I have been obsessed with Puerto Rico since I first set foot on the island 3 years ago. You want beaches? You want mountains? You want a rainforest? You want vibrant and historical cities or relaxing and all-inclusive resorts? Puerto Rico has it all, yet whenever I talk to people about future travels, few people have even considered placing the island on their to-do list.
There are so many amazing experiences to soak up in Puerto Rico, but before delving deeper into the island, I recommend spending a day exploring the history and culture of Old San Juan. Most flights to the island land at Luis Muñoz Marín International Airport (SJU) which is just 25 minutes from the center of historic Old Town San Juan. Whether you plan on spending your entire trip based in San Juan or you’re using it as a jumping-off point for other locales on the island, here’s my recommendation for how to spend a perfect day in San Juan.
Morning
Castillo de San Cristobal (Fort San Cristobal)
Start your morning with a visit to Fort San Cristobal. Fort San Cristobal’s construction began in the early 17th century by the Spanish, and to this day it remains the largest fortification Spain ever built in the Americas.
Entrance is $10 per person (unless you have an America the Beautiful Pass). In my opinion, it’s well worth the cost of admission, especially considering it allows you to enter San Juan’s other Fortress (we’ll get there later). Fort San Cristobal opens at 9 a.m. most days, so I recommend getting an early start and arriving right at opening. This will allow you to miss some of the crowds as well as avoid some of the intense midday sun. Part of exploring the Fort takes you outside, so it can get warm under the sun. You can purchase water in the Fort if you forget to bring your own.
The panoramic views atop the fort are a must-see. Soak in the beautiful views of San Juan throughout different lookout points. Don’t forget to ask for a guided tour while you’re there. You can grab so much more from the experience this way.
Exploring the Fort will usually take more than an hour, so you’ll be ready for some food afterward.
Brunch – Caficultura or Kaffe Haus
From Fort San Cristobal, walk about four minutes east to Caficultura. This is the perfect spot for a late-morning brunch. The food here is phenomenal, and the baristas really know their craft. There is indoor and outdoor seating, so choose accordingly based on how hot you got walking here. On weekends and days the cruise port is busy, the wait can be a little long, but it is definitely worth it! Kick back, enjoy the atmosphere, and soak up the experience.
Alternatively, if you are in a hurry or the wait times seem extra long, you can try Kaffe Haus a bit further along the way. You can always call ahead and get a reservation so a table is ready when you get there.
Afternoon
Now it’s time to get out and explore the streets of Old San Juan! After leaving Caficultura, make your way down the street to the Plaza Colon. On most days, there will be a number of tents set up around the plaza with various goods being sold. If you’re the type of person who likes farmer’s markets, or if you’re just looking for an affordable souvenir, this is a neat stop.
Fortaleza Street
After browsing the pop-up tents, continue forward toward Fortaleza Street. Not only are there some awesome shopping opportunities on Fortaleza Street, but it’s a great place to snap some photos. A section of the road usually has a canopy of unique items (umbrellas, flyers, flags, etc.) that are changed every 3-4 months.
This is also a great time to pick up a snack if you haven’t already. I’m a sucker for gelato, and there’s a wonderful ice cream and gelato parlor nearby named Anita Gelato. Definitely check it out if you’ve got a sweet tooth like me!
Once you’ve got your snack, lace up your sneakers and get ready for the highlight of the day! We’re going to head to the second fort on the island, the Castillo San Felipe del Morro. You can take an uber there if your feet are tired, but if you’re able, I recommend taking the long way around. From the end of Fortaleza Street, take the Puerta de San Juan onto the Paseo del Morro.
Paseo del Morro
The Paseo del Morro is a path along the water that wraps around half of Old San Juan. It’s about a 1.5 mile walk, but it is well worth it! The views are spectacular, and it’s not very busy. The last time I was there, I almost had the entire trail to myself—except for the cats, of course. There are quite a few stray cats along the way, but they mostly keep to themselves. If you like cats, they’re like a nice Easter Egg! Word of warning, though; these cats are feral, so I would advise not attempting to get too friendly with them.
Castillo San Felipe del Morro
Once you’ve reached the end of the Pass, you’ll reach the back end of the Castillo San Felipe del Morro. As of 2017, there is now an entrance here directly into the Castillo. This entrance will take you up through the fortress and directly to the front to begin your tour. Since you already purchased your ticket for both forts, you should be able to walk right in! The Fort here closes at 5 p.m., so depending on how leisurely you spent your afternoon so far, you should have an hour or two to explore. Del Morro is much bigger than San Cristobal, and it’s much greener. Even though you will have seen two forts in one day, they each have their own special charms.
Evening
Dinner – Puerto Criollo or Cosa Nostra
Now that you’ve finished trekking across most of Old San Juan, it’s time to chow down! You can walk to dinner if you want, but by now I’m sure your feet are exhausted. I recommend you call an Uber and let them drop you to your destination.
If you want traditional Puerto Rican food, Puerto Criollo is your place! The Mofongo is made fresh here, and it’s not usually overcrowded like a lot of the restaurants in this area. If you’re planning to have some traditional food another time, then you should check out Cosa Nostra instead. This Italian-style restaurant is one of the best on the island, and the portions are huge, too!
Teatro Tapia
If you’re not too tired from the day’s activities, it’s time to finish in style! While most guides suggest checking out La Factoria for drinks and dancing—and this is a great recommendation if you’re looking for that kind of excitement to cap your day—I like to finish more calmly. If you’re able, I highly recommend checking out a show at the Teatro Tapia.
Built in the early 19th century, the Teatro Tapia is worth visiting just to see the neat architecture inside and out, but don’t just stop there! Regular musical performances, plays, and even comedy acts are shown here. No matter the performance, I think this is the best way to end a perfect day in Old San Juan.
Conclusion
So there you have it—a perfect day in Old San Juan. You can visit both forts, do some exploring and shopping down the most popular street in town, eat some delicious food, and finish with a show in the oldest theatre in San Juan. Let me know what you think! If you’ve been to San Juan before and have some suggestions of your own, or if you have any questions about this itinerary, let me know in the comments below!