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  • Writer's pictureBecky Wagaman

Exploring Old San Juan, Puerto Rico

Updated: May 27, 2021

For Dustin’s birthday this year, I wanted to do something special. He is always going all out for mine (like a year and a half ago for my 30th birthday when he booked us a room on the Grand Canal in Venice to celebrate), so this year, I planned something big! I knew how much Dustin has been itching to get to the Caribbean on our own boat and seeing how we can’t afford one just yet, I figured I would do the next best thing, and booked a surprise cruise to 6 different islands in the southern Caribbean! This way we could get a taste of the islands and see which ones we wanted to come back to on our own boat someday.

It was so hard keeping this a secret from him for so long and I had planned to wait until his actual birthday in February to tell him, but finally, I had to spill the beans. He kept trying to make plans for us to go on a trip to northern Michigan with his mom at the same time that we would be on the cruise so it was getting too stressful trying to keep it a secret. Plus, we had to choose which shore excursions we wanted to do at each island and I thought it would be more fun for him to be able to plan it all with me, instead of me just choosing by myself.

Around Christmas last year, I thought up a fun way to tell him what his present was going to be. I set up a scavenger hunt around our house with one word clues that had to do with our trip and hid them for him to find. I purposely made the clues hard so he wouldn’t figure it out just yet. Since it was Christmas, I had purchased an ornament shaped like a cruise ship and nestled it in the middle of our “Travel Tree”- our Christmas tree that we decorate each year with ornaments that we have purchased throughout our travels (we get a new ornament from each place that we visit). So as the last clue, I told him to find the new ornament on the tree. When he found the cruise ship, I handed him a guidebook to the Caribbean with the pages marked for all of the islands that we would be visiting and told him what his gift was. He was really excited and I was so happy to finally not have to keep it a secret!

2 months later, just after Dustin’s birthday, we flew to San Juan, Puerto Rico which is where we would embark from for our cruise.

That’s a good day right there…. Dustin, an airplane that was

taking me somewhere tropical and Starbucks!

As we were going in for a landing in San Juan, the airplane suddenly sped up, pulled upwards, and turned around. We could see the runway that we were supposed to land on out of our window as we turned. Everyone was a little perplexed until the pilot came on the intercom and announced that we had been too close to another aircraft so we had to turn back and do a circle before landing! Luckily, a few minutes later, we happily landed.

As we waited for our luggage, it was more fun than usual because they had the baggage claim painted like a game of Roulette, so we made some playful bets on which one our bags would end up on. We were both wrong!

After collecting our luggage, we headed outside to find a taxi. SJU was very organized with how to acquire public transportation compared to most airports. The city was divided into 5 zones and there was a flat rate determined by the government depending on which zones you traveled between. They had an organized line to wait in and asked where each person was going and then would escort them to a taxi based on which zone that taxi was heading to.

They also charged $1 per piece of luggage and charged a couple of other nominal fees. For Dustin and I along with 4 bags and the fees, it only cost us $26 total for a 15-20 minute ride from the airport to Old San Juan. Shuttle services were significantly more expensive (up to $40 per person) so we felt that this was a good deal!

I had booked us a room at the Sheraton Hotel in Old San Juan directly across from the cruise ship piers for ease of access the next afternoon. The hotel was really nice and had a great view of the ships coming and going. There was also a rooftop pool!

Our hotel across from the harbor

After checking in, we went to the hotel restaurant called Palio and sat on the outdoor patio overlooking the harbor.

We enjoy trying local foods when we travel so we ordered a Puerto Rican sampler along with two cups of plantain soup. All of the food was great but the soup was amazing! The sampler included hummus with plantain chips, mozzarella and tomatoes, chicken chicharrones (which is a Dominican version of fried chicken with spices) with pineapple sauce, and queso frito (fried cheese). All of which was washed down with a refreshing glass of sangria, which then made me start singing “Sangria” by Blake Shelton.

After dinner, we decided to walk around Old San Juan a bit by night. It is only 7 square blocks so it doesn’t take long to walk from one end to the other, but it is jam packed with character and charm. The old Spanish architecture there is gorgeous! My favorite style of architecture is clay roofs and stucco walls and Old San Juan had an overabundance of it! We walked along the water’s edge until we came upon a band playing some Latin music in the streets. People were dancing and singing along and everyone was having a great time! We stopped and enjoyed the energy for a bit and then kept walking to see more of the town in our short time there.

We ended up on Paseo de la Princesa, which is a lovely walk through the city and along the city’s massive outer wall.

Along this walk we passed by a beautiful fountain called “Raices” which is supposed to represent the city’s cultural roots.

Soon we arrived at the City Gate.

At this point we had the choice to enter the gate into the city blocks or to keep walking along the path to El Morro Fort. However, the path was closed off for some reason so we went through the gate and explored the city by night.

Around every turn there was more charm! Such a quaint city and chocked full of history! On the way back to our hotel, we stopped at a vendor and got two of the best piña coladas I’ve ever had in my life! The fresh pineapple and coconut made such a big difference compared to home!

The PROPER way to serve a piña colada!

The next morning we had a few hours before we had to check in on the ship so we decided to explore the city a little more in the daylight. Our hotel was kind enough to hold our luggage for us while we walked around, which was so helpful! I really wanted to see the forts up close so we walked to the closest one, Castillo de San Cristobal.

On the way in the one of the town squares, we saw a man performing some sort of Cirque du Soleil type of act. It was neat how the city was so full of life and entertainment! The streets were full of music and performing acts!

A couple blocks up, we reached the fort. This fort was built in 1634 and was used to protect the city from invasions. It sits perched atop a hill on the Atlantic side, just to the right of the city.

We didn’t want to pay to go in as we only had a short amount of time, so we took a few photos from the outside and then continued along the road until we reached the other end at El Morro Fort. There is an expansive grassy field in front of this fort that was filled with kids flying kites.

We stopped to take a few photos and then turned back to go to our hotel to pick up our bags. There was a pharmacy right next to our hotel and we had overheard some people talking about how the cruise ships allow people to bring on board a bottle of wine along with a 12 pack of pop. Since these beverages were not included on the ship, we decided to buy some and take our chances and see if that was in fact, true.

After grabbing some last-minute items at the store, we walked across the street and made our way to the check in line for our cruise ship, Carnival Fascination!

We decided that Puerto Rico is definitely a place we would like to return to so that we can visit more of the island. There are mountains and rainforests and bioluminescent bays and tons of beautiful beaches and scenery that we didn’t have time to explore so hopefully one day we can go back and spend a week or two just in Puerto Rico!

View photos of our ship in the next post!

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