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Are you planning a trip to the island of Puerto Rico? Although this lush, hilly expanse is technically a US territory, for about 400 years it was controlled by Spain, as evidenced by an abundance of remaining colonial architecture. If you only have a short time in the region, this itinerary will show you the best of the colorful streets of Old San Juan in just one day.
Americans will find in Puerto Rico a large cultural bang for their buck – with no passport required! From art to architecture to arroz con pollo, there is a mixture of influences from the Spanish, West Africans, and the indigenous Taino. In fact, Puerto Rico was my first exposure to Latin America and the perfect chance to practice my Spanish in this largely bilingual country.
With the airport and cruise ship port being located nearby, most visitors focus their time in the compact historical center of Old San Juan. Small as it is, the area is dense with centuries of history, wonderful restaurants, and stylish boutique hotels. This itinerary will show you one perfect day exploring the top sites of Old San Juan.
One Day in Old San Juan Itinerary
If you fly into Puerto Rico, you will arrive at San Juan’s Luis Muñoz Marín International Airport (SJU). From there, you can grab a 20-30 minute (depending on traffic) taxi or Uber into Old San Juan. I have personally found Uber extremely easy and inexpensive to use in Puerto Rico.
For cruisers, there are two main docking areas around San Juan: Pan-American piers and Old San Juan piers. For the latter, you’ll already be right in Old San Juan and can walk to most sites. From the former, you will need to hire a taxi or Uber.
Getting around Old San Juan is easiest on foot, as its small size and traffic congestion make renting a car impractical. Driving is only necessary if you plan to venture beyond the San Juan metro region.
Old San Juan Basics
- Puerto Rico Currency: USD
- Time Zone: Atlantic Standard Time (or one hour ahead of Eastern Time). However, as Puerto Rico does not observe daylight savings time, during much of the year Atlantic Standard and Eastern time are the same.
- Official Language(s): Spanish and English are the official languages of Puerto Rico. Old San Juan is extremely bilingual but outside of main tourist areas you will mostly encounter Spanish speakers.
- Stray Cats: While you will see them everywhere in Old San Juan, I have found that the kitties mostly keep to themselves. The city makes efforts to manage the feline population, but co-existing with them remains a fact of life.
8:00am: Breakfast & Puerto Rican Coffee
The island of Puerto Rico has a coffee growing tradition, so why not try some local brew during your visit? Visit Café Cuatro Sombras for your caffeine needs while also nourishing yourself with some avocado toast or a guava pastry.
9:00am: Tour the Historic Streets of Old San Juan
When I say that old San Juan is dense with history, I mean it. The best way to take in as many of these blue cobblestone streets as possible in one day is to do a guided walking tour like this one. A local expert will reveal hidden history throughout the city that you likely would never have otherwise discovered.
If you prefer to explore at your own pace, be sure to at least include these key sites in your Old San Juan itinerary:
Puerta de San Juan
By the end of the 18th century, Old San Juan was completely encircled by about three miles of stone walls. Five official entrances led into the city, with the Puerta de San Juan (San Juan Gate) being the last that remains today from the Spanish colonial era.
Today, the gate pops bright red against the aged stone wall leading out towards San Juan Bay. Originally, this entrance welcomed the arrival of dignitaries and other important officials. Today, it leads out to the romantic Paseo de la Princesa pedestrian promenade.
This gateway is 16 feet tall and 20 feet thick – the perfect size, I found, to comfortably shelter a dozen or so people waiting out a tropical downpour.
Catedral de San Juan Bautista
An easy two-minute walk from the Puerta de San Juan, the gothic facade of this church will greet you from the edge of Plaza de la Catedral along Calle Cristo. The church is the second oldest in the Western Hemisphere, dating back to 1521.
After the original structure was destroyed by a hurricane, a new one was built in 1540. Over the years, it faced enemy attacks, like that of the Earl of Cumberland in 1598, and centuries of hurricanes and earthquakes. Today, it is the seat of the Archdiocese of Puerto Rico and houses the remains of Juan Ponce de León, or Puerto Rico’s first governor.
I recommend taking a short stroll around the interior of this cathedral to admire its beautiful architecture.
