The sun-kissed Caribbean island of Puerto Rico is a U.S. territory with a melding of Latin and Caribbean ambiance. It ranks #2 on my list of the 20 Best Caribbean Islands. Established in 1521, the old walled section of the city is the oldest city in the US (a little older than St. Augustine, FL) and is the highlight. Things you must see in Old San Juan (Viejo San Juan) include ancient forts that once protected the city and colorful cobblestone streets. The frozen-in-time atmosphere makes it one of the most enchanting destinations in the Caribbean.
Best Time to Visit San Juan
- January – March – hot and sunny but less humid and wet, with an average temperature of around 80 to 82°F.
- April and May – although there is more rain as hurricane season approaches, it is quieter and cheaper.
- June to November – hurricane season.
- December – peak season due to Christmas and New Year’s with prices much higher as a result.
Here are 20 places you must see in Old San Juan.
1 Wander the Colorful Streets
Old San Juan is a photographer’s dream, so my favorite must see in Old San Juan is simply strolling around the colorful streets. It’s like entering a time capsule filled with pastel-hued Spanish colonial architecture, massive historic forts, charming plazas, and cobblestone streets around every corner.
2 Castillo San Felipe del Morro
This 16th-century UNESCO-listed fort is the ultimate place you must see in Old San Juan. Perched on an islet overlooking the Atlantic Ocean, “El Morro” has been an important outpost for Spain and then the United States.
Its ramparts protected San Juan from pirate attack and British and Dutch invaders when it was ruled by the Spanish, then later served as a U.S. military installation during WWI and WWII. The massive site includes tunnels, ramparts, and antique cannons.
3 Castillo San Cristobal
El Morro’s sister fort, San Cristobal is also one of the biggest fortresses in the Americas. Located on the opposite side of Old San Juan from El Morro, construction began in 1634 and took 150 years to complete. It houses the Garita del Diablo, a sentry box where a soldier is believed to have been kidnapped. The fort also offers magnificent panoramic views of the city.
You can easily get to the El Morro fort from Castillo San Cristobal. With no stops, the walk between the two forts is approximately 20 minutes. Starting at San Cristobal, walk on Calle Norzagaray along the sidewalk passing by the entrance to La Perla neighborhood, finally ending up on the lawn of El Morro.
4 Calle Forteliza
Jorge Rodriguez, CC BY 2.0 via Wikimedia Commons
Extending eastward from the Governor’s Mansion – one of the Spanish settlement’s defensive structures – is Calle Fortaleza, aka “Umbrella Street.” This is one of Old San Juan’s oldest and most photogenic streets. This is where you’ll find Barrachina (#8 below), which is considered by many as the birthplace of the piña colada.
5 Playa Capitolio
Playa Capitolio (aka Playa Bajamar) is a little-known secret of the locals. It is not the most beautiful, largest, cleanest, or safest beach, but it is the only beach in Old San Juan.
The main “entrance” is across the street from El Capitolio where we discovered steps that lead down to the beach. There is no sign by the steps indicating that there is even a beach there and if you don’t know where to look, you’ll likely not find it.
Be aware that the rough waves and strong rip currents make it not very safe to swim, but it’s a nice place to take a refreshing break.
6 Cuban Burger
If you are a carnivore like me, this fusion of the iconic American hamburger and traditional Cuban sandwich just doesn’t get any better than this! My concoction from the Green Parrot, consisted of a thick burger topped with pulled pork, sliced ham, bacon, and other accoutrements, piled so high I could not take a proper bite. But I was tenacious and finished the whole delicious thing!
7 Plaza de Armas
View from my boutique hotel balcony
San Juan’s charming main plaza is surrounded by colonial government buildings, and a must see in Old San Juan if you want to immerse yourself in the island’s Spanish-Caribbean historical atmosphere. Grab a cup of the legendary coffee (#10 below), some ice cream, or a pastry and relax, or people-watch if that’s your thing.
8 Barrachina
Did you know the piña colada is the national drink of Puerto Rico? I could not resist a memorable visit to Barrachina, which claims to be the exact place where the delicious cocktail blend of coconut cream, pineapple juice, and rum was invented.
9 La Perla
Puerto Rico’s most infamous shantytown, La Perla (the Pearl) was established in the 18th century. Initially, the area was the site of a slaughterhouse called El Matadero because it was built by slaves and homeless servants who were required to live outside the city walls. Nowadays, brightly painted houses and murals take advantage of La Perla’s unique vantage point overlooking the Atlantic Ocean.
La Perla has been the setting of various music videos, including “Despacito” by Luis Fonsi and Daddy Yankee. This picturesque village has a few bars and is becoming a hangout for visitors seeking a unique experience. Community leaders hope tourism can contribute to the growth and development. La Perla is open to visitors who enter their community with respect.
10 Puerto Rican Coffee
I am a coffee aficionado, so naturally trying legendary Puerto Rican coffee was high on my list. The tropical climate, fertile soil, and altitude where the Arabica beans are grown make Puerto Rican coffee special, giving it a rich and supple body with sweet and fruity nuances, with subtle hints of chocolate in the aftertaste.
