The Mission: To do a long-term workcation in Puerto Rico.
The Participants: The Mister, Me, the Little Man and our Little Dog too.
The When: From January 2021 to March 2021
This is Part Five of a five part series talking about our Puerto Rican workcation: Links to Part One, Part Two, Part Three, and Part Four. The steps we took to prepare to remote work can be found at the following post: Making Margaritas out of Limes Remote Work Checklist. Make sure to check out our Best of Puerto Rico recommendations as well!
Old San Juan, one last stop before home
Friday March 5, 2021 to Thursday, March 11, 2021
For me, Old San Juan was the best place that we stayed on the island. I love a walkable urban lifestyle with lots to see and do around me. Old San Juan fit the bill.
We stayed in an Airbnb on Forteleza and Cruz which was centrally located in Old San Juan. Though Old San Juan covers a 7 square block area so everything is within walking distance regardless of where you might be within the district.
🐾 Dog Tip: When finding accommodations in a bigger city make sure to have some green space nearby because your four legged friend deserves to a bathroom close by.
I loved exploring this part of the city because it was a feast for the eyes. Every step unveiled another picturesque building, statute, fountain, or other unbelievable gorgeous view. This area was also filled with great restaurants, bars and stores filled with so many bright and vibrant handicrafts.
Since everything is so close distance-wise, I’m just going to identify the things that we loved to do, see and eat while in San Juan. That way you can pick and choose what to do with your time in San Juan.
Walking Tour of Old San Juan
You could spend days doing nothing but walking the streets of Old San Juan and have a great experience. But these are the streets that you cannot miss.
Forteleza
The entirety of Forteleza street is filled with stores, restaurants and bars. But you must visit the very end of the road adjacent to the governor’s mansion where there is an art installation. For a long time, that location was famous for its floating multi-colored umbrellas. But it seems like they are now rotating the display. The umbrellas were replaced with a huge Puerto Rican flag spanning the length of the road but when we were there, there were pink kites that were placed by Susan G. Komen, an organization dedicated to fighting breast cancer.
Also on Forteleza, you can find Barrachina, which is allegedly the birthplace of piña colada. To be honest, I wasn’t that impressed with their piña colada or their food. But their location was pretty neat especially if you could sit in their outdoor courtyard located within the building. And they do have a free Flamenco Show on Fridays and Saturday nights with the purchase of dinner.
Also, located on Forteleza is the highly rated Cafe el Punto. I wasn’t blown away with this restaurant either, but the ambiance was nice with a guitar player serenading diners in the restaurant.
If you turn left on the street before the art installation, you can head down to the Capilla del Santo Cristo de la Salud. This building is especially neat because a segment of the building depicts what the building once looked like at its peak.
The legend is that the chapel was built in honor of the miraculous survival of a rider who fell of the cliff on his horse. Allegedly the Spanish Governor saw the event and cried out “Christ of Good Health, save him!” The horse died, but rider survived. And when the rider survived, the belief spread that this area was blessed and even today, devotees come to this chapel to pray for health. If you want to visit the actual chapel itself, keep in mind that it is only open on Tuesday.
Another draw for this area is the swarms of pigeons who are used to being fed by tourists. If you want to be one of those tourists, you can buy food to feed these ravenous beasts from a local vendor.
Paseo de la Princesa
This scenic boulevard cannot be missed. Make it a point to stroll this area both during the day and at night. You will get a lovely view of the city wall as you walk down the broad tree lined path. On the weekends, vendors set up along the boulevard so you may want to plan your visit accordingly if that is of interest. Although closed because of COVID, there is a lovely kids park and garden adjacent to this path. This path culminates in a gorgeous fountain right along the shore.
From here if you continue to walk along the shorefront, you will eventually get to the Puerta de San Juan, one of the few remaining gates to the old city.
But before you get too far from the Paseo de Princesa, here are a few amazing restaurant recommendations in this area:
Princesa Restaurant
If you could eat at one restaurant in San Juan, this is the one. The food and drinks were exceptional, the ambience was spectacular and the staff was just so warm and welcoming.
A fun personal story about this restaurant – when I first visited Puerto Rico, I was a poor student. I remember walking past this beautiful restaurant set back in the greenery along Paseo de Princesa looking at the menu knowing I couldn’t afford to visit. I vowed I would return someday to have a dinner or drink there. This was the visit and it was worth the wait.
La Casita
La Casita is another wonderful restaurant on the others side of the Paseo de Princesa. Adjacent to the water, you can get a fantastic seat on their patio overlooking the water. Their craft cocktails were fantastic and the food was delicious.
Trina Tapas & Flamenco
Trina Tapas & Flamenco is another restaurant that has Flamenco shows on Friday, Saturday and Sunday nights. We went to the restaurant early on Friday night to see if they could fit us in. The dining room was booked, but they were kind enough to put us in the bar at a table with a view of the show. It was great. The food was good and we got to catch enough of the show to enjoy that part of the night. The Little Man was pretty tired so we only caught the early part of the show before we called it a night.
Here are some shots of the Paseo de Princesa at night.
