As the capital city of Puerto Rico, San Juan is the tourist epicenter of the island. While most people think of San Juan as just the romanticized Spanish colonial city of Old San Juan, there is a healthy balance of activities, entertainment, and gastronomic options located both within the old city wall and the modern city beyond it.
Whether you’re a cruise visitor for a day or staying for an entire week, here are some of the best things you should do, eat and drink to make the best of your time in San Juan.
All of these tips are coming from a local (me!) who was born and raised in San Juan!
1. Go back in History at the Castillo San Felipe del Morro
Commonly known as El Morro, this 16th-century citadel is one of the most well-known attractions not only in San Juan but also in all of Puerto Rico.
With a strategic location overlooking the entrance to the San Juan Bay, El Morro played a significant role in the defense of the Spanish colonial port city from 1539 to as recent as WWII under American Military Occupation.
This UNESCO World Heritage Site has an entrance fee of $7.00, which also includes a visit to Castillo San Cristobal within 24 hours of purchase.
2. Explore “the Other Fort” in San Juan
Considered as “the other fort” in San Juan, Fort San Cristobal is like El Morro’s younger sister living in the shadows of its older and more famous sibling.
But, San Cristobal should not be missed! It is the largest European fortification in the Americas, and it is host to the infamous Devil’s Guerite (Garita del Diablo). Legend says that soldiers disappeared randomly as they stood watch in this guerite.
While El Morro was designed to protect San Juan from sea invasions, San Cristobal did the same task against land invasions.
Between the defenses at El Morro to the west, the massive wall surrounding the old colonial city, and Fort San Cristobal to the east, Spain made Old San Juan almost impervious to attack from land or sea. The $7.00 entry also includes access to El Morro.
3. Visit the Oldest Cathedral in Puerto Rico
From the outside, the San Juan Bautista cathedral looks quite simple, but for what it lacks in elaborate architecture, it makes up for with its rich history and importance.
As the oldest cathedral in Puerto Rico and the second oldest cathedral in the Americas, San Juan Bautista contains the tomb of Spanish explorer Juan Ponce de León – who famously searched for the fountain of youth.
It also houses the shrine to Carlos Manuel Rodríguez Santiago. He was the first Puerto Rican and the first layperson in the history of the United States to be beatified.
4. Do a Sunset Sail Aboard a Historic Schooner
Want to see Old San Juan from a different angle? Hop aboard The Amazing Grace!
This beautiful seven-sails vessel is an 81 topsail schooner replica of the traditional American sailing crafts. These vessels fought the British in the War of Independence and again in 1812, both times as ships of the U.S. Navy and as privateers.
During this trip, you’ll be able to see the city from the water on the historical San Juan Bay while enjoying a beautiful Caribbean sunset filled with music, delicious appetizers, and breathtaking views of the walled city.
It is recommended to book ahead of time as this is a popular activity in San Juan.
5. Hop on a Mini Boat and be Your own Captain
If you’d like a water adventure on the historic San Juan Harbor, but on a smaller vessel, then a mini boat is perfect for you! These mini boat rides are a unique adventure and perfect for those that want to take control and captain their own boat.
With a maximum capacity of up to 4 people, this is perfect for families and couples alike.
During the ride, you’ll explore San Juan’s captivating landscapes and stop a few times to learn the highlights of the city’s history. The thrill of operating your own powerboat while riding and sightseeing across the San Juan Bay is incomparable.
6. Take a Selfie at La Puerta de la Bandera
Since 2012, the entry doors of this dilapidated building on San José Street have become a symbol for most Puerto Ricans living under the current economic crisis the island is facing.
The artist, Rosenda Álvarez, originally painted the doors with the Puerto Rican flag, only to revisit her mural four years later by muting the red and blue of the flag and painting them black.
It was her criticism of the controversial newly-imposed fiscal oversight board that controls the island finances. These doors are now a popular selfie spot among tourists and locals.
