Whether you’re visiting San Juan on a cruise or spending a few days in Puerto Rico, an Old San Juan walking tour should be at the top of your list of things to do!
As a former cruise ship worker, San Juan was one of my favorite ports to explore week after week.
One of the best decisions I ever made was taking myself on a self-guided walking tour of Viejo San Juan.
In just 3-4 hours, I was able to hit all of the major historical landmarks and popular photo-ops/ Instagram hotspots– and so can you!
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Self-Guided Walking Tour Suggested Routes
A self-guided tour through Old San Juan can be broken down into two main sections:
- The coastal perimeter (marked in black on the map)- Where most of the historical landmarks are located
- The interior streets (marked in burgundy on the map)- Where most of the photo spots, restaurants, and shops are found
If you want to hit all the locations listed on this free Old San Juan walking tour, I recommend breaking down your route into the two sections like I did and doing one after the other (in any order).
For those arriving from the cruise ship port, it may make more sense to walk around the exterior first and then end the day perusing the downtown streets.
I began this tour in the interior section as I took an Uber to Plaza Colon. After walking all the way down to the Umbrella Street, I then made my way clockwise to the listed destinations.
The Coastal Perimeter
Paseo de la Princesa
Paseo de la Princesa is a beautiful promenade lined with fountains, lamp posts, and trees— all accompanied with stunning views of the San Juan Bay.
On this picturesque boardwalk, you’ll find street vendors, art exhibits and shops, restaurants, bars, and even live music.
Address: 54 C. de la Fortaleza, San Juan
Where to stay in Old San Juan: Old San Juan Guest House, El Colonial Adults Only, Casa Sol Bed and Breakfast, Fortel Hostel
La Fortaleza
National Historic Landmark La Fortaleza (The Fortress) was built in the mid-1500s for military defense.
Since its establishment, it has served a number of purposes in addition to a fortress, including a prison, arsenal, and its current function as the governor’s residence.
Because the building is still an active government building, those interested in looking inside can only do so through official guided tours. These 30-minute tours are offered throughout the weekdays.
La Fortaleza can be seen from a distance while on the Paseo de La Princesa as well as at the end of the Umbrella Street (Calle Fortaleza).
Address: 63 C. de la Fortaleza, San Juan
Puerta de San Juan
Puerta de San Juan is the city’s iconic colorful gate that’s found at the northern end of Paseo de la Princesa.
It’s a historical landmark that was previously used to protect the city during colonial times.
Standing 16 feet tall, the gate is also inscribed with the phrase, “Benedictus Oui Venit In Nomine Domini,” which means, “Welcome those who come in the name of God.”
Address: Cll Caleta De San Juan, San Juan
Museo de las Americas (Museum of the Americas)
The Museo de las Americas promotes the history and culture of the Americas through permanent and seasonal exhibits.
Visitors can learn about the indigenous, African, and European influences that shaped the Americas into the multi-faceted countries that they are today due to colonization and modern development.
The museum is actually inside what used to be the military’s barracks (Cuartel de Ballajá) during the colonial period. The beautiful courtyard is definitely a sight to take in!
You can also find unique, local folk art during the museum’s Domingo de Artesanos, which is an art showcase on the first Sunday of every month.
Address: Calle Beneficencia, San Juan
Website: museolasamericas.org
Hours: Thursday- Sunday 11 a.m.- 4 p.m.
Price: General Admission- $6; Under 12 and over 65 years old- $4
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Castillo San Felipe del Morro (“El Morro”)
Castillo San Felipe del Morro (also known as “El Morro” for short) is the island’s trademark fortification built at the tip of the San Juan Bay.
Completed in 1790, the six-level fortress was strapped with a cannon, and together with another yet smaller fort, Fortín San Juan de la Cruz (“El Cañuelo”), the two structures produced a crossfire that would protect the bay’s entrance from intruders.
There’s so much to explore inside the fortress, from barracks and batteries to panoramic views of the bay.
El Morro’s presence domineers over everything in nearby site.
The vast green lawn that leads up to the fort’s entrance is the perfect location for a picnic, sunbathing session, or just a short break during your walking tour.
Although there are always groups of people hanging out, the area is so spread out that you’ll have no problem finding space for yourself away from others.
Tip: Keep your receipt! El Morro and Castillo San Cristóbal only require one entrance fee for both locations, so you’ll be able to get a 2-for-1 deal as long as your receipt shows that you’ve already paid for one ticket.
Address: Calle del Morro & Calle Norzagaray
Hours: Daily 9 a.m.- 6 p.m.
Price: General Admission- $7; Free for children under 15
Cementerio Santa Maria Magdalena de Pazzi
Just outside El Morro you’ll find the Santa María Magdalena de Pazzis Cemetery.
While it may seem strange that a cemetery is a landmark, the beautiful graveyard overlooking the Atlantic Ocean is definitely with a visit.
The cemetery’s location by the water was chosen as a way to symbolize a person’s spirit crossing over to the afterlife.
