Four Days in San Juan, Puerto Rico

Puerto Rico has been an unincorporated territory of the United States since 1898 after the Spanish-American War. San Juan is the capital and largest city of Puerto Rico located on the northern coast of the island. San Juan was established in 1509 when Spaniards colonized the land. This beautiful city is rich in history and culture and should be on everyone’s bucket list. I had the opportunity to spend four amazing days in this gorgeous city and had an incredible time! I share my experiences below, along with my itinerary and other recommendations I have for visiting the island.

Things to Know Before Your Trip

  • Climate: Puerto Rico has a hot and humid tropical climate year-round. December through March is the dry season on the island with average temperatures of 70 to 83 °F (21 to 28 °C). April to November is the wet season, so it is often hot and humid with increased rainfall. The average temperatures during this time are 77 to 89 °F (25 to 32 °C). Hurricanes usually occur during August and October but the official hurricane season lasts from June to November.
  • Language: Spanish and English are the official languages in Puerto Rico, but Spanish is, by far, the dominant language spoken on the island.
  • Currency: Puerto Rico uses the United States dollar (USD) as their form of currency.
  • NOTE: You do not need a passport to visit Puerto Rico if you are a United States citizen.


There are so many places to stay at that it was tough to figure out the best option. We were trying to save as much money as possible, so we decided on staying at an Airbnb. There are so many hosts in San Juan that it made it very easy to find a place that suited our needs. You’ll be able to find luxury or budget-friendly options. For our stay, we had originally planned to stay at this Airbnb for the central location and low price, but there was some miscommunication and we had to switch our stay to another Airbnb. While we did end up spending more for the new location, it was right next to the beach and was easy to get to Old San Juan, so we weren’t too upset about going over our budget and, in the end, we absolutely loved our stay with Ronaldo. The apartment was everything we needed, and he was an excellent host. I definitely recommend staying with him!

Also, if you’re new to Airbnb and would like to receive a travel credit for your first stay, sign up with my invite link! You can get up to $40 off your first stay and $15 off your first experience booked through Airbnb.

If you prefer to stay at hotels or resorts, there are plenty to choose from. You can easily find great resorts right on the beach, so that way you’re only steps away from tropical paradise. If you know that you’re going to be spending a lot of time exploring Old San Juan, you would be better off booking a place there instead since the beaches are a bit further away from the historical center. Some of my hotel recommendations are Condado Vanderbilt Hotel, La Concha Resort, and Hotel El Convento. These come with a larger price stamp than Airbnb, but they provide incredible accommodations and easy access to the best tourist destinations in San Juan.


There are very limited options to get around the island. The metropolitan San Juan area has a public transportation system but it is not the most reliable (aka buses are not on time). Their public bus system is called Autoridad Metropolitana de Autobuses (AMA). Regular fare for a bus trip is $0.75, which makes them the most cost-effective way to get around the city if you’re on a tight budget. You can find the bus routes on their website, but there is no official schedule that I could find. You can also find more information on public bus fare prices here.

San Juan also has one active train line named El Tren Urbano that runs from Bayamón to Sagrado Corazón. The rail line is 10.7 miles long and has 16 stops. If you’re along the train route, this could be a faster way of getting around San Juan. Each train trip costs $0.75, so it is also an affordable transportation option. For more information on El Tren Urbano’s route and operating hours, check out this website.

My main mode of transportation was taking Ubers or walking to our destination. As of now, Lyft is not available in San Juan, so there was not much option but to take Ubers everywhere. Thankfully, Ubers are very affordable in Puerto Rico. We spent less than $12 per Uber trip to get around San Juan. If you plan on staying in Old San Juan the entire time, walking around would be best since that area is very walkable and the narrow streets make driving more difficult. If you’re planning on visiting other parts of the island, I definitely suggest you look into car rentals. It would be the most convenient and cost-effective way to travel the island.

If you’re new to Uber, you can get $2 off your first 3 rides by using my code jennifera32ui.


