After a day in Vieques and Fajardo, it was time to explore the heart of Puerto Rico’s capital city, Old San Juan.
From our hostel, Posada San Francisco, I started with this gorgeous view of Plaza Colón from our 5th floor open balcony:
Northeast of the plaza is Castillo San Cristóbal, one of the largest Spanish fortresses in the new world.
It costs about $5 to enter (which includes entry into the El Morro fort down the road) and has an old-school VHS-style introductory video to San Juan and its forts.
Give yourself at least an hour to linger here and take in views of the Caribbean Sea.
From the fort, walk along Calle San Francisco to get the best sense of the old colonial charm of San Juan, much of it which reminds me of the old Spanish colonial towns that I’ve seen in Cuba’s Trinidad, DR’s Santo Domingo, and Colombia’s Cartagena.
About 5 minutes along the street heading west, on your right is San Juan’s own Cafeteria Mallorca, famous for its mallorcas — a crispy bread pancake with powdered sugar — that are made by the dozens in front of you as you breakfast at the old school 1960s diner bar.
Then heading south on Calle San Justo, I swung by the 1938 Headquarters of Banco Popular, a building on Calle Tetuan admired for its art deco architectural flourishes.
Beside it is the Viejo San Juan Station of the US Postal Service, which existence sadly confirmed for me this would not be my 98th country.
Then head west along pretty Paseo de la Princesa outside the city walls.
At the western end of Paseo de la Princesa lies La Fortaleza, the oldest governor’s mansion that’s still in continuous use in the New World, and besides it a beautiful fountain dedicated to the Taino people.
Curve up north along the water and you’ll hit the distinctively red San Juan Gate, the traditional entrance to San Juan.
Enter the gate like the good old days and turn left immediately on Caleta de las Monja to see Plazuela de la Rogativa on your left.
Turn back onto the path leading from entering San Guan Gate, and walk east along Caleta de San Juan to check out the inside of Catedral de San Juan Bautista.
Turn right and walk south along Calle del Cristo to see the old Chapel of El Santo Cristo de la Salud at the southern end.
On your right is the pigeon-populated Parque las Palomas (Pigeon Park) facing the sea.
Head back north on Calle del Cristo and go all the way to Plaza San Jose on your right.
At the time of posting, the adjacent Iglesia de San Jose was closed for renovations.
Head more north through modern Plaza del Quinto Centenario…
…where you might catch Superman and Spiderman showing off their skateboarding tricks (look closely):
If you continue along Calle Cemeterio, you’ll see the colonial-era Cementerio Santa María Magdalena De Pazzis, the final resting place of many of Puerto Rico’s most prominent natives and residents.
Turn left and head up, walking through the wide esplanade towards San Juan’s other magnificent fortress, Castillo San Felipe del Morro (“El Morro”).
Designed to face San Juan Harbor this fortress was the gateway to the Caribbean, fending off British and Dutch invaders for nearly 4 centuries until the Americans arrived.
Entrance here costs $5, although it’s free if you show them proof you already paid $5 at Castillo San Cristóbal.
Take another hour/hour and a half to linger here, as it’s much larger than Castillo San Cristóbal.
At 5:30pm they’ll start kicking everyone out for a 6pm closing time. So get your bearings and head back into Old San Juan:
You’ll come across Plaza de la Beneficencia first.
And beside it is Casa Blanca, the ancestral home of the Ponce de Leon family and now a museum.
Enjoy the sunset here as you wrap up your walking tour of Old San Juan.
After 3 hours of walking around, the group reconvened for a dinner at El Jibarito before heading back for my 10:20pm Jet Blue flight home to NYC.
And to balance out all the swimmingly good luck we experienced getting from The Bronx to Vieques the day before, my Jet Blue flight to NYC ended up getting delayed 3 hours due to a sick passenger on the incoming flight to San Juan from NYC (which we needed to wait for in order to return to NYC).
So I slept on the airport floor for about 2 hours before getting another 3 hours of sleep during the flight, and then 1 more hour of sleep at my friend’s place by the hospital before starting another 12 hour day shift back on the critical side of the ER.
– At time of posting in San Juan, Puerto Rico, it was 80.6 °F – Humidity: 84% | Wind Speed: n/a | Cloud Cover: partly cloudy