A long weekend in San Juan, Puerto Rico: the perfect itinerary

A long weekend in San Juan, Puerto Rico
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A long weekend in San Juan is enough to soak in a lot of what Puerto Rico has to offer. More time is always better, but we only had three days and it was a great introduction to this beautiful Caribbean island. 

We decided to make it a quick weekend getaway because we found really affordable flights on SkyScanner. Yet, San Juan and its surroundings surprised us with lots of history, colonial architecture, great beaches, mountains and even a rainforest.

Below are all the details from our three day itinerary. But first, I am also including a summary of everything you need to know before arriving on the island. 

What to know before going to Puerto Rico

  • Puerto Rico has been a U.S. territory since 1898. This means you can find everything on the island and you will need U.S dollars. Walmart, Walgreens…you name it, they have it. Don’t worry too much about packing all the essentials.
  • If you are an American citizen, you won’t need a passport. Any valid form of ID is enough.
  • Both English and Spanish are official languages, but Spanish is the dominant one. Speaking Spanish is highly appreciated by locals.
  • DON’T rent a car to move around San Juan. Traffic jams are serious and parking is very limited. You can Uber or take a Taxi everywhere, it will save you time and money. Trust me, this is speaking from experience. Only rent a car for the days you are venturing out of the city.
  • Puerto Rico is safe! I always perceived it as a dangerous island, and I think the media has a lot to do with that. We felt pretty safe walking around at all times, even at night. Like with any other place you visit, be careful, though
  • The food is delicious, but get ready for fried everything. It takes its toll. 
  •  It’s a Caribbean Island, which means it’s always beach season there. Also, all the beaches in Puerto Rico are public!
  • Hurricane season is real. Officially, there are risks of major hurricanes from June to November. However, you are more likely to see them from late July to late September. Puerto Rico is known to have seen some pretty strong ones, so keep that in mind when planning. 
  • Yes, the bar from the viral song Despacito is in San Juan and so is the video location. Make sure to check it out during you long weekend in San Juan.
What to wear in Old San Juan Puerto Rico
One of the many colorful buildings in Old San Juan

❤ Outfit details: Romper | Straw Bag | Bag Tassle

Where to stay in San Juan, Puerto Rico

If you only have a long weekend in Puerto Rico, I recommend you base yourself in the capital, San Juan.

You will probably see some recommendations to stay in either Old San Juan or Condado Beach. These are both popular, touristic, crowded and expensive areas.

If you want to experience the real San Juan, stay away from the tourist traps. We found a very nice Airbnb in the Ocean Park area, and I can’t recommend it enough. There are great local restaurants around and the beach is only a 5 minutes walk away!

You have 3 days in San Juan, what to do?

We arrived in San Juan late Thursday night and flew back late Sunday night, which means we had three full days to explore Puerto Rico. Here is a summary of our long weekend itinerary. More details, photos and alternatives below.

  • Day One – Explore Old San Juan & afternoon at Ocean Park Beach
  • Day two – Day trip to El Yunque & Luquillo Beach/ Night out in San Juan
  • Day three – Bacardi Rum Factory/Calle Loiza/Afternoon at Condado Beach

Day One – Explore Old San Juan & afternoon at Ocean Park Beach

Morning exploring Old San Juan

Old San Juan is lovely, colorful and very charming. On our first day we had a fun morning walking around and exploring the area. You don’t need a serious itinerary to soak in the beauty, as you will find pretty streets and plazas everywhere. Here are some of my favorites landmarks, all within walking distance from each other.

Fortaleza Street: Charming cobblestone street that leads to the Governor house. This is in the heart of Old San Juan and it’s a great place to start your day. There was an “umbrella project” ceiling there, but it was replaced by a Puerto Rican flag by the time we visited in February 2020. Lots of restaurants and shops around. 

Fortaleza Street Old San Juan Puerto Rico
Puero Ricans are very proud of their flag, you will find them everywhere!

Pigeon Park (Parque de las Palomas): Only a 5 minutes walk from Fortaleza street. The park swarms with pigeons, and it’s a nice and clean area with great views of the bay. Bring some cash to buy food for the pigeons. If you are not a fan of the birds, it’s still worth a visit to see both kids and adults alike having fun with them.