To this day, many of Puerto Rico’s most prominent citizens are laid to rest here.
If you don’t feel like going down and walking through the cemetery, it can easily be admired from the path leading to/from El Morro.
Address: Calle Cementerio, San Juan
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La Perla
Next to Cementario Santa Maria Magdalena de Pazzi and alongside the coast is La Perla, a historical shantytown.
The colorful neighborhood is most widely known recently as the filming location for the 2017 worldwide chart-topper “Despacito” by Puerto Rican artists Luis Fonsi and Daddy Yankee.
La Perla was first established as the location of a slaughterhouse as both slaughterhouses, cemeteries, and homes of former slaves and non-white servants were required to be outside of the main city center in the late 19th century.
Address: Calle Tiburcio Reyes + Calle Lucila Silva + Calle San Miguel + Calle Bajada Matadero
Castillo de San Cristóbal
Castillo de San Cristóbal is El Morro’s sister fortress that was build to protect the city from land attacks.
It’s the largest Spanish-built fortification built in the New World, spanning roughly 27 acres.
The fortress features several sentry boxes (garitas) which are strategic lookout points that guards would use to keep an eye out for any potential threats.
Visitors can explore the different levels of the fortification as well as get a breathtaking panoramic view of Old San Juan and the bay.
Address: Calle Norzagaray & Route 25R (Avenida Luis Muñoz Rivera)
The Interior Streets
Plaza Colón
Plaza Colón is the land entrance to Old San Juan and can be recognized by its monument dedicated to Christopher Columbus.
The plaza is a good meeting or drop-off point if you’re taking a taxi or Uber to/from Viejo San Juan.
Address: C. de la Fortaleza & C. de O’Donnell
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Plaza de Armas
Plaza de Armas is one of the city’s main plazas.
On the northern end lies San Juan City Hall, and on the west is the Department of State building.
At this plaza, you’ll find several statues, a fountain, benches, and street vendors selling local pastries and coffee.
Address: C. de San Francisco & Calle San José
Umbrella Street (Calle de la Fortaleza)
Perhaps one of the most Instagrammable locations in Old San Juan, Puerto Rico, Fortzaleza Street is home to the iconic and colorful hanging umbrellas.
The popular attraction is located at the end of Calle de la Fortaleza, just in front of La Fortaleza, where the governor resides.
It’s worth noting that the hanging decor changes periodically, so you might not always see vibrant umbrellas.
During one of my visits, the umbrellas were all camouflage patterned to represent the military.
In 2021, the umbrellas were replaced by a large banner with the Puerto Rican flag’s design.
Address: C. de Fortaleza, San Juan
Hotel El Convento
Hotel El Convento is a chic 4-star hotel with a rooftop pool that’s conveniently located in the middle of the city.
But more importantly, the few blocks around the area are absolutely gorgeous and worth checking out if you want some colorful pictures!
Address: 100 C. del Cristo, San Juan
Catedral Basilica Menor de San Juan Bautista
One block away from Hotel El Convento is the America’s second oldest cathedral, Catedral Basílica Metropolitana de San Juan Bautista, also known in English as the Metropolitan Cathedral Basilica of Saint John the Baptist.
Built in the mid 1500s, the cathedral is where the body of Ponce de Leon is entombed.
Address: 151 C. del Cristo, San Juan
La Puerta de la Bandera- Puerto Rican Flag Door
Any visitor will quickly see that Old San Juan is an oasis of art, from brightly painted buildings to beautiful murals on doors.
Another iconic photo spot in Puerto Rico is the Flag Door, or La Puerta de la Bandera from local artist Rosenda Álvarez.
Located at 51 Calle San José, a mural of the Puerto Rican flag is painted on the door of an abandoned historical building.
Address: 51 Calle San José, San Juan
Callejon de la Puerta Bandera- Flag Door Alley
Yet another popular Instagram photo location is also of the Puerto Rican flag on a door, but this time in an alley at the end of Calle Imperial.
I stumbled upon this mural without prior research as I was so immersed in the beautiful rainbow buildings in the neighboring streets.
If you have time (and enough energy), I definitely recommend spending a good half hour wandering through the area.
The streets are so colorful and perfect for photo ops.
You could even hire a Puerto Rico photographer for a fun and memorable photoshoot!
Address: Calle Imperial, San Juan
Where to Eat
A favorite restaurant among us cruise ship crew members is the Stuffed Avocado Shop.
While it’s not traditional or local eats by any means, it is the perfect option if you’re looking for a healthy meal with lots of fresh ingredients and greens– especially if you’re visiting San Juan on a cruise!
At this build-your-own-bowl eatery, patrons can choose from a wide and delicious selection of bases, protein, sauces, and toppings.
The menu also has a few “Signature Avocados,” with combinations already made for those unsure of what ingredients to put together.
From cauliflower rice and baby greens to pulled pork and mango tuna, the Stuffed Avocado is both tasty and healthy.
Address: 209 C. de San Francisco, San Juan
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