11 Santa Maria Magdalena de Pazzis Cemetery
Located a short walk from the El Morro fort, San Juan’s seaside cemetery is another incredible thing to do in Puerto Rico. Located on the water, just outside of the walled city, this stunning colonial-era cemetery dates back to 1893. While some tombs were damaged from the hurricane, locals have taken it upon themselves to clean up and restore them.
12 Capitol
This grand Neoclassical Revival building sits just outside the wall into the Old San Juan area. Designed by Rafael Camoega, it was inaugurated in 1929 and was the former residence of Commissioner Luis Muñoz Rivera. The dome in the middle of the building wasn’t built until 1961. Inside are murals and mosaics depicting Puerto Rico’s history.
13 La Rogativa
La Rogativa (the procession) is a famous bronze statue located in the Plazuela de la Rogativa. The monument commemorates one of the most epic legends of Puerto Rico. When the British attacked Old San Juan in 1797, a quick-thinking priest led the outnumbered soldiers and civilians on a religious procession through the city. They fooled the British who abandoned their attack.
14 Dona Fela
Felisa Rincón de Gautier, known affectionately as Doña Felisa or Doña Fela, was the first woman mayor of San Juan and one of the most prominent political figures in the history of Puerto Rico. She became an activist in the suffragist movement and was the 5th woman to register to vote when the right was granted to Puerto Rico in 1932.
The Felisa Rincón de Gautier Museum in the heart of Old San Juan is the mansion where she lived for two years after she was Mayor of San Juan and has become a public museum dedicated to displaying her life and good works.
Click here to read Dona Fela: Puerto Rico’s Most Impressive Woman.
15 Catedral de San Juan Bautista
This second-oldest cathedral in the Americas is one of the finest in all of Puerto Rico. Built in 1521, the Metropolitan Cathedral Basilica of Saint John the Baptist may not look like much on the outside, but the inside is filled with spectacular windows and artwork. You can also visit the remains of the legendary conquistador Ponce de Leon (who famously hunted for the fountain of youth in Florida) buried inside.
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16 El Yunque National Forest
Just a short drive from San Juan, El Yunque National Forest is the only tropical rainforest in the U.S. National Forest System. Considered sacred by Puerto Rico’s communities, there are so many things to do in El Yunque Rainforest, such as hiking trails, waterfalls, wildlife, and the epic Yokahu Observation Tower which offers stunning views.
17 Condado Beach
Just a short drive from Old San Juan, Condado Beach, in one of the more upscale neighborhoods, is over a mile long, lined with restaurants, boutique shops, and high-rise hotels.
The popular golden sands and turquoise waters are perfect, but take care because the undertow here can be deadly.
18 Cueva Ventena
Cueva Ventana translates into “window cave.” The hike to the mouth of the cave takes about 15 minutes, partly uphill, and can be slippery. The cave contains stalagmites, stalactites, petroglyphs, and bats. Unfortunately, the cave was recently shut down for failing to operate with proper permits. Please check for re-opening before going.
19 Bioluminescent Bay
Bioluminescent bays are bodies of water where microscopic organisms called dinoflagellates grow in quantities large enough to produce a “glow-in-the-dark” effect called bioluminescence. When you disturb the water, these organisms glow in a neon blue-green color, making the water look as if it was lit by billions of tiny stars. Laguna Grande in Fajardo, about an hour away from San Juan, is one of three places in Puerto Rico where you can kayak to witness this phenomenon.
20 Lechon Asado
About an hour from San Juan, the mountain town of Cayey receives droves of locals and tourists to an area known as Guavate. Drive along Route 184 (aka La Ruta de Lechon) up the mountain where you’ll find lechonera after lechonera serving slow-roasted whole pork. Lechón asado was declared a Puerto Rican gastronomic heritage.
Conclusion
Old San Juan is one of the best old towns in the Caribbean. From the historic forts standing sentry over the city to tropical beaches and delicious food, there’s something for everyone. Old San Juan is a fascinating fusion of culture, history, and natural beauty that will leave you wanting to return.
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About the Author
Patti Morrow
is a freelance travel writer and founder of the award-winning international blog Luggage and Lipstick and the southern travel blog Gone to Carolinas. TripAdvisor called her one of the “20 Baby Boomer Travel Bloggers Having More Fun Than Millennials” and she was named one of the “Top 35 Travel Blogs” in the world.
She is also the star of the upcoming TV series “Destination Takeover” which is scheduled to premiere in the next few months.
Patti is the author of the book “Girls Go Solo: Tips for Women Traveling Alone,” and has over 150 bylines in 40 print and online publications, including The Huffington Post, International Living Magazine, Washington Post Sunday Travel, Travel Girl, Travel Play Live Magazine, and Ladies Home Journal. She has traveled extensively through six continents looking for fabulous destinations, exotic beaches, and adventure activities for her Baby Boomer tribe.
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