Forts of Old San Juan
There are two forts that protected Old San Juan – Castillo San Felipe del Morro and Castillo de San Cristobal. The distance between the two forts is a little over a mile. We tend to walk fairly quickly but most people should be able to visit both of these forts in a few hours, including the walk.
And actually the walk is a huge part of the experience. El Morro is surrounded by a huge park when families come to fly kites and enjoy the outdoors. When we were in the park, the Little Man couldn’t help himself. He just had to roll down the grassy hills. As you walk down towards the Castillo de San Cristobal from El Morro, you will get a beautiful view of the Santa María Magdalena de Pazzis Cemetery.
If you have an option, you may want to time your walk to coincide with the Saturday morning farmers market. This takes place by the entrance of El Morro near the Museo de Arte e Historia and you can browse the vendors offering locally-grown produce and foods stuff.
👪 Family Friendly. The entrance fee for both forts was $10 when we went. So make sure to hold on to your receipt until after you have visited the second fort. The National Park Service has great programming for kids and we were able to get a Junior Ranger packet with kid friendly information, activities and a badge. As a 6th grader, the Little Man was on the top end of the age range but he still enjoyed looking through the packet and brought the badge home with him.
Keep in Mind that U.S. 4th graders and their family members enjoy free access to federal parks and waters via the Every Kid Outdoors program.
🐾 Dog Friendly. Unfortunately, pets are not allowed in the fortifications themselves, but they are allowed on the grounds outside the forts.
👪 Family Friendly. 4th Graders and their families enjoy free access to federal parks and waters via the Every Kid Outdoors program. Also, make sure to check out the National Park Service programming for Kids.
Castillo San Felipe del Morro
El Morro is the fort that overlooked the entrance to the San Juan Bay. It is massive six level fortress and one of the largest fortifications built by Spain in the Caribbean. El Morro and the smaller fort across the bay called Fortín San Juan de la Cruz, known as El Cañuelo would attack unwelcome ships from both sides of the bay effectively denying access to any invaders by sea.
The construction of El Morro started in 1539 and finished in 1790. And the Spanish were mostly successful in fending off foreign invaders and pirates during the entirety of that time. It wasn’t until 1898 that the Island changed hands from Spain to the United States as a result of the Spanish-American War. At that time, El Morro was used by the US military and actively served as a base during the First and Second World Wars. In 1961, the National Park Service acquired El Morro for use as a museum and both El Morro and the walled city of Old San Juan were declared UNESCO World Heritage Site in 1983.
Castillo San Cristóbal
Castillo San Cristóbal protected the city from land attacks. For that reason, the set-up was a bit different. From the top of the fort, you can see a number of different walled courtyards. You could imagine a fierce battle with the defending soldiers holding the outer walls of Castillo San Cristóbal until a retreat is sounded. The defenders would retreat back to the next layer of fortifications and then hold that line. And just as the invaders thought they were victorious, they would see the next level of fortification and have to wage battle all over again. Standing on the walls of the fort, I could just imagine how disheartening it would be for an invading force to have to work their way past all of these defenses.
One of the interesting stories around this fort is the Garita del Diablo or the Devil’s Sentry Box. This outpost is the farthest from the others and protrudes into the ocean.
In the old days, the night watch soldiers would shout out at each other throughout the night to ensure that everyone was awake and alert. But because the Devil’s Sentry Box was so much further than the rest, it was difficult to remain in contact with that particular outpost. One dark and stormy evening, a soldier at that post failed to respond to any of the calls during the night. While the soldiers feared for his safety, none dared venture out there to check on him until light. When they arrived, there was no sign of the soldier. All that could be found were his rifle and uniform.
While some believed he was spirited away by the Devil, other locals offered a different explanation. The claim was that the soldier had simply run away with his lover and that she brought him civilian clothing so that they could make a inconspicuous escape. But either way, the soldier was never heard from again and legend has it that if you approach the sentry box at night, you might hear this missing soldier laughing and playing a guitar, perhaps mocking those who believed in the supernatural explanation that allowed him to escape his military duties for a life of love with his lady fair.
Catedral de San Juan Bautista is the oldest church in the US and the second oldest church in the western hemisphere. This church is the final resting place for two notable figures: explorer and conqueror Juan Ponce de León, as well as the martyr Saint Pius.
As you may recall from your history books, Ponce de León was popularly known to be the explorer who was searching for the Fountain of Youth. However, while it is a popular myth, there does not appear to be any modern day evidence in his journals or otherwise that supports this belief. Ponce de León was the explorer who lead the first official European expedition to Florida and served as the first governor of Puerto Rico. And apparently very busy on the home front as well as an estimated 30% of the modern population of Puerto Rico descended from Ponce de León and his wife.
According to the plaque posted in the cathedral, St. Pius was a soldier who was wrongly executed as one of the first martyrs of the Roman persecutions against Christians in the first century. His body is encased on the glass coffin below the stained glass window.
The story of how St. Pius ended up in Puerto Rico is quite the saga.
In 1848, Puerto Rico’s Bishop asked Pope Pius VII for the privilege of having a relic of an early martyr on the island and was granted his choice. The Bishop visited the catacombs and chose the remains of St. Pius. On the journey back to the island, the Bishop then left the remains in Barcelona to be restored and to build the ceramic form that would house his remain. After returning to Puerto Rico, the Bishop passed away without ever reclaiming the relic.
About twenty years later, the new Bishop made a trip to visit the pope and when passing through Barcelona, he was informed that the city was holding a relic belonging to the island. Finally, St. Pius was coming home to the island that would be his final resting place.
More Old San Juan Hot Spots
Cannon Club
🐾 Dog Friendly!
If there is one place that you go for drinks in Old San Juan, this is the place. From the outside it doesn’t look like much and its hidden away in a neighborhood without too much else around. But as soon as you step inside, beautiful wood paneling and chandeliers transport you to another time and place. With two Steinway pianos in the main room, you know that live music is a big draw for this venue. As you venture further in, you see the doorway to the central outdoor courtyard. The most unexpected surprise awaits you there as you see something that reminds of a roman bath with a two-waterfall swimming pool meandering around ancient walls and doorways. You walk up and around the stairs and yet another level of outdoor space awaits. While the ambience is definitely the draw, the craft cocktails were expertly crafted and the tapas were tasty. This is a unique experience that you should definitely make a point to have if you are in Old San Juan.
Mercado La Carreta
🐾 Dog Friendly!
Hands down the best brunch place in Puerto Rico. Amazing enough that we visited three times in one week. Not bad for a family that rarely visits a place more than once when on vacation. The food was delicious, the service was amazing and they were so dog friendly! The wonderful staff went out of their way to make our Little Dog feel welcome and some even remembered him by name by the second visit. I cannot say enough wonderful things about this place! Make sure to visit! You will not regret it. The only tip would be that this place is very popular and there will be a waiting list. Put your name in and then make the most of your time by exploring Old San Juan. On our second time having brunch here, we actually walked down to the Paseo de Princesa to the Gates of Old San Juan and then circled back to the restaurant just in time for our table to be called.
Chocobar Cortés
If you are a chocolate fan, this is the place for you. Everything here incorporates chocolate.
The Mister and I tried their drinks. I had the Bloody Choco Mary and he had the Chocolate Old Fashioned.
Oh. My. gosh.
That was seriously the best Bloody Mary that I have had in the longest time. And that is high praise coming from a Wisconsinite where Bloody Marys are a way of life. Seriously. Get it. It is that good!
To end my post about my visit to Old San Juan, here are some more lovely pictures to showcase how beautiful and vibrant Old San Juan is as well as video documenting that you never quite know what you will see on the streets of Old San Juan.
Things to see outside of Old San Juan
Escambron Beach
🐾 Dog Friendly!
This is a nice city beach. It was pretty crowded when we visited during the weekend, but we were still able to enjoy our visit. This beach is protected by a coral reef which allows creates a natural pool for swimming and snorkeling. However, even with that protection, I felt that the ocean was a bit too rough to allow for comfortable snorkeling. Once we had our fill of beach time, we walked east where we found the Batería del Escambron which is a small fortification that seemed little more than a wall. We then went further east along the shore to the Escambrón Marine Park. Again, I don’t think that Puerto Rico is the best place for snorkeling. There just is not that much diversity or vibrancy in the marine life. But this apparently is a place that has decent snorkeling for the island.
La Placita de Santurce
This market was founded more than 100 years ago as a two story market. The neighborhood developed around the market into a hotspot with lots of restaurants and bars that comes alive in the evenings. Unfortunately, we came here after the market closed so we didn’t get to see that in action. We went to eat at the Chicharrón which did have a very tender Churrasco, but I wasn’t too excited about the meal there. Unfortunately, perhaps because of COVID, they did not have a number of the menu items that we were interested in and the food was mediocre. It may have been more fun if we had stuck around to see the environment at night or if we had gotten a chance to see the market in operation. But I don’t know that it was worth the trip.
Capital District of San Juan
Just outside of Old San Juan is the Capital District. This majestic domed Capital Building is the anchor for this area which has a number of monuments and important buildings surrounding it. This too is a great walking neighborhood especially along the Avenida del Constitucion and Avenida Munoz Rivera. Some personal highlights included the San Juan Holocaust Memorial and the Paseo de los Presidentes that honor the various ways that US Presidents have impacted Puerto Rico and its people.
Bacardi Tour
👪 Family Friendly.
This is one of the things that I have yet to do. Interestingly enough, kids are typically welcome to join the general tour. But that tour was not running due to COVID and unfortunately the Mixology Class and Rum Tasting Tour was not kid friendly.
If you are planning on visiting, then you may want to consider the upgraded classes. I always enjoy an experience rather than just a tour.
Both experiences include the standard tour, but the Mixology class will teach you how to make a perfect Mojito and Shaken Piña Colada while learning about the history of these cocktails as well as some cool bar tricks and skills and the Rum Tasting Class will provide the opportunity to taste BACARDÍ’s premium rums, accompanied with a chocolate pairing.
Adventures in Planning 