Pigeons at Pigeons Park in Old San Juan
Can you tell it was fun?

Barrachina Restaurant: Home of the first Piña Colada! This bar is also only one block from La Fortaleza street. If it’s too early for a drink you can come back later. Overpriced but worth a visit.

Barrachina Restaurant Home of the Pina Colada
Barrachina, birth place of Piña Colada

Calle San Jose: This is another pretty street; famous for its iconic wall with a black and white Puerto Rican flag door. The flag had the original colors (red, blue and white), but it was changed in 2016 as a way to emphasize the struggles of the country. You can find the Puerto Rican Flag door approximately ½-block off (south) of Calle San Sebastián, right across the street from La Factoria Bar. It was a meaningful find for us as Cubans, the Cuba & Puerto Rico flag are almost identical. Our histories are also quite similar.

Puerto Rican Flag Door San Juan

Castillo del Morro/Castillo de San Cristóbal: There are two forts in the city, built when Puerto Rico was a colony of Spain. If you feel like you have time you can visit both. If you only visit one, you should go to the main one, El Morro. We did not enter any of the castles, but I highly recommend at least a walk around the main one. You can also walk around the ample and well-maintained green area outside. We saw people flying kites, having picnics and just enjoying the stunning views of the ocean.

Castillo del Morro Puerto Rico
Green area leading to El Morro
Puerto Rico Outfit Ideas
The Caribbean sea is right next to the fortification

Views of La Perla: La Perla is a shanty town located right next to el Morro. It has a bad reputation as a big drug area. Okay, I realize this might be a weird recommendation! I figured I was going to put it in here just in case anyone is as interested and thrilled as I was to see La Perla. Lots of famous Puerto Rican songs I grew up listening to make reference to this neighborhood, and I understand why. I was fascinated by the colorful houses and the view that those living there get to enjoy everyday: the stunning Caribbean sea.  

Anyway, if my recommendation is not weird enough, this next part might be. You can see the neighborhood from the street right above it which leads to the El Morro Castle. BUT! you get a much better view of La Perla from the east corner of the Old San Juan Cemetery. For me cemeteries are not attractive, and this was my first time actually entering one. I know in many cities these are huge tourist attractions and many people consider them peaceful…but I just find them creepy.

You can also go directly to the neighborhood. I’ve read the area has improved a lot, but I wouldn’t recommend you do so, just in case. 

Views of La Perla from the Old San Juan Cemetery
Views of La Perla from the Old San Juan Cemetery. Notice the other castle in the background.

Relaxing afternoon at Ocean Park Beach

Since we were staying in Ocean Park, we decided to go back and spend the afternoon by the beach.

Ocean Beach was quiet, but if you are not in the area, a local friend also recommended Playita del Condado. Other nice beaches you can go to include Cerro Gordo or Mar Chiquita (about 40 min to get there) or Pinones. People like Pinones because it is supposed to have a very local Puerto Rican feel. There is a new place there called Drift that seems to be getting a lot of attention.

We finished our long and fun first day with a delicious dinner at Pirilos Pizza Restaurant. Food was good and it is conveniently located right next to our Airbnb. Try their “Pirilo” pizza, with ground beef and ripe plantains. That’s a Puerto Rican classic.

Ocean Beach San Juan at sunset
Ocean Beach during sunset, so quiet and relaxing

As an alternative for your long weekend in San Juan: There is an amazing lagoon in the heart of Condado (Laguna del Condado) that separates Miramar and Condado neighborhoods, also very close to Ocean Park. There you can rent paddle boards or kayaks and go around it for an hour or so.  There are manatees, starfish, turtles, and many other animals in the water. Really cool experience!

3 Days in San Juan Puerto Rico Itinerary Summary
Itinerary Summary – Pin me for later!

Day two – Day trip to El Yunque & Luquillo Beach + night out in San Juan

El Yunque & Luquillo Beach: I highly recommend going to El Yunque if you have a long weekend in San Juan. It is the only tropical rainforest in the contiguous U.S., only 40 minutes from the city. The forest offers breathtaking mountain views, lots of hiking trails, a nice river and several waterfalls. You can rent a car and drive yourself or join a guided tour. El Yunque can be an all day thing or you can combine it with Luquillo Beach like we did. 