7. Feed Pigeons at Parque de las Palomas (Pigeon Park)
If you’re okay with being close to pigeons, then I recommend visiting this small park at the edge of the fortification walls in Old San Juan – just at the end of Calle del Cristo.
As the name says, the park is plagued by hundreds of pigeons waiting to get fed with corn and bird food, which you can buy from a local seller for $1.
Contrary to typical pigeon behavior, these pigeons are so used to humans that they will fly to you and stand on your head, arms, and shoulders as you feed them.
This park is a popular spot among locals, especially families with small children. I fed lots of pigeons here when I was a kid!
It may be a small park, but it is a calm space away from the hustle and bustle of the city.
8. Pray for a Miracle at The Capilla del Cristo
Renowned for its healing powers, this small chapel was built in 1753 at the edge of the stone wall cliff where a miracle supposedly happened. Since then, thousands of faithful Puerto Ricans come every week to pray for their own miracle.
The folk story goes that in 1753, a rider in the San Juan Bautista celebrations traditional horse race lost control of his horse and plunged to the cliffs below.
The then Spanish Secretary of Government, Don Mateo Pratts, watched the event unfold as he supposedly cried out, “Christ of Good Health, save him!” Supposedly, thanks to his cry, the rider survived, but the horse didn’t.
If you want to go into the chapel, it is only open during Saturdays and Sundays.
9. Visit La Perla to Dance to the Beat of Despacito
As a shanty town originally established in the 19th century to house former slaves and homeless non-white servants who weren’t allowed to live within the city walls, La Perla has dealt with centuries of bad reputation.
But that has slowly changed in the past few decades, even more so now with its new-found fame as the location where Luis Fonsi’s Despacito music video was filmed. The neighborhood was badly damaged during Hurricane Maria, but it is slowly rebuilding.
If you visit on a Sunday night, go partying at La 39 Bar, an open-air makeshift bar built on the roof of a house that got partially destroyed during the hurricane.
Don’t forget to drink a Medalla beer, the most popular Puerto Rican beer we all love.
10. Search for Prominent Locals at a Historic Cemetery
The Santa Maria Magdalena de Pazzis Cemetery is a colonial-era cemetery where many of Puerto Rico’s most prominent residents rest in peace.
Even though it is located right in between El Morro and La Perla, it is often overlooked by tourists, as it lies just outside the wall, facing the sea.
Some of the most famous names found in this cemetery are Pedro Albizu Campos, José de Diego, and Jose Celso Barbosa, among many others.
11. Kayak in the Condado Lagoon at Night
Puerto Rico is well known for its stunningly bright bio bays, but all of them are relatively far from San Juan. Now, this shouldn’t stop us from being creative, right?
You can now kayak and stand-up paddleboard (SUP) in the Condado Lagoon at night with glowing kayaks and SUP.
This award-winning LED Night Paddle “City Lights / G L O W” excursion is unlike anything you’ve done before!
You’ll paddle around the lagoon, underneath the lagoon’s historic bridge, and under the stars, while enjoying the LED glow of your Kayak (or SUP) as well as the city lights surrounding the Condado Lagoon.
If that’s not enough, your kayak or SUP has a clear bottom, giving you a “window into the lagoon!” You may have the chance to view marine life such as tiny baitfish (think of Finding Nemo), lobsters, giant orange starfish, stingrays, and more.
This is another excellent way to see the city from a different perspective and have an absolute blast while doing so.
12. Debate on Who Invented the Piña Colada – Puerto Rico’s National Drink
One of the most interesting fun facts about Puerto Rico is that the Piña Colada was invented here!
Folk stories tell us the piña colada was invented back in the early 19th century when Puerto Rican pirate Roberto Cofresí offered his crew a cocktail made with pineapple, coconuts, and rum to boost their morale. But then, with his death in 1825, the recipe for the piña colada was lost.
It took over 125 years for the world to taste this delicious drink again. The “official” piña colada we know today was invented in 1954 by Ramón “Monchito” Marrero while working as a bartender at the Caribe Hilton. He settled on a recipe he said captured the true nature and essence of Puerto Rico.
