An Afternoon in Old San Juan
Old San Juan
Recently, my girlfriend Debbie and I decided we wanted to take another Caribbean cruise and began looking for one that stopped at island countries we had never visited before. In order to find a cruise that visited the more Southward islands in less than a week, we had to change our Port of Departure. We settled on Norwegian’s 7-Day Southern Caribbean cruise which began in Puerto Rico. (To see a review of the cruise, click here) We had never been to Puerto Rico before, so we figured why not! We flew into Puerto Rico on Spirit airlines the night before the cruise. We didn’t want to risk a cancelled flight and since our cruise didn’t leave until 9:00 p.m. the following day, we thought we’d have some time to explore. I had always heard bad things about Spirit, so I was a little hesitant, but the flight was fine, and I posted a full review here for those of you considering the airline. There is Uber in San Juan, but Uber drivers are only allowed to drop off at the airport, so you must queue up to take a taxi to the port or to your hotel. There was a set price to each area, and it was $21 per taxi to go to our hotel or the cruise port. (Note as of January 2020 they are now allowing Ubers to pick up at the airport).
We spent the first night at the Dream Inn near Ocean Park in San Juan which was located a few blocks from the beach. We chose this hotel because of the price and because it was near the Santurce area which is famous for its Street Art, and we all know how much I love Street Art. The rooms themselves were small but clean and comfortable. Each room had a double bed, and a small refrigerator. The lobby of the hotel was decorated like a Zen garden, and there was even a terrace with a hammock on the roof. The front door of the hotel remained locked, and there were bars on the outside of the hotel. We felt fine walking around during the day, but I’m not sure if I would have felt the same at night.
We arrived in San Juan at about noon, and after checking in we decided to visit the Miramar Food Truck Park which we had read about on-line. When we arrived, there were only a few trucks there, and nothing that looked like we had to try it. I’m going to give it the benefit of the doubt as their Facebook page talks about live music in the evenings so maybe there are better offerings at night. The Street Art however was great, and we enjoyed walking around the somewhat industrial area looking at the different paintings. Many a tourist stopped to get their picture taken in front of the Cuban Flag “lips”. Afterwards we headed back to the hotel and ate at a little Mexican restaurant close by called La B De Burro. They had outdoor tables and it was nice to sit and people watch. Other than Old San Juan which we visited the following day, we didn’t get to see much of the rest of Puerto Rico and will have to return someday to really get a chance to experience it.
We took an Uber into Old San Juan at 9:00 a.m. with our first stop being Barrachina restaurant. Barrachina is a popular family owned restaurant that has been operating in Old San Juan for over 40 years. Their website touts them as the “king of paella” and claims that a traditional Spanish bartender, Don Ramon Portas Mingo created the Pina Colada there in 1963. Obviously, we had to try it! If you’re wondering why we went to the restaurant first thing, it’s not because we’re a bunch of lushes (though I would have been perfectly willing to try a Pina Colada that early lol!). Barrachina has a free luggage hold service for cruise passengers from 9:00 a.m. to 5:00 p.m., all you have to do is leave the porter a tip – so we dropped off our bags then went off to explore the city saving the meal for later in the afternoon.
Old San Juan is very walkable, as the whole thing is about the size of Chinatown in New York City. There are some step hills though, so it might be a problem for those with mobility issues. The first thing we did was to head West two blocks on Calle Fortaleza towards La Fortaleza which is a 16th Century Fortification and the official residence of the Governor of Puerto Rico. The fort is a UNESCO World Heritage Site and was built between 1533 and 1540 to defend the harbor of San Juan. It is also known as Palacio de Santa Catalina and is the oldest executive mansion in continuous use in the New World. The Fortaleza is open from 9:00 a.m. to 4:00 p.m. on weekdays, admission is free, and there are guided tours every weekday except for Holidays.
Now, the Fortaleza is a beautiful building, but most tourists walking West on Calle Fortaleza from Barrachina aren’t there for the Fort, they are there to see the world-famous art installation that covers the street with colorful umbrellas. The street is an Instagrammer’s dream, with the umbrellas being changed out each season to different colors. When we arrived, the umbrellas were all pink, giving the street a strawberry glow.
Since it was still early and most of the shoppes were just starting to open we headed North on Calle De Cristo. Along the way we passed the San Juan Bautista Cathedral which was built in 1540 and is the second oldest in the Americas. The tomb of Ponce De Leon is inside. A little further North was the Hotel El Convento. The hotel began its life as a Carmelite Convent more than 350 years ago. The Convent was closed in 1903 and reopened as a hotel in 1962. The hotel is full of beautiful Spanish architecture with wooden beams, handcrafted tiles, and carved chairs. It’s also a beautiful backdrop for taking pictures.
We took a quick detour heading right on Calle Sol and then a left on Calle San Jose to see another Instagram favorite – 51 Calle San Jose. For years, the abandoned building was painted with scenes from Puerto Rico and the door was painted in the bright red, white and blue of the Puerto Rican flag drawing thousands of visitors to take their pictures with this classic background. At 2:00 a.m. on July 4, 2016, a group of four women who were part of an Artist’s Collective which later came to be known as La Puerta painted the flag black and white to show resistance and call for Puerto Rico’s independence from the US. The flag on the door has remained black and white to this day and is now a symbol for resistance in Puerto Rico. If you’re interested in Puerto Rican art and culture just a half block North is the Museum of Art and History, as well as the Institute for Puerto Rican Culture.
