Old San Juan, Puerto Rico

The Basics

My husband and I recently spent a week in Puerto Rico after finding cheap flights on Kayak Explore (one of my favorite travel tools). I consider PR to be a great “bang for your buck” destination. Not only can you find a reasonably-priced flight, but there’s less planning needed if you’re traveling from the continental U.S.; you don’t need to bring a passport or exchange currency, and most locals (at least around San Juan and other touristy areas) speak English as well as Spanish. At the same time, you get a true cross-cultural experience and there seem to be endless places on the island to explore.

Rather than staying at an expensive hotel in the Candado area of San Juan, we opted for an Airbnb in relatively mellow Ocean Park. In perusing the Airbnb options, it looked like many of them were on or very close to the beach and even offered amenities like beach chairs, coolers, and umbrellas. Access to a kitchen is also nice since food on the island is pricey (think $15-$25/plate at a sit-down restaurant, $8-$12 if it’s very casual or street fare).

We also rented a car, which we have mixed feelings about. It was great in allowing us to explore parts of the island we otherwise wouldn’t have, but we did find driving in PR to be stressful relative to the continental U.S., and some destinations were difficult to find (luckily my phone company doesn’t charge for roaming in PR so we could use GPS). Another option would be to stay in a larger city like San Juan and rent a car for a day or two to check the El Yunque rainforest and a bioluminescent bay off your list. If you do choose to rent a car, make sure to bring proof of insurance with you and double check that your car can be picked up at the airport. We had the hassle of taking a shuttle to the car rental place, which we were not excited about after an already long day of travel.

While there is a lot to do in all of PR, plan on spending at least one whole day (preferably two) in Old San Juan. This area is a photographer’s dream with its colorful buildings, blue brick streets, and ocean views.

Old Town San Juan Colorful Buildings
Old Town San Juan Colorful Buildings


If you’re driving, there’s a good chance you can find free parking if you don’t mind walking, or there are a couple lots within the area that appeared to have $5 parking. If you’re visiting during a festival or other particularly busy time, a taxi or uber may be best. Once you’re out and about, make sure to check out these stops:

El Morro and San Cristobal

These forts were built to protect San Juan from the English and Dutch in the 1500’s, though a nice perk is that they offer unbelievable views of the Atlantic Ocean and the city of San Juan. Some of these are through the forts’ many sentry boxes (garitas) where soldiers stood guard.


Plan on easily spending a couple hours at El Morro, then make your way to San Cristobal and use your same $5 ticket for entry. If you’ve already been through one of the forts, you’re likely move more quickly through the second. However, it is worth visiting both, for the views if nothing else; El Morro has more ocean views, whereas San Cristobal has better city views. If you’re an animal lover, you’ll also enjoy seeing a number of iguanas and cats, who both apparently frequent the forts’ surrounding areas. My husband informed me that we saw approximately 16 iguanas and 20 cats (but who’s counting?) While at El Morro, also make sure to view the neighboring Magdalena cemetery right on the beach and watch people fly kites on the park grounds.


Cathedral de San Juan Bautista

This is a small church dating back to the 1500’s that houses the remains of Ponce de Leon, who searched for the fountain of youth. There is also a neat story behind the church in that it used to have gold and silver elements, but those have since been stolen. Its decor is now simple but it is worth the quick stop if you’re already in Old San Juan.

San Sebastian Festival

We were fortunate enough to happen to plan our trip in mid-January, during one of the largest festivals San Juan has to offer. This festival is typically four days (5 days in 2017) that includes a kick-off parade on Thursday afternoon on Calle San Sebastián, four stages of music, local artisans and food vendors, and drunken debauchery. A friendly local bartender kindly encouraged us to go on Thursday, when crowds are relatively small. Given how packed the area was on Thursday, I can only imagine the craziness and person-to-person traffic that ensued on Saturday. The parade on Thursday was one of my favorite experiences from the trip. It starts with the large heads pictured below, which portray people significant to Puerto Rican culture and politics, then continues on with people walking on stilts, marching bands, and dancers. People also get up and dance or walk with the parade (or just take selfies with one of the heads), making it feel interactive.


Cafe Berlin

This is a fantastic restaurant on Calle San Francisco that offers both traditional Puerto Rican fare and vegetarian or vegan takes on these authentic dishes. I had trouble deciding what to order but settled on the vegan mofongo (essentially mashed plantain goodness). This was quite literally one of the best meals I’ve ever had, so I naturally had to include it in this post. As I mentioned above, dining out can be expensive on the island. However, I personally did not want to leave without having tried mofongo, coco frios (a coconut filled with coconut water and a straw), and a drink made with parcha (passion fruit). All of these are pictured here:

Have tips about Old San Juan to share? Post in the comments below. If you want to save this post for later, pin this image:

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