Puerto Rico is one of my favorite travel destinations, and it’s getting all the love after the Bad Bunny halftime show. I get it, and whether you’ve never been or you’ve been going for years, these tips for the best way to spend 48 hours in San Juan is for you.
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Where To Stay In San Juan
Whenever I visit San Juan, I stay in the Isla Verde area. It’s close to the airport, right on a fantastic beach, and just a short ride into Old San Juan.
On my most recent trip, I stayed at the newly opened Aire de Olivo and absolutely loved it. It’s gorgeous, modern, and super convenient.
In the past, I have also stayed at the Embassy Suites nearby with my family and been very happy with the experience. Both are great options that let you enjoy the beach while being close to the action.
Getting around is simple. Within Old San Juan, you do not need a car, as this Chicago girl finds it very walkable. Know that the old town has tons of old cobblestone streets and hills, which can be a challenge if you have mobility issues.
For longer distances or getting between neighborhoods, Ubers and cabs are plentiful and reliable, and we use them to get from Isla Verde to Old San Juan, for example. If you’re heading further afield (can I recommend the bioluminescent bay experience enough? Nope, I cannot), you definitely want to rent a car, and you can do that from the airport or from neighborhood locations near where you stay.
Exploring The Forts
No trip to San Juan is complete without visiting the iconic forts, and this is a perfect way to spend your first day when you have the most energy. You could quite honestly spend the entire day simply focused on the forts.
Both Castillo San Felipe del Morro and Castillo San Cristobal are located in Old San Juan and run by the National Park Service. They are complementary and both worth a visit.
The $10 per person entry fee is valid for both locations. That said, I highly recommend that you get the annual pass, as it’s valid for up to four people at any national park for the next year, including another you’ll want to visit while here.
El Morro
El Morro is a massive 16th-century citadel on the northwestern point of the city and offers incredible views of the ocean. This six-level fort was started in 1539 by the Spanish but not completed until 1787, so you can imagine how large and how many different areas you can explore there.
It’s windy on top, so hold onto your hats and sunglasses (and don’t wear dresses or a skirt like my younger kid did the first time we visited), but definitely trek all the way up. And that wind? It’s perfect for kite flying on the lawn in front of the fort.
To get from the street to the actual fort entrance is an uphill hike. To avoid getting too tired (or hot), plan to use one of the free trams that take you around San Juan. And yes, they are there for anyone to use them.
While you can explore on your own, you also have the option to take a ranger-led tour, and I highly recommend them. My favorite parts? The barracks where soldiers lived and the kitchens that make you grateful for what you have in your home.
Castillo San Cristobal
Just a short 15 minute walk away lies the second major fort in San Juan. San Cristobal, at 27 acres, is actually significantly bigger than El Morro, as it’s the biggest European fortification in North America.
This fort has a steep trek to its entrances (and yes, there are two), as well, but once inside, there are “just” three levels to explore. This fort has a series of tunnels you can explore, and it’s a different experience than El Morro. Definitely take the time to visit both.
Be sure to keep your receipt from your entry to El Morro so you don’t have to pay a second time. It is valid for just one day, so plan well to visit both in the same day or take advantage of an annual pass.
Just like El Morro, there are ranger-led programs throughout the day, so you can get more info than exploring on your own. Each fort is a one to two-hour exploration, depending on how much you want to see and how quickly you go through the areas.
Walk the Streets of Old San Juan
Simply walking around Old San Juan is an activity in itself. The cobblestone streets and colorful buildings are so pretty, and Calle Fortaleza is one of my favorites.
You might know it as the street famous for the pink umbrellas that the territory’s first lady had hung years ago – and yes, I was lucky enough to see the first installation. The installations change regularly now, ranging from kites to flags and everything in between, but it is always colorful and makes for a perfect photo op.
Fortunately for me and possibly for you, the street is right near Barrachina, the restaurant that claims to be the birthplace of the piña colada. This makes it perfect to wander before or after grabbing a meal or a drink, and yes, you can take your drinks to go and explore with them.
As you’re wandering, be sure to stop by the Catedral de San Juan Bautista, the second-oldest church in the Americas and the site where the world’s first archdiocese was founded. It’s a gorgeous old church that you’re free to enter when services aren’t being held.
The Food Scene
Speaking of food, you have to eat your way through this city. Puerto Rico has an incredible food scene that blends traditional criollo cooking with modern fusion trends.