On the other hand, Barrachina, a famous restaurant in Old San Juan, also claims that their bartender, Don Ramon Portas Mingot, invented this popular drink in 1963.
Even though the hotel got the governor’s recognition of their claim in 2004 to commemorate the drink’s 50th anniversary, both locales still argue on who’s the real inventor.
This is a never-ending argument, so why not try them both and decide which one is the most delicious, at least?
13. Delight in Everything Chocolate
Even though Chocolate Cortés was founded in the Dominican Republic in 1929, it has been a favorite chocolate brand among Puerto Ricans, especially when used as hot chocolate or for dessert.
Now, they have a restaurant and bakery, Chocobar Cortés, where you can try delicious appetizers, main entrees, and of course, desserts, all made with their famous chocolate. Prices range from $3.50 to $22.00 per plate.
14. Relax at the Beach
You can’t visit Puerto Rico and not got the beach!
While the island has some of the most stunning beaches outside of San Juan (think of Vieques and Culebra islands!), you can still enjoy a lovely day at the beach at some of the most popular beaches in the capital city.
Among the best beaches in the city are Hobbie Beach, Pine Grove Beach and Condado Beach, and Ocean Park Beach.
While the small town of Rincón is Puerto Rico’s surfing capital, you can still surf some smaller waves at Pine Grove Beach.
15. Dance and get Buzzed at La Placita de Santurce
Known as La Placita by locals, or The Little Market, this is the most popular hangout spot for locals during the weekend, especially Friday and Saturday nights (but mostly Friday).
La Placita is not just one place, but a conglomerate of businesses in one spot.
The “real” La Placita de Santurce is actually a colonial-style produce market during the day, but after it closes in the afternoon, the restaurants and bars surrounding it come to life until the early morning hours.
Here you can find everything from salsa dance floors, reggaetón music clubs, to LGBT bars, and even upscale restaurants, all in one place.
But, the best thing about La Placita is that even though it’s made of several businesses, the crowd mixes on the street and hops between different locales based on their mood.
If you get there early enough for dinner, you can visit Santaella, a popular upscale restaurant by chef Jose Santaella. Making a reservation beforehand is recommended, given that it is a popular restaurant.
16. Go Shopping at Plaza Las Americas Mall
If shopping is your thing, then you must head to Plaza Las Americas, the largest shopping mall in the Caribbean and the second largest in all of Latin America.
With over 300 stores and “the center of it all” as its slogan, Plaza Las Americas does have it all, ranging from high-end stores to local art crafts, tech stores, and plenty of restaurants and fast foods.
17. Get those Miami Vibes along Ashford Avenue in Condado
Ashford Avenue feels like an even more Caribbean version of Miami Beach with its Miami-style architecture, its high-end stores, beachfront cafes, and trendy hotels.
Walk along the avenue to soak in its vibrant atmosphere. Take some breaks here and there to admire the view of the beach from the Ventana al Mar park, Parque del Indio (Indian Park), Playita del Condado, or from any of the narrow streets leading to the beach.
This avenue is also lined with dozens of hotels, so everything around here is very tourist-friendly.
Also worth checking out is the Fortin San Gerónimo de Boquerón, which can be seen from Playita del Condado (Condado’s Tiny Beach), all the way to the west end of the avenue – by the bridge.
During late afternoons and nights, have a drink and snacks at the outdoor Surf Caffe (one of my favorite spots here), have a vibrant night at the historic La Concha Resort, and listen to live bands at the Hard Rock Café. There are so many hangout spots in Condado to list here!
18. Go to a Speakeasy-like Bar
It’s easy to miss La Factoria if you don’t know about it or are not looking for it. Yet, this place is so famous among locals that it doesn’t need a sign outside.
La Factoria is located where the popular Hijos de Borinquen bar used to be (you can still see its name inside, painted on the wall), and they still kept its iconic low-key vibe.
