Now that you’ve had breakfast, step out of the colonial headquarters where you’ll come upon the majestic castle of San Felipe del Morro, simply known as El Morro, a smashing fortress at the north-west tip of Old San Juan that carries over 500 years of Puerto Rican stories. Feel the trade winds as you gaze down right outside the fortification – facing the ocean – towards the Santa María Magdalena de Pazzis Cemetery, a municipal graveyard that serves as the final resting place of prominent and important people in history.
As you’re making your way downtown, be sure to check out the Iglesia San José. This is one of the most significant pieces of colonial architecture of the island, being one of the earliest surviving examples of the 16th century Spanish Gothic construction. Right in front of it is the Statue of Puerto Rico’s first governor, Juan Ponce de León. Fun fact: the statue is located right in front of the church where he is buried, and it is pointing towards Caparra, where Mr. Fountain of Youth wanted to establish the city.
By this time, the midday sun will be at its peak and that only means it’s time for a snack. Walk over to Tortuga, right in the corner of well-known San Sebastián street and San José. At this local bakery – that is filling out a need for accessible, inexpensive food available in Old San Juan – be sure to try Puerto Rico’s most popular baked-good: the quesito, a cream cheese, caramelized sugar-coated puff pastry that’ll make you lick your fingers.
Right there at San Sebastián street, the very path that hosts the brightest and biggest festival on the island, is La Factoría – one of the world’s Top 50 bars – and Taberna Lúpulo, the market makers that brought craft beer to the island. These two places are great spots for after-sunset ventures.
As you keep pacing down the blue cobblestone roads, you’ll find yourself in Sol street, where Casa Blanca, former residence-now-museum of the descendants of Ponce de León, is located. Down that beautiful and narrow alley is the Puerta de San Juan, the main entrance to the walled city during its Spanish colonial ruling.
Up the hill, by the Caleta de las Monjas, is the Catedral de San Juan where, if you stand right outside, aligning yourself with the altar, you’ll be standing in the exