The Charm of Old San Juan with photos and video

Tales of the High Seas: A Voyage aboard the MSC Seashore

November 16, 2022

My ship docked into the port of San Juan, Puerto Rico right next to the ship that my pal Joan was on, Royal Caribbean’s Oasis of the Seas.  She had been spending the day ashore while I hadn’t arrived yet.  She was already back aboard the ship refreshing herself and getting groomed.  It was 5:00 pm ish and as soon as we were allowed to go ashore, I took advantage.  I had to be back aboard by midnight.

HAL Nieuw Amersterdam
Royal Caribbean’s Oasis of the Seas with MSC Seashore peeking from behind

Money was extremely tight, so I opted to engage in a no-cost activity since I have already spent several days in San Juan before.  I used my mobile data plan which allows usage in Puerto Rico.  As soon as I got ashore, I started a self-guided walking tour of Old San Juan.  A free one was readily available online.  The city was founded by Spanish colonists in 1509 at a sight known as Puerto Rico.  San Juan is the third oldest European-established capital in the Americas.  In 1521, the words “San Juan” were added to the official name, thus making it “San Juan Baptista de Puerto Rico”.  This was in keeping with the local custom of christening the town with both its formal name and that which Christopher Colombus had originally given to the islands, honoring John the Baptist.

Today, this lovely historic area that I visited is characterized by its narrow blue cobblestone streets, and picturesque, brightly colored buildings, some of which date back almost 500 years. 

By engaging in this walking tour I got to explore Old San Juan in detail and soaked in its historical atmosphere.  I felt like I was traveling back in time, if only for a few hours or so.  There were a few times when I got a bit lost and found some wonderful treats of the area.

I am a “researcher” and I would have preferred that I did some comparison shopping when it came to finding my self-guided walking tour.  On this occasion I simply did a quick search on my phone and discovered, “GPSmyCity”.  There were a number of walking tours.  I selected the “Old San Juan” tour.  You can view the walk details that provide sight descriptions and photos.  It comes with a detailed walk route map and if I was willing to pay a fee, navigation features.  There was no need to hop on a tour bus or join a tour group.  I was able to explore all the city attractions on my own, at my own pace, and at no cost to me.  There were several tours available.  I chose the one that appealed to me the most and included 10 sights.  The app works completely off-line.  No cellular connection or data plan is needed, and roaming charges apply when traveling abroad.  With my mobile plan, I was covered traveling within Puerto Rico, so I had a data connection the whole time.  My tour of Old San Juan takes roughly two hours and covers about 2 miles.  I took a few detours and got lost a tiny bit.  So, I would say it took me a bit longer.

So many things to see on my walk as I stroll along
Old San Juan is so picturesque

My tour started at Plaza Colon (Columbus Square).  Back in the 17th century San Juan was encircled by stone walls.  This was the centermost of which was called Puerta de Santiago.  It straddled the sole highway linking the walled San Juan islet to the rest of Puerto Rico by land.  By 1772 the open space adjacent to Puerta de Santiago had taken the shape of Santiago Square.  To the south of the square is a gem of Puerto Rican entertainment culture, the Theater Tapia.  Over the years many notable performers have graced its stage.  Outside the theater, along Fortaleza Street, there are a number of quaint restaurants and cute little cafes.  The app provides more information about what you will discover but I will save you the reading for when you conduct your own walking tour.

Plaza Colon
Official stop number one of my tour

Stop number two was Castillo San Cristóbal (Fort San Cristobal)  Standing guard at the eastern gate, north of Columbus Square, is an imposing 18th century fortress, called Fort San Cristóbal.  The San Cristóbal guarded the city from enemy approaches by land, creating a crossfire with El Morro over the bay.  Meant to strengthen Spanish position in the face of imminent English and Dutch invasion, construction of the citadel began in 1634.  When finished, the entry to the city was sealed by the double gates.  San Cristóbal is the largest fortification ever built by the Spanish in the New World.

Stop #3:  Calle de la Fortaleza (Forteleza Street)

The imposing La Fortaleza building, formally known as the Palace of Santa Catalina, is the official residence of the Governor of Puerto Rico.  The narrow road leading to it, called Forteleza Street , is the main artery of San Juan’s historic quarter.  For the whole duration it is lined with government buildings, hotels, perfumeries, craft shops, jewelry store, and restaurants.  Just like many other colorful cobblestone streets in Old San Juan, each one is more photogenic than the next.