Day 1

We landed in San Juan’s airport (SJU) in the early evening and took an Uber to our Airbnb. We had communication issues with our host and were not able to check in there, so we ended up canceling our reservation and booking another Airbnb on the spot. It was a bit of a stressful situation, but we made the best of it and ended up with a fantastic Airbnb in the end. This Airbnb was located in the Ocean Park neighborhood and was right next to the beach! A huge win for us!

After checking into our Airbnb and unpacking our things, we headed to a nearby restaurant, La Cueva del Mar, for dinner. This restaurant is known for its delicious seafood dishes. It was recommended to us by our Airbnb host and we were not disappointed. I ordered some spinach and cheese empanadas and Mario ordered the black tuna wrap. The food was SO delicious and we loved the drinks, too. We really loved this place because it has a bar, and there are many TV screens playing sports games. It’s the perfect place to eat at to unwind after a long day.

Day 2

On our second day, we explored Old San Juan and walked through all of the colorful buildings. You could easily spend hours just walking around. There is so much to see! For lunch, we ate at La Barrachina, the birthplace of the piña colada. It would be a sin to go here and not order some piña coladas… so we did, and they were probably the best piña coladas we’ve ever had. I also ordered the vegetable mofongo, and Mario ordered the Supreme Burger. Mofongo is a staple Puerto Rican dish and is incredibly delicious! It was my first time trying it and I instantly fell in love. If you’re ever on the island, you have to try some.

It was super hot that day (like every day), so we decided to cool down with some paletas from Señor Paleta. Super yummy treat! They sell lots of flavors and it’s one of the best paleta shops in San Juan. You have to check them out!

Paleta de coco from Señor Paleta

After that, we took a little break by the pier before catching a ferry from Old San Juan to Cataño, Puerto Rico. We had booked a guided historical tour of Casa Bacardí, the largest rum distillery in the world. The San Juan distillery produces 85% of the world’s rum! I thought it would have been so expensive to visit a place like this, but it was actually very affordable and included a cocktail with your tour.

Before your tour starts, you can lounge at their outdoor bar and patio. There are many places to sit and enjoy a drink. You can also take in the beautiful scenery and take photos at their Casa Bacardí barrel sign. Once the tour starts, everyone gets into a tram that takes you to the location of your tour. During the tour, the guide explained to us the history behind the creation of rum and how the company was formed after the owner, Bacardí, used a new distillation method to create his world-famous rum. During the tour, we were also able to view the production machinery, visit a replica of Bacardi’s office, see the company’s historical artifacts, and smell the various types of rum they created, too. The historical tour cost $15 each, but they also offer rum tastings and mixology classes. If you’re interested in learning more or booking a tour, check out their website. It was a really fun experience and one of the highlights of our trip!

Fun fact: Apparently, pirates were the first major consumers of alcohol (for “medicinal purposes,” of course) and they invented the mojito hundreds of years ago, too.

Day 3

On our third day, we spent most of it in Old San Juan again. The first thing we did was Uber to Castillo San Cristóbal. We spent a couple of hours exploring the historical site and learning about the colonization of San Juan and how it was affected by those many wars on its land. It was an incredibly educational experience and very important to learn about the impacts colonization had on indigenous people. Aside from it being very educational, the castle is right next to the ocean so it has beautiful views everywhere you look.

When you purchase admission to Castillo San Cristóbal, you also get access to Castillo San Felipe del Morro, aka El Morro. Tickets cost $10 for adults for a full day of access to the two sites. Admission is free for children under 15 years old. For more information, check out the National Park Service website.

After visiting Castle San Cristóbal, we ate breakfast at La Wafflera. I had the s’mores waffles and Mario had the Elvis ones. Yes, they were very, very sweet and overpriced. I’m not sure if I would go back there to eat because it didn’t live up to my expectations, but it was still a nice place to eat at for some waffles.