You’ll find mofongo, fresh seafood, and more. There are so many great restaurants that it’s hard to have a bad meal here. I gathered a list of my favorite places to eat in San Juan, so use this as your guide throughout your stay.
Uncover Hidden History with a Walking Tour
One of the more unexpected highlights of my most recent trip was the Women in Puerto Rico History walking tour with Turismo Borincano in Old San Juan. It runs Thursdays through Mondays and takes about two and a half hours.
Discover Puerto Rico booked this for us as part of the press trip, and I was fascinated by all the history I never learned. This tour focuses on the women who shaped the island, and many of their stories are ones that academics are still learning about.
Our knowledgeable tour guide Gloricel shared details on figures like Ana Roqué Géigel de Duprey, a suffragist and educator, and María de las Mercedes Barbudo y Coronado, an independence activist.
We also heard the story of the Cordero sisters, Celestina and Gregorina, who were pioneers in education and others in this small group tour. One side note: this tour involves a lot of walking on those uneven cobblestones and hills, so it might not be suitable for young kids or those with mobility concerns.
Visit Casa-Museo Felisa Rincón De Gautier
On that tour, we visited the Casa-Museo Felisa Rincón de Gautier, but this small museum is worth visiting even if you don’t have time to take the tour. It’s located in the former home of Felisa Rincón de Gautier, the first female mayor of San Juan and a major figure in Puerto Rican politics.
The oldest of eight siblings, she went to New York to learn the fashion trade, eventually opening her own dress shop in San Juan where she made high fashion accessible to local women. She was a trailblazer, one of the first women to vote, and later became a powerful political leader.
Under her administration in the 1950s, San Juan expanded significantly, including the new hotels and the airport. She also championed the preservation of historical buildings, which is a major reason Old San Juan looks the way it does today.
The museum is a beautiful tribute to her life and legacy. It’s open from Tuesdays to Saturdays, and you have to make an appointment in advance to visit, so plan ahead.
I also visited Castillo de San Cristobal, the largest fortification built by the Spanish in the New World. Pro tip: you can buy a discounted ticket that grants you entry to both forts, which saves a bit of money compared to buying individual tickets.
Another stop worth making is Casa Blanca, a museum that was the original governor’s mansion built for Ponce de León. It offers a glimpse into 16th and 17th-century life on the island and has beautiful gardens to explore.
Make Room for Beach Time
After spending a full day exploring all Old San Juan has to offer, spend a day relaxing at Isla Verde Beach. It is one of the best urban beaches in the Caribbean, and both hotels I stayed at have beach chairs and umbrellas they set up for you.
The beach is wide and perfect for building sand castles. Depending on the day and season, the water may be too rough to enter, so watch the flags and lifeguards, but I’ve had pretty good luck being able to enjoy the water, too.
Alambique is part of the Isla Verde Beach that’s closest to the hotels I’ve stayed at, and it’s great for hanging out in the sand. If you Balneario de Carolina is further east and has lifeguards and calmer areas for swimming, but you may need to get a ride share to drop you off, especially as parking tends to fill quickly there.
Don’t Skip El Yunque
So technically, El Yunque isn’t in San Juan, but it’s less than a 45-minute drive from San Juan, pending traffic. You do not want to miss it.
El Yunque National Forest is the only tropical rainforest in the U.S. National Forest system, and it’s absolutely gorgeous. Just remember that the park is capacity-controlled, so you may want to visit earlier in the day so you aren’t disappointed, especially in busy seasons.
With this national park, you can drive through and to a lot of it, and it’s gorgeous just from your car. Stop at the visitor’s center, which does have a fee, and does have a reciprocal agreement for a discount if you purchased an annual pass for the forts.
Whatever you do, make sure you park in designated areas. There are tons of trails with different difficulty ratings, and many of them lead to waterfalls or pools for you to enjoy. This is my favorite part of the park.
You definitely want to pack a swimsuit, towel, and water shoes. The pools tend to be rocky, not the smooth sand beaches you see on the coast.
You can easily spend all day or most of the day at El Yunque. Personally, I like the freedom of renting a car and exploring on my own, but there are so many great excursions that will take you there, too.
Why San Juan Is Always A Good Idea
San Juan always has something going on, and there are things for everyone to enjoy, from history and culture to food and beaches. You won’t have enough time with just 48 hours in San Juan, but it’s a good way to introduce yourself to Puerto Rico and get that next trip booked.