Next, we passed through the Plaza Del Quinto Centenario, which was built in 1992 to honor the 500-year anniversary of Columbus’s first voyage to the Americas. It’s dominated by a granite clay totem pole created by artist Jaime Suarez. Using clay from across the Americas, it’s meant to symbolize the origins of the people of America.
While in the square we had to stop for a piragua, Puerto Rico’s version of shaved ice. Unlike the round mainland versions shaped like snowballs, these are pointed at the top and look like pyramids. There is a plethora of flavors, from the basic to the exotic including Tamarind, Passion Fruit, Guava, Soursop and Anise. There are tons of vendors selling these desserts in colorful pushcarts all over Old San Juan – a nice treat on a hot day and they were only $1.50 each.
From the plaza we walked past the Cementerio Santa Maria Magdalena de Pazzi. The cemetery was built in 1863 and overlooks the ocean, symbolizing the journey to the afterlife. Many famous prominent Puerto Ricans are buried from entertainers to politicians. The views were amazing, and it felt like half of Old San Juan were flying kites on the massive lawn in front of the cemetery leading up to the Fort, Castillo San Felipe Del Morro on Old San Juan’s North Western tip. Admission to the Fort is $10.00, and also gives you access to the Castillo San Cristobal at the Eastern Gate.
Next, we walked to the Plaza Rogativa which is a famous bronze statue in Old San Juan near the Puerta de San Juan. Legend has it that British Troops took control of the city and the governor of San Juan ordered a “rogativa” which means to plea or supplicate. The women of San Juan joined by the bishop marched through the streets that night singing songs and carrying torches praying for the city’s deliverance. The British took the noises to mean that reinforcements had arrived, and they immediately vacated the city.
We walked back to the Puerto De San Juan with its bright red façade which is one of the three remaining gates of the Old City. Spanish ships used to anchor in the bay to unload colonists and supplies which would all go through this gate as far back as the 1630’s.
Just before the gate someone had painted the Cuban flag on some tree roots in the park – it was actually kind of cool!
Tourists can either take a right, and walk along the Paseo del Morro which is a dead end and routes you to some beautiful views outside the fort which are well worth the detour, or turn left and walk along the Paseo del Princesa, a beautiful tree-lined promenade with views of the water which routes you past the other side of the Forteleza.
We chose to wander back through the streets of Old San Juan and admired the architecture of all the homes as we went through. There were a ton of cats wandering around almost in small gangs, which I kept trying to take a picture of for Daughter #2 who dislikes cats just to get her reaction.
I’m pretty sure she scratched Puerto Rico off her bucket list right then and there lol! Our walk took us to the Parque Las Palomas, which is the Park of the Pigeons. This is a small park with hundreds of pigeons gathered and just as many tourists determined to feed them. If you don’t like birds, then this is NOT the place for you as they are so used to being fed, they will jump down on you until you give them something to eat. I enjoyed taking pictures and watching from a distance, but Daughters #1 & #3 who HATE birds would have been absolutely terrified (and just to clarify they are 14 and 19 lol!).
We were really hungry by now, so we wandered back to Barrachina for lunch. Shortly after we arrived, they began telling people that they were full for lunch, so if you’re dying to try this place, I’d make sure you get there early. We ended up getting the last few spots at the bar, and you could only sit if you were going to order food. I wanted to try a little bit of everything, so I got the Puerto Rican Delights platter – turnovers, corn fritters and beef and chicken croquettes which was only $7.95 and very good. Deb went for a truly local dish, Chicken Mofongo – Which is mashed fried green plantain or cassava, seasoned with garlic and spices covered with chicken… yum! Oh, and if you’re wondering, they really do have a good Pina Colada 
After we ate, we wandered back to the Plaza De Armas, one of the main squares in Old San Juan to people watch and check out the local shops. We love to see what other places stock in convenience and grocery stores, so we wandered into their version of CVS, Supermax. The square’s main feature is a circular fountain with 4 statues surrounding it, one for each season. After that it was time to grab our bags and make our way to the ship. There were so many people trying to find a taxi, that we actually found it easier to walk a few streets away were it was less crowded and order an Uber.
Most cruise ships dock at the San Juan Dock Cruise terminal which is a quick and easy walk into Old San Juan. However, certain Norwegian, Royal Caribbean, Celebrity and Disney ships dock at the Pan American Terminal which is across the Vajo De Manglar and about a 10-minute taxi ride into city center. Our ship docked at the Pan American terminal, so we took an Uber back to the ship to begin our journey. When planning your itinerary keep this in mind. You can usually find out from your cruise line where your ship will be docked.
We really enjoyed our trip to Old San Juan, and it’s so compact you can get a good sense of the area even in a small amount of time. The one thing I regret not doing is the Flavors of San Juan Food Tour. It seemed a bit expensive when I first came upon it, but I later found out it is rated one of the top Food Tours in the world. If you’re headed to Old San Juan and take the tour let me know how it is!
Cruising the Caribbean...