Stop #4:  Paseo de la Princesa (Princess Promenade)

Princess Promenade is a carefully restored historic landmark, one of the most visited in San Juan, ideal to walk or people watch.  It is also a great place to visit for families and small children.  There is an abundance of trees to provide plenty of shade, lots of artisan stalls and street vendors selling local foods, plus festivals and fairs often held here, including artisans fair on weekends.

Stop #5 San Juan Gate and City Wall

Built in the late 1700’s San Juan Gate is a giant doorway, the last remaining of the original five gates carved into the three-mile wall that once surrounded the city. Presently, the wall wraps around Old San Juan from the cruise ship piers on the San Juan Harbor to the capitol on the Atlantic. Currently a National Historic Site, the city wall is maintained by the National Park Service attempting to recreate the magic mixture of sand, water, and limestone used to stucco the wall. Along with the adjoining fortresses of El Morro and San Cristobal, the city wall attracts millions of visitors annually.

The City Wall
Strolling along the City Wall

After exiting the gate, I ran into policemen who prevented me from following the path laid out by the touring plan.  So I used my Google maps and tried to circumvent my original plan and created my own detour.  While wandering around I encountered some very interesting street performers in a park.  What a serendipitous, fascinating treat that I have posted for you here.

Stop # 6 Plaza de Armas

Arms Square is one of the main squares in San Juan. Over the years, it has changed several names relative to the functions it served.  Arms Square is the city’s de-facto central square modeled on the classic squares of Madrid and Mexico.  A highlight on the northern side is the Spanish colonial style Casa Alcaida – home of the San Juan City Hall.  A tinkling fountain, seating, shade trees, and a couple of old-school coffee booths make this a good spot for a break.

Stop #7 Cathedral of San Juan Bautista

The Cathedral of San Juan Bautista is the Roman Catholic church and the seat of the Archdioscese of San Juan de Puerto Rico.  This cathedral is one of the oldest buildings in San Juan, and the second oldest cathedral in the Americas.  The original cathedral in the then city of Puerto Rico was constructed from wood in 1521.  It was destroyed by a hurricane, upon which the current church was buildt in 1540 to be reshaped several times over the centuries.  The last remodeling was in 1917.  It is a rare example of medieval Spanish architecture.  The restored frescoes and the fact that it is still an operational church make it absolutely exceptional.

Stop #8 Museum of the Americas and Cuartel de Ballajá

Located in the old Spanish military barracks, Museum of the Americas is a multidisciplinary, multicultural and multidimensional non-profit institution, established in 1992 by San Juan’s famed archaeologist Ricardo Alegria.  It was closed on my visit due to the late time and day.  I understand that the main language of the displays is Spanish, some offer readable English translations, while others do not.  If you do not read Spanish, consider the recorded audio tour for rent.  It may take a couple of hours to tour the whole set of galleries.

Wandering about the museum grounds

Stop #9  El Castillo San Felipe del Morro (Fort El Morro)

On my visit, it is now pitch black and night has fallen.  I had visited during the day a number of years ago and it is well worth a visit.  El Morro is a 16th century citadel on the northwestern-most point of San Juan named in honor of King Phillip II of Spain.  It was the second military installation after La Fortaleza built on the islet of what is now Old San Juan and Puerta de Tierra.  You should visit to appreciate the importance of Puerto Rico as a strategic entry point to the Americas and the evolution of El Morro over the last five centuries.

El Morro

That concluded my tour of Old San Juan.  It was really dark at this time.  I decided it was time to head back to the ship and say good-bye to Old San Juan.  As I wandered the streets of the town I really wished money wasn’t so tight and would have loved to visit a restaurant, a bar, a dance club I had visited previously, a store.  But I hoofed it back to the ship quite easily as I have a fast, determined no-nonsense pace.  I returned far before all aboard time so my re-entry was quick and easy.

NEXT: Meeting friends of a lifetime from my “backyard”

Published by destinationdouglas

Independent Travel Advisor Extraordinaire! Enhance your travel dreams with concierge service. Specializing in cruising with Virgin Voyages, Celebrity Cruises, Norwegian Cruise Line, Royal Caribbean, Sojourn, Princess, MSC, Cunard, and AmaWaterways with Reach for the Magic Destinations. Adventure Awaits!

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