On the front and tail end of my family’s week-long cruise around the eastern Caribbean (coverage on that to come soon!), my family and I found ourselves with two half days to spare on either side in our departing port of San Juan, Puerto Rico.

About Old San Juan

Old San Juan is an array of so many things that I love – cobblestone streets that remind me of European cities, fascinating history, lively nightlife, and colorful Colonial-era architecture – all with a dose of tropical flavor. It’s also the founding city of Bacardi rum and the piña colada, so you know you can expect a good cocktail here.

Having been to San Juan once before, albeit seven years ago, I knew a few of the highlights I wanted to share with my family as well as discover a few new ones for myself; hopefully giving them a great taster of San Juan in short period of time. So, without further ado, here’s how I recommend to spend one day (or two half days) in San Juan, Puerto Rico.

Half Day One

Our flight arrived late at night, so after a night of rest at our AirBnB in Old San Juan, we awoke the next day ready to hit the ground running. Since we had to check out of our AirBnB, I had done research as to where we could store our luggage before boarding our cruise in the evening. Barrachina was a name that came up for this search, which was perfect because it also happens to be the restaurant where in 1963 the piña colada was created. We headed to Barrachina to store our luggage (it is free, but tips are appreciated) and sat down to enjoy one of the delicious piña coladas.

One of Puerto Rico’s traditional dishes is mofongo, a fried plantain dish that can have meat, and is topped with a flavorful broth. In search of this delicacy during our time on the island, we were recommended to visit Mojito’s by a local taxi driver. Unfortunately Mojito’s was closed on Sunday, so I enjoyed my chicken mofongo at Barrachina instead.

Once our tummies and taste buds had been satisfied, it was time to explore the Old Town. It may be cliche to say, but Old San Juan has such bright and beautiful buildings that simply walking around is a must do.

Old San Juan historically was surrounding by city walls to protect from invaders; a fair amount of which is still intact. Along the wall is the Paseo del Morro walking path, which we stumbled upon as we walked towards the water. From the start of the path, we walked about a mile along to the El Morro Fortress, one of the two fortresses in Old San Juan.

San Felipe del Morro fortress is a 16th-century Spanish fortification atop a cliffside on the northwestern-most point in Old San Juan. Now part of the U.S. National Park Service and a UNESCO World Heritage Site, the fortress was designed to guard the entrance to San Juan Bay and defend the formerly Spanish colonial port city from enemy attacks. The fortress has cannons pointing seaward and provides a splendid view of the immediate area.

After wandering around the fortress, we walked back to Barrachina’s to pick up our luggage and then headed to the cruise port for check in.

Half Day Two

After our cruise, we docked back into the San Juan Cruise Terminal around 8am. Since it was early, we didn’t know of where to store our luggage so instead opted to do a driven tour of old and new San Juan. At the cruise port there are several taxis available, and we met with one to do a two hour tour of the city before being dropped off at the airport for our flight. For the two hour tour for three people we paid $60, which we thought was a fairly good deal considering the taxi ride alone to Old Town from the airport for the three of us was $26 (the prices are set rates by the government). At 8am in Old San Juan on a Sunday the town was the quietest we had seen it, which was ideal for a driven tour.

Our tour guide drove us around Old Town, pointing out monuments and buildings as we went along, and over to the El Morro fortress. He shared with us that San Juan is a very active and walkable city, which we witnessed by the many people out for a morning run. He also showed us bike lanes that had been installed around the city, and a basketball court that was built by Carmelo Anthony, who is half Puerto Rican.

We then headed out of the Old Town into the new town areas of ocean front Condado, where many of the hotels are, and Isla Verde. In Condado we stopped at the beach, and in the skyline I noticed the Caribe Hilton hotel which my mom vacationed in over forty years ago! We also passed by the condo building in which Ricky Martin owns the penthouse condo.

If You Have More Time

With a few more hours… Visit the Barcardi Factory, home of the infamous Puerto Rican rum. The factory is a 25 minute drive from Old San Juan, but is well worth a visit as they give you a few sample drinks and a tour around the facility.

With another an extra day… Visit the El Yunque National Forest. About an hour outside Old San Juan, the rainforest is a Puerto Rican gem, complete with rich vegetation and waterfalls. Day tours can be easily arranged while in Old San Juan.

Have you been to Puerto Rico? What were your highlights?