La Fortaleza
This historic structure, officially called El Palacio de Santa Catalina, was built in 1540 as a defensive fortress. Ever since 1846, it has served as a residence for at least 170 governors of Puerto Rico.
The building is open for 30-minute guided tours Monday through Friday from 8:15am to 3:30pm, although last-minute closures happen occasionally. Call ahead to schedule a tour and bring your ID.
Capilla del Santo Cristo de la Salud
Strolling south on Calle Cristo you will eventually run into a small stone chapel called Capilla del Santo Cristo de la Salud (Chapel of the Holy Christ of Health). The structure was built in 1753 when, according to legend, the Secretary of Government Don Tomás Mateo Prats called upon Santo Cristo de la Salud to save a young man who fell off his horse and tumbled over a cliff.
Although it remains unclear whether the young man actually survived, the Secretary of Government ordered the building of a chapel at this spot to honor the miracle. To this day, individuals in need of healing for themselves or loved ones leave silver ornaments at the small altar inside.
11:00am: Visit Fun Photo Spots
Want to take some memorable photos home with you? Don’t miss these popular Old San Juan photo spots:
- Plaza Colón: Pose in front of the “I Love SJ” sign.
- Puerto Rico Flag Mural: This mural on the corrugated metal door of a bright orange building is one of the most recognizable photo spots in the city.
- Calle de O’Donnell: With characteristic blue cobblestones and colorful buildings heading uphill, in my opinion this is one of the most photogenic streets in Old San Juan.
- Call de la Fortaleza: Leading up to the governor’s mansion, this street is decorated with rotating canopies ranging from colorful umbrellas to a giant Puerto Rico flag. Despite being blocked off by police, tourists are still welcome to take photos here.
12:00pm: Break for Lunch
It’s been a busy morning, but the day is not even close to done! However, it’s time to take a pause to re-energize with some lunch. Here are two great suggestions:
- Café Botánico: This cafe serves healthy, yet flavorful bowls and coffee beverages in a garden-inspired space.
- El Mesón Sandwiches: Puerto Rico knows how to do sandwiches, as demonstrated by this popular local chain that has been in business for over 50 years. I recommend the Cuban.
1:00pm: Explore an Old San Juan Fort
The fortifications surrounding Old San Juan are all protected today within San Juan National Historic Site. This UNESCO World Heritage Site includes two main forts that you may have already seen while wandering:
- Castillo San Felipe del Morro (El Morro): The earliest fort in Old San Juan and meant to protect San Juan Bay from sea attacks. Construction started on the fort in 1539 and didn’t end until 1790. The structure has six levels and still contains some of the original cannons facing out towards the sea.
- Castillo San Cristóbal: Built starting in 1634 near the eastern gate of Old San Juan, this fort’s original purpose was to fortify Old San Juan from land attacks. Completed in 1765 and covering over 27 acres, this is the largest fortress built by the Spanish in the Americas.
Entry tickets cost $10 and allow access to both forts within a 24-hour window. Each has great views and beautiful architecture, so it’s up to you whether you wish to visit the oldest fort or the largest one (or both!). Either way, wear a hat and sunblock because there is more sun exposure than you’d think.
2:00pm: Take a Gelato Break
If you get too hot wandering the forts, duck into some a/c at Anita Gelato. You’ll need the time waiting in the long line to make the excruciating choice of which gelato flavors to order.
The selection rotates among over 150 handmade varieties, from tropical fruity combos to dense dark chocolate goodness. Walking around town with this silky smooth gelato is the perfect way to cool off from the Caribbean sun.
3:00pm: Tour One More Fort or Museum
Next, you have two choices: visit one more fort or check out one of Old San Juan’s intriguing museums. Consider whether you’re up for visiting another fort since you already paid for the ticket. Or do you have fort fatigue and don’t mind paying one more entry fee?
If craving the shade of a museum, here are two perfect options close to El Morro:
- Museo Casa Blanca: This home was built in 1521 for Juan Ponce de León (he died before it was finished). Today, this museum houses 16th and 17th century artifacts and has a beautiful garden that is free to visit. Closed Monday and Tuesday, admission is $5.
