was a last minute stop on our way to drop off the rental car, and I’m so glad we did! This was also recommended by a co-worker from PR. Bebo’s serves classic Puerto Rican food with amazing rice that I only wish I could make at home, and delicious sausage and ribs.

Let’s talk excursions- There are so many cool activities and breathtaking sites Puerto Rico has to offer. Everything from night kayaking in the bioluminescent algae and snorkeling, to hiking and zip-lining in the El Yunque Rainforest or exploring Cueva Ventana, and enjoying the many local beaches. Since we only had a few days, we couldn’t do it all, so we chose to go hiking in El Yunque Rainforest, explore Old San Juan, and visit the beautiful beaches.

El Yunque Rainforest The El Yunque Rainforest was definitely our favorite part of the trip. The road leading up the mountain had cute little shops and restaurants, where you can stop and grab a souvenir or taquitos and fried sweet plantains (my personal obsession).

Restaurant on the Mountain

You can also go zip-lining through the rainforest, which Puerto Rico is famous for, as they have the second longest zip-line in the world (recently out-zipped by Dubai). We totally would have done this, but it costs $130 per person, and with 6 of us traveling, you do the math.

The view from the high peaks of the rainforest is indescribable. There is something about the untouched pieces of the earth that leave you breathless in its beauty; endless green forests and flowers, waterfalls bordered the paths leading to more waterfalls and cold, fresh pools. I was hoping to see some wildlife, which I’m sure keeps it’s distance deep in the dense forest.

Yokahú Tower sits in the middle of the forest with 98 steps to get to the top, which was so worth every step because the view was incredible.

We made so many sweet memories on this trip! The kids loved it so much they didn’t want to leave–not even to get home to the dogs! 🐶 I hope you all enjoyed reading about our adventures in Puerto Rico and I hope this is helpful for any of you travelers who are planning or thinking of traveling to Puerto Rico!

Until my next adventure.

With love,

Sweet Maddie Jane

1 Comment

  1. Rhonda Brooks says:

    Loved this Madison!! Your writing just keeps getting better and better ❣️❣️


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