2 Days in San Juan, Puerto Rico Itinerary

Are you heading to San Juan, Puerto Rico because you have a cruise booked around the Caribbean Islands? Or do you just want to enjoy the great mixture of the Taino Indian, Spanish and African cultures, the colourful buildings, and the music blasting from the bars and restaurants? Whatever the main reason for your visit, I will show you how you can explore San Juan, the capital of Puerto Rico, in just 2 days. 

About Puerto Rico

Puerto Rico is located to the southeast of Miami, Florida. Just like the U.S. Virgin Islands, the island is an unincorporated territory of the United States. This means that Puerto Ricans can move freely between mainland USA and Puerto Rico. San Juan, the capital city of Puerto Rico is actually the oldest settlement in the US. 

Despite the fact that both Spanish and English are the official languages of Puerto Rico, Spanish is the dominant language that people use in their everyday lives. I enjoy learning and using a country’s native language when abroad. I think it’s important to respect and be aware of other cultures, so make sure you at least say hi, bye and thank you in Spanish. Puerto Ricans are very friendly so all the more reason to learn a few words and communicate with locals.

Hurricane Irma & Hurricane Maria

Both Category 5 hurricanes hit the island in September 2017. We were lucky enough to visit the island and have an undisturbed week of cruising around the Caribbean Islands just a week before Hurricane Irma. (We actually had to evacuate from Florida a week later). Hurricane Maria hit the island soon after Irma and was even more devastating, destroying homes, roads and generating serious flooding! The hurricane affected the entire population of the island!

I consider myself incredibly lucky to have seen some of the amazing Caribbean Islands before the disaster happened. However, 2 years after the catastrophe it seems like the island has slowly recovered (probably not entirely) and tourism is pretty much back to normal. 

How to spend 2 days in San Juan

We spent most of the first day just wondering around the city and admiring the most colourful streets. To really experience the culture, I recommend actually staying in Old San Juan. If you’re a cruise passenger and here for only a couple of hours, the cruise docks in Old San Juan. Here’s the list of amazing things that are easily doable in 2 days:

1. Visit the forts of San Juan

Did you know that San Juan has not one but two forts? El Morro, located at the entrance of San Juan Bay, was built by the Spanish to protect San Juan from attacks from the sea. It was actually the second fort built on the island between the 16th and 18th centuries.  El Morro is a UNESCO World Heritage Site and very popular among visitors. It has a massive, grassed area where you can enjoy a picnic during the day and could come back to watch the sunset in the evening. 

The entry fee is only around $10 but you can visit both El Morro and the other fort Castillo de San Cristobal so make sure you don’t throw away your ticket!

Castillo de San Cristobal is located at the eastern gate of San Juan and was built to guard the city from enemies approaching by land. It’s well worth the visit if you want to have a panoramic view of San Juan and beyond.  

2. Find the most instagrammable streets

Believe me when I say that Old San Juan has plenty of colourful and picture worthy streets. My best advice is to just walk around and explore the area without constantly looking at your map. However, I collected a few very popular ones that you might not want to miss. 

Caleta de las Monjas

This street consists of some amazing colourful buildings leading from San Juan Bautista Cathedral all the way to the water. The cathedral is actually the oldest one in Puerto Rico and the second oldest in the Americas so a must see! Caleta de las Monjas is definitely a street worth strolling through.  

Callejon de la Puerta Bandera

Another popular spot in Old San Juan is the painted Puerto Rican flag door (cover photo) you can find on Callejon de la Puerta Bandera. The surrounding narrow streets are totally picturesque too so make sure you just walk around and explore the hidden gems of the old town.

Calle San Jose

There is a very famous colonial door on an old, abandoned building along Calle San Jose. The door has the Puerto Rican flag painted on it with murals on the wall. The flag that used to be painted the traditional colours of blue / red / white is now painted black and white since 2016 to emphasize the struggle of the country. 

“Under my umbrella ella…”​

I think we all agree that putting colourful umbrellas up along a street is the best way make it insta-famous.  Plus, it’s also a great way to provide people with some shade during the hot summer months. 

Fortaleza Street in Old San Juan has been a well visited street because of its colourful houses and the Governor’s House which is located at the end of it. However, as part of the Umbrella Sky Project the street has now become even more popular with the most colourful umbrellas floating above the buildings. The project’s aim was to bring hope, inspiration or just a smile back to people after the devastating hurricanes. 

