How to Spend a Day in Old San Juan

July 17, 2017

colorful old san juan, puerto rico buildings

Old San Juan owes its charm to the wealth of sights, restaurants, and shops within its 7-block area, and it can be a struggle to prioritize what to see and do in the old town, particularly if your time there is limited. This was exactly the situation my boyfriend Alex and I faced when he and I visited Puerto Rico for 4th of July weekend. With some pre-trip research, I’m proud to say that we planned a stay in Old San Juan perfectly reflective of the old town’s eclectic mix of cultural and historical vibrancy. Here’s how you can do it too.

Before I begin my detailed list of recommendations, I must add the disclaimer that the purpose of this post is not to regurgitate the same list of must-see sights in Old San Juan that any other travel blog or guidebook can and will suggest. I certainly agree that the forts and many of the promenades can’t be missed; in fact, I recapped my own visits to the forts in my last post. However, I hope to offer a different take on the old town from someone who has spent much less time there than desired and nevertheless crafted a unique experience! Most of the recommendations below are doable even for those who are just visiting Old San Juan as a port of call on a cruise; it’s definitely possible to see Old San Juan in a day with careful planning.

colorful old san juan courtyard

In the courtyard just off the apartment we booked through Airbnb.

Before you go

To clarify, Americans can expect Puerto Rico to be a very convenient travel destination since it is, after all, a U.S. territory, meaning that cellular service, currency exchange, customs, and drinking water safety won’t be an issue. Similarly, if you’re renting a car, you can expect the same regard for traffic regulations as in the States, meaning that you should try not to speed, or else you will get pulled over for doing so! If you aren’t planning on renting a vehicle, note that Uber drivers are not permitted to pick up passengers at the airports or at taxi lines (such as those found outside hotels) but are allowed to drop off at these locations as well as anywhere else.

Where to stay

Naturally, you won’t find big chain hotels or resorts in the center of Old San Juan, although there is no shortage of boutique hotels and lodging in the area. Having said this, I highly recommend an Airbnb/VRBO or short-term apartment rental within Old San Juan because this is truly the only way to mimic the experience of someone who lives in the old town. It’ll be more central to shops, restaurants, and sights, thereby cutting down on the need for transportation, which is crucial if your time in the area is limited. Our Airbnb was just across the street from Castillo San Cristobal and a short walk from Plaza de Colon!

What to do

Visit Castillo San Cristobal and Castillo San Felipe del Morro. I know I promised not to repeat well-known destinations within the area, but these historic sites, as well as others, should not be missed simply out of fear of idea that “it’s what tourists do”. If you’re reading this, you are most likely a tourist. It’s an inevitable part of being a traveler and should not be a source of shame!

Take photos on Calle Luna. When we began taking pictures, Alex and I realized that the beauty of the old town’s colorful facades was often marred by crowds or cars driving past, especially on popular shopping streets like Calle del Cristo or Calle San Francisco. However, people just visiting San Juan or rampant vehicle traffic don’t really have any real purpose being on residential streets, where you can be free to take as many uninterrupted shots of the architecture as you’d like. Of course, as in any other neighborhood, be courteous and respect the privacy of residents.

Have a drink or a bite in one of the plazas during the evening. The plazas, while lovely in their own right during the day, take on an entirely different and enchanting vibe at night when street performers and vendors emerge – not to mention the weather is far more agreeable!

Visit the artisan’s shop at Da House Hotel. Interesting name with even more eclectic finds. Here you can peruse an entire floor of soaps, prints, leather goods, and even cigars made by local artisans. I found myself some delightful prints featuring garitas as well as Old San Juan architecture, while Alex found an alarmingly large 12-inch cigar that certainly only be be classified as an impressive gag gift (…right?).

Go on a garita scavenger hunt. I’ve written about my sudden fascination with garitas (sentry boxes) in Old San Juan before, and I’m putting this on the list because I wish I could have done this on my trip. Using this map (which shows the location of every garita in Old San Juan) as a walking guide could provide a great glimpse as to which areas of Old San Juan the Spanish valued the most to the extent that these guard posts existed in those spots.

garita old san juan calle tetuan

Where to eat

deaverdura puerto rican food

The sampler of typical Puerto Rican food at Deaverdura.

Deaverdura. This was the best meal Alex and I had in Old San Juan. The restaurant is casual, small, and intimate, which is to say that it would behoove you to make a reservation by phone if you plan on going for dinner! Deaverdura has no set menu, instead creating dishes made from what has recently been obtained at market. They also offer a sampler platter of typical Puerto Rican cuisine, which includes fried plantains, roasted pork (or lechón), sausage, ham croquettes, and a variety of fritters. We, of course, dove headfirst into this platter. Bonus side note: Their sangria is top-notch.

Punto de Vista. Located on the rooftop of a hotel, this restaurant offers stellar mofongo (a Puerto Rican dish of deep-fried green plantains mashed together or topped with other ingredients such as pork or seafood)  as well as 2 for 1 mojitos in various flavors! Alex opted for the pork mofongo covered with a sweet criolla sauce, while I ordered the same albeit with a creamy garlic drizzle.

criolla mofongo punto de vista

Punto de Vista’s Mofongo with criolla sauce.

Café Berlin. We were elated to have found this cozy bohemian spot just around the corner from our Airbnb. I strongly suggest their signature “Old San Juan Breakfast,” which might not at first seem too groundbreaking with its two eggs, toast, potatoes, and breakfast meat of choice but becomes otherworldly with the addition of the guava butter that comes as a side with the dish.

Señor Paleta. The sizeable line you’ll find upon your approach to Señor Paleta’s small storefront on Calle Tetuan is well worth it. What better way to reward yourself for a 10-minute wait in the San Juan heat than with a craftily flavored popsicle? The flavors offered change daily and are prominently displayed by the door, but ask for the guava flavor if you’re looking for something refreshing.

Casa Cortés Chocobar. An honorable mention goes to this chocolate-centric bistro with menu items such as chocolate grilled cheese and an assortment of dishes featuring sides of cacao-infused sauces. While we were ultimately underwhelmed by TripAdvisor-approved entrees we ordered, we found the restaurant’s desserts to be its saving grace and ended up returning twice for the sweets. You can’t go wrong with a frozen chocolate drink!

That’s it for my guide on how to see Old San Juan in a day! There is so much more to Puerto Rico than just the old town, so make sure you plan a longer stay in the future. Thanks for reading, and, as always, if you have any questions, feel free to contact me.

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