San Juan, the capital of Puerto Rico, is a popular port for cruisers. We had the opportunity to visit the port in March of 2022. San Juan did not disappoint and quickly became one of our favorite stops while cruising. San Juan captured our hearts and eyes with the colorful buildings lining the streets and the historic architecture. You won’t have to look far to appreciate the beauty of the island and its culture.
During our time there, we elected to walk the cobblestone streets ourselves and embarked on our own self-guided tour. Our goal was to walk as much as we could to visit some of the top sites in San Juan. We downloaded (and printed) maps of the streets before leaving for our cruise. We plotted out the stops we wanted to make along the way during the short amount of time allotted by the cruise ship. There was the option of booking a walking tour; however, we wanted to save a bit of money.
Creating your own walking tour is a manageable feat and one we were glad we did! We liked that we had the ability to mark sights off that didn’t pique our interest and maybe add on more that did. Walking around San Juan to all the destinations is quite the feat… we also liked that we had the flexibility to decide if we wanted to continue walking during our time there. If you visit all our stops, it is quite a day of walking!
Top Sights
While the maps I created are long gone (it’s been a minute since we cruised here), I will list all of the places we visited; however, these may not be in the correct walking order.
One of our favorite stops on the trip was Calle de la Fortaleza also known as the Umbrella Street. Typically the street is lined with brightly colored umbrellas; however, during our visit, it was lined with bright pink butterflies. During the winter seasons, the umbrellas are often replaced with the Puerto Rican flag.
The street is located near the residence of the Governor of Puerto Rico. The area that the umbrellas canopy over is actually closed to traffic, therefore, taking pictures here is quite easy!
We will warn that umbrella street is a popular place for pictures… making it a very tourist attraction. Don’t be surprised if you have to wait “in line” to get your pictures.
This picture spot is located right as you disembark from your ship! It’s quite the cute capture!
Paseo de La Princesa is a beautiful statue located on a promenade downtown. This statue is located centrally, so even if you don’t put it as a destination, you will likely pass it.
La Puerta De San Juan, located in the background of this picture, is the last of five gates that allowed access into old San Juan which was a walled city. The gate stands at 16 feet tall and dates back to the 16th century. This gate was actually the main entrance into San Juan. The gate was used to receive important visitors and goods.
The gate is located on the historic promenade as the statue above. This promenade is absolutely breathtaking. It is entirely worth walking to check out the amazing views.
Located directly above this is the Plaza La Rogativa which boasts beautiful views of the bay. Here, you can connect the San Juan Gate and La Fortaleza.
Every stop of this trip thus far has been free. Another favorite spot was Castillo San Felipe Del Morro or better known as El Morro. It is only $10 a person to enter. This fortification was previously used by the Spanish military. This was the second fort built on the island and was constructed in 1539.
The walled city of San Juan, including El Morro, became a UNESCO World Heritage Site in 1961. Not only is the fort beautiful as it sits looking out across the ocean, but you can also learn of the rich history by reading signs scattered across the fort.
There are several levels to the fort. When functioning, each level held a specific purpose. While you cannot visit all levels, be sure to check out each one that is available to the public.
The Cathedral Basilica de San Juan Bautista was another stop. This church is not only beautiful but is only the second oldest cathedral in the Americas. It is one of the oldest buildings in San Juan. The baroque architecture is breathtaking.
One regret we have is that we spent so much time checking out the sights that we didn’t make much time to enjoy the food! While we stopped at a food truck and San Juan Frappe’s, we wish we had put a little more thought into this experience. We were pleasantly surprised with both of our food experiences. San Juan Frappe’s features amazing fruit smoothies that are super fresh! It was so refreshing after a hot day!
We hope this helps you plan your time in San Juan during your next Caribbean vacation! Old San Juan is a destination you will be talking about for years to come! Please reach out to us via Instagram for any follow-up questions you have about this amazing excursion. Safe travels y’all!- Justin & Caitlin