I wrote an entire blog post about a day trip to El Yunque. You can read all the details here. It really is the perfect day trip. The best part? You can be back to San Juan just in time for dinner and a fun night out.

Mountain View in San Juan
One of the many overlooks at El Yunque

Night out in San Juan

During our second and last night in San Juan we joined some friends and pretty much just walked around the streets. We went back to visit La Fortaleza street at night and stopped at several popular bars. 

We started our night in one of the most popular spots to hang out on a Saturday night: La Placita de Santaella. There are lots of bars, lots of restaurants and people out dancing in this area. I will be completely honest with you, I did not like the vibe there. We felt like there was too much going on, and most people were just there to get wasted. I figure the rain also affected our experience, since the crowds were all looking for a roof to shelter. Perhaps if you visit early on a calmer day there will be a better atmosphere.

From there we went back to Old San Juan, and visited a few bars. Old San Juan is alive on Saturday night, and the area has a great and fun vibe at night.

La Factoria is the Despacito bar! It’s one of the most popular bars in San Juan. It’s even on the list of the World’s 50 Best Bars. There are 7 different rooms, and each one plays a different style of music. Very unique but also very crowded and noisy. There was even a line at the door! Pass by for a selfie and a drink, but definitely not the place for an entire night out. 

Outside of La Factoria Bar, where they filmed Despacito
Outside of La Factoria Bar, where they filmed Despacito

Our favorite bar was La Verguenza Bar. This place has three stories with a rooftop terrace on the third floor, live music, great mojitos, wonderful water views and fun atmosphere. You won’t see the water if you come at night, but you can still breath in the fresh air. From there you can also see La Perla. Also, bring a dollar bill, there are tons of them signed & taped to the walls!

Day three – Bacardi Rum Factory + Calle Cerra + Afternoon at Condado Beach

On day three of our long weekend in San Juan, we had until 3 PM before heading back to the airport. That seems like a short amount of time, but we managed to do a lot. Details below:

Bacardi Rum Factory: our first stop was the well-known Bacardi Rum Factory. Bacardi is one of the best rums in the world. This tour shows you the process of making the rum and the history behind it. You also get to see some great views of El Morro from the welcome center. The area is very chic and modern. We got some engraved rum bottles as souvenirs which was also cool.

Casa Bacardi - Factory Tour
Casa Barcardí welcome center, you can see El Morro across the bay.

Calle Cerra, Santurce: This area has great street art and a artistic vibe. This is where they have Santurce es Ley every year, a large street festival. We walked around, stopped for some great artisanal donuts at Kudoughs and then tried our first Medalla (Puerto Rico’s beer of choice) at La Esquina Watusi, a typical Puerto Rican Chinchorro (bar). 

La Esquina Watusi, a typical Puerto Rican Chinchorro
Medalla Light is Puerto Rico’s beer of choice

Condado Beach: Last but certainly not least, our last stop was Condado beach. This area reminded me a lot of Miami Beach, very touristic, but fun and with a lively vibe. We walked around and visited the poolside bar at the famous and luxurious Condado Vanderbuilt hotel. It’s a great area to unwind and have a couple of drinks overlooking the ocean. You don’t need to be a guest to go in. Check just in case, that might have changed due to the current global health situation.

Sea view from the Condado Vanderbuilt hotel

Before leaving, we looked for a place to eat and randomly picked Tijuana Bar & Grill, a Mexican restaurant a few blocks from the hotel. The food was surprisingly delicious and the margaritas were strong! From there we had a delicious dessert at Señor Paleta which is also around the block.

Señor Paleta Condado Beach

We had a fantastic time in Puerto Rico and we cannot wait to go back and explore other parts of the island. It reminded us a lot of Havana and our entire island!

I am sure you will love your trip and I hope my itinerary serves as a starting point to plan your upcoming long weekend in San Juan, Puerto Rico.

3 thoughts on “A long weekend in San Juan, Puerto Rico: the perfect itinerary

  1. Loved this post! Obviously I won’t be visiting anywhere outside of Australia any time soon but Puerto Rico sounds like a super interesting place and great itinerary. 🙂

    1. Thank you, Caitlin! Glad you liked it. Puerto Rico is indeed an interesting island, and there is so much more to see. Hope you can make it to this side of the world soon! <3

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