- Museo de las Américas: Contains contemporary art installations and cultural exhibitions celebrating history and culture in the Americas, with emphasis on Puerto Rico. Exhibitions are housed in historic Spanish barracks. Closed Monday and Tuesday, admission is $6.
4:00pm: Check Out San José Church
Have energy for one more stop? If so, San José Church is easy to visit after either museum or El Morro.
Dating back to 1532, this structure is even older than San Juan Cathedral. In fact, Juan Ponce de León was initially buried here for 350 years. You can even find a statue honoring him outside the church in Plaza de San José.
The church spent two decades closed while undergoing extensive restorations to save it from a state of severe decay. A stroll through the interior will show you a rare Western Hemisphere example of 16th century Spanish Gothic architecture. While the church is generally open from 11am to 5pm (except Monday), hours may vary.
Afterwards, take a short break from sightseeing to get ready for a dinner featuring delicious Puerto Rican cuisine.
6:00pm: Taste Local Mofongo
Old San Juan has a plentiful selection of local restaurants where you can try iconic dishes like mofongo stuffed with your choice of protein and tostones (can never get enough of these). Here are two places to visit for either a casual or slightly more formal vibe:
- Casual: Puerto Criollo for Puerto Rican specialties like mofongo
- Elegant: The Cannon Club Restaurant & Piano Bar, which offers a sophisticated menu and live music.
Want to get a sampling of all the best dishes in Old San Juan in one evening? Do this food tour, which lets you try Puerto Rican coffee, guava pastries, sandwichitos, mofongo, fried pork, tropical fruit popsicles, and even gelato. I did it myself and was beyond full!
8:00pm: Drink a Piña Colada
Did you know that the Piña Colada was invented in Puerto Rico? Ordering one of these tropical libations is the perfect chance to enjoy some nightlife during your Old San Juan itinerary.
- Barrachina: This iconic establishment became the birthplace of the Pina Colada in 1963 (although the Caribe Hilton also makes this claim).
- La Factoría: La Factoría, with its six unique bars each offering different vibes, is one of the most popular spots in town. It was recently chosen as the Best Bar in the Caribbean.
Have 2 Days for Your Old San Juan Itinerary?
If you have two days available for your Old San Juan itinerary, there are plenty more things to possibly see and do around town:
- Pick out another museum to tour
- Check out Casa BacardÍ, the distillery that makes this famous rum
- Take a day trip to the El Yunque Rainforest
- Swim at a nearby beach, like Condado or Ocean Park
- Take a Bomba class
- Paddle through a magical bio bay
- Leave Old San Juan and explore the west side of Puerto Rico
Where to Stay in Old San Juan
Old San Juan is a place where I’d be super reluctant to book an Airbnb unless you can prove it’s owned by a local Puerto Rican resident. Unfortunately, recent years have seen corporate interests buying up heaps of historic homes, thus forcing prices up and squeezing locals out.
The good news is that Old San Juan has some absolutely gorgeous hotels. Here is a selection that I personally have enjoyed:
- CasaBlanca: This is the first hotel I ever stayed at in Old San Juan, and its beautiful tile and rooftop views left me enamored with the city. My reasonably-priced room was comfortable and the staff couldn’t have been friendlier. Plus, I was a short walk from my favorite coffee shop, Cuatro Sombras.
- Caribe Hilton: This oceanfront hotel has a great pool and is where the pina colada (maybe) originated. While not right in Old San Juan, it’s a five-minute Uber and is a great jumping point for dining in other nearby neighborhoods, like Miramar and Condado.
- El Convento: If you like luxury mixed with history, this boutique hotel is perfect. Housed in a 17th century convent, the design features in this space include gorgeous woodwork, tile-backed staircases, and beautiful ached awnings overlooking a courtyard restaurant. The location is superb, overlooking Catedral de San Juan Bautista and being an easy walk from the San Juan Gate and El Morro.
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As you can see, there is no shortage of awesome experiences to include in your Old San Juan itinerary. The opportunity to spend even one day traversing the blue cobblestones of this historic tropical city is incredible! With coastal scenery and colorful buildings all around you, you’ll be enchanted by the vibrant local culture.