After breakfast, we explored a little more of Old San Juan before heading to El Morro. It was very similar to Castillo San Cristóbal but still very beautiful and worth the visit.

After visiting El Morro, we spent the rest of the day at Ocean Park Beach. It’s a lesser known beach, so it wasn’t very crowded. We were able to sip on some wine and enjoy the beautiful rainbow that appeared over the water. We also saw one of the prettiest pink sunsets at this beach before we left. This was definitely our favorite beach! It’s a lot smaller than El Condado Beach, but I prefer avoiding the crowds when possible.

Day 4

As you may have already guessed, we spent another day exploring Old San Juan. Trust me, there is so much to see in such a small space. We spent a lot of time walking through the streets but I know there is still lots we didn’t get to see. One of the best places we visited was the Puerto Rico flag door. It’s a huge garage door painted with the Puerto Rican flag. It’s so stunning, like all of San Juan!

Calle Fortaleza is the street that leads to La Fortaleza, the official residence of Puerto Rico’s governor. Usually, Calle Fortaleza has rows of umbrellas over the street, but during our visit, the umbrellas were replaced with a giant Puerto Rican flag. I can’t deny that I was excited to see the umbrellas, but the Puerto Rican flag looked just as amazing, as well.

After getting tired from walking around, we ate lunch at Deaverdura in Old San Juan. This restaurant honestly makes some of the best rice I’ve ever had. It was one of the more affordable restaurants we ate at, too! For delicious and authentic Puerto Rican food, definitely check out Deaverdura.

We went to El Condado Beach after eating. It’s right next to a hotel strip so there were many tourists there, but that’s not always such a bad thing. The beach itself was a lot bigger and cleaner than Ocean Park Beach. There are also more restaurants and street food in this area. The hotels also provided a lot of shade in the afternoon which was an unexpected perk. We were close to one of the hotels that was playing music so that made our beach day a lot more fun. Overall, I really liked the beach and wish I was able to spend more time there. If you’re trying to tan, though, it would be best to go in the early afternoon because the hotels block a lot of the sunlight later in the day.

Side note: I saw a street vendor selling piña coladas at one of the entrances to the beach, so you should definitely take advantage of that!

Day 5

On our last day of the trip, we had to pack up all of our things and carry them with us throughout the day. Our flights were scheduled for 3 AM the following day, and since we didn’t want to pay for an extra night at our Airbnb, we just decided to carry our stuff instead. Thankfully, we only brought a backpack each since it was a short trip, so we didn’t have too much of a hassle.

We ate lunch at Pirilos in the Ocean Park neighborhood. Our Airbnb host told us that they had some of the best pizza in Puerto Rico and he wasn’t lying! Shoutout to Ricardo for the recommendation. They had the best veggie pizza and spinach empanadas! I would definitely go back to this restaurant. We loved the food so much, we went back to another Pirilos for dinner that night before catching our flight back to Chicago.

During our free time, we walked through El Paseo del Morro, which is a long pathway along the edge of San Juan and El Morro. It’s right next to the beach so we just strolled the entire path and enjoyed our last sunset in Puerto Rico. We really loved walking here, but something to note is that there are a lot of stray cats that have found a home in this area. If you’re allergic to cats, this may not be the best place to visit. If you’re a cat lover, then I think you’ve found your paradise because there are dozens of cats here. Either way, it’s important to note that most of these cats were abandoned by their owners after Hurricane Maria hit. I can’t recommend that you feed them or try to pet them, but there is a volunteer organization, Save A Gato, that works to medicate, feed, and sterilize the cats. You can check out their website to learn more about them and to donate, as well.

This was one of my favorite trips of all time. We only saw a small portion of what Puerto Rico has to offer, so I definitely want to go back someday. If you ever get the chance, I say book a flight to San Juan because it is one of the most beautiful places filled with incredible culture and history. Trust me, you won’t regret it!

Thank you so much for reading! Leave me a comment down below if you liked my blog post or if you’re planning a trip to San Juan soon.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s