As we visited San Juan just before the hurricanes the umbrellas weren’t there. However, if you’re heading there now, I would definitely go as early as possible to snap a few photos.

3. Visit La Fortaleza

Okay, if you came to see the beautiful umbrella street why not walk to the very end were the 16th century governor’s mansion (La Fortaleza) is located. La Fortaleza means ‘The Fortress’ as it was originally built to be one before it was converted to house every governor of Puerto Rico.  It is also part of the UNESCO World Heritage Sites since 1983. You can only go in with a guided tour which is about half an hour long and mainly shows the gardens. 

4. “This is how we do it down in Puerto Rico…”

I think there’s no-one on this planet who hasn’t heard Luis Fonsi and Daddy Yankee’s mega-hit ‘Despasito’. Parts of the video clip were actually filmed in La Perla, a town established in the 19th century and located outside of the northern city wall. For centuries La Perla had a very bad reputation. Even a decade ago visiting this part of San Juan was not advised to tourists and even today I wouldn’t necessarily go there at night on my own. 

The community was taking steps to revitalise the neighbourhood even before ‘Despasito’ was sang by millions. In 2017, private donors raised around $80k to paint around 400 houses with bright colours, giving residents jobs and starting to offer guided tours. However, the barrio definitely became a tourist hot spot after the famous music video. 

You can access the area from 3 points: either from the east side, through a walkway in the city wall or through the Santa Maria Magdalena Cemetery. Whilst you wonder around the barrio make sure you find the 3 iconic spots from the video clip: the rocks facing the sea, the sea wall and the little plaza where locals play dominoes. 

5. Santa Maria Magdalena de Pazzis Cemetery

After you’ve visited La Perla, make sure you check out the Santa Maria Magdalena Cemetery too. Cemeteries are usually not popular tourist spots, but this one is definitely a picturesque one. After all they don’t consider it to be one of the most beautiful cemeteries in the world for nothing. Go and check it out!

6. Plaza Del Quinto Centenario

When you’re exploring Old San Juan, make sure you stop at Plaza Del Quinto Centenario. This square was built in 1992 to honour Columbus’ first voyage to the new land. A tall tower stands in the middle symbolising the origin of the New World. It’s located close to El Morro, so you can definitely visit one after the other. 

7. Bacardi Factory Tour

How to get there?

The cheapest way to get there is by taking the ferry from Old San Juan Pier 2 to Cantona. This cost only $0.50 one way, and it runs every 30 minutes. Once arrived, you can jump into one of the taxis waiting for you and for $3 per person they will drop you off at the factory. 

About the tour

Depending on your budget and the experience you’d like to get, the distillery offers 3 different tours. The cheapest one (the one we took) is the Historical Tour. This only cost $15 + tax and you can get a complimentary cocktail upon arrival. You should arrive at least a good half an hour before you have to join your guided tour so you can enjoy your cocktail. The tour itself will take around 45 minutes and you’ll learn why the bat is the symbol of the brand and get an overview of rum making and the family. If you are a true rum fan or just want to splurge a bit more, you can join either the Rum Tasting Tour or the Mixology Class to master your cocktail making. 

If you have a little longer…

Visit El Yunque Rainforest

If you’re a nature lover, you have to visit this tropical rainforest which is actually the only one in the United States. You can find plenty of hiking trails and can chase some waterfalls. Unfortunately, we didn’t have enough time, but it gives us a reason to return to Puerto Rico. 

Chill on a beach

There are tons of amazing beaches around Puerto Rico so if you’re staying on the island longer make sure you explore them. Some, however, are located close to San Juan like Escambron, Playa Pena, Condado or Ocean Park Beaches. Both Playa Pena and Escambron Beach are actually walking distance from Old San Juan so definitely check them out if you have some time to get a nice tan or enjoy the palm trees and a sunset. 

Final Thoughts on 2 Days in Puerto Rico

2 days in San Juan was just enough to fall in love with Puerto Rico. I really hope that in the near future I’ll be able to return and explore more of the island. Have you been to Puerto Rico before? How much of the island did you manage to explore? Let me know in the comments below.