But, once you pass through the hidden back door, you’ll discover that La Factoria has a lot more to offer. Beyond it are four more individual spaces in sequence, including a wine-bar, dance floor, and cellar-like bar, each with its own music, vibe, environment, drinks, and food.
I really love La Factoria!
19. Eat a Delicious Tripleta
There’s no shortage of delicious street food in Puerto Rico, especially now that the food-truck craze has taken over the island. Now, even though the food truck craze is new-ish, Puerto Rico has had its own traditional food-truck dish for decades. I present to you, the Tripleta.
What’s a Tripleta? It’s a sandwich. But such a yummy sandwich!
Tripleta sort of means “triple,” so this sandwich has marinated grilled cube steak, chicken, and ham or pork. It is served on a soft loaf of sweet potato bread with chips, ketchup, and mayonnaise.
Trust me; it is delicious! Especially when you have those post-drinking munchies. Oh, yeah, these food trucks are often open until really late.
There are dozens of tripleta food trucks all over the city, but among the most popular tripleta trucks is El Churry, found in Isla Verde and many other locales.
20. Take a Peek at La Fortaleza
You will not be able to enter La Fortaleza since it’s the Governor’s home and office, but you’ll be able to see it from its gate.
The building’s Spanish colonial architecture has always been impressive, but in recent years, the former First Lady took the initiative to decorate the street leading towards the main gate, Fortaleza Street. This initiative has been kept, with decorations changing every other season.
21. Have a Gastronomic Experience at Lote 23
Lote 23 is a modernized city version of the traditional beachside kiosks commonly found in Puerto Rico. Each kiosk offers varied and experimental food, in an open environment with live music or, if it’s a game night, a giant screen to watch the match.
They also have tons of activities during the day for kids and families, and a local crafts market.
There you’ll find experimental criollo dishes, burgers, “asianrican” dishes, cocktails, and craft beers, among many others.
22. Cool Down with a Piragua
Whether it’s a hot day or not, if you spot a small cart with the word “piraguas” written on it, stop there and buy one.
Piraguas are traditional crushed ice cones flavored with local fruit syrups like strawberry, cherry, passion fruit, tamarind, lemon, coconut, and many others.
Piraguas are now a dying tradition, but you can still find them in Old San Juan, especially near El Morro and Paseo la Princesa.
23. Have the Most Filling and Delicious Breakfast at Bistro Cafe
Bistro Café is one of the best breakfast/brunch places in all of San Juan. Located in Isla Verde, this café is known for its big plates and a wide selection of creative pancakes, waffles, omelets, and more. Everything is so good!
It gets very crowded, especially during the weekends, so its best to go early in the morning. This place is popular and can have a queue/waitlist.
My favorite plate is The Frida. Sooooo yummy!
24. Visit a Local Brewery
Puerto Rico has had its popular Medalla Light beer for decades now, but now there’s a surge in local craft beers and breweries on the island. Among my favorite new local beers is Ocean Lab Brewing Co.
As their slogan says, this beer is “born on the beach” right at the Vivo Beach Club in Isla Verde.
While you can find Ocean Lab beers in many bars across the island, there’s nothing like tasting it in its birthplace. Ocean Lab also offers tours to their brewery every other Saturday for $10. Check their calendar here to book your spot.
This is a great alternative to the famous Bacardi Rum Factory Tour, which you can also do from San Juan.
25. Go Bar Hopping along Calle Loiza
Calle Loiza has had a mind-blowing transformation in the last ten years, going from a worn-down street with a rough reputation to a popular hanging area with some of the best bars in San Juan.
Dance salsa to the beat of a live band at Piso Viejo, relax with some drinks at Tántalo, feel like you’re in a barbershop at El Bar Bero, or just chill outdoors with a cocktail at Tresbé, a cute and casual bar and restaurant on a shipping container.
There’s so much more to do in San Juan, but just here, you have plenty of activities to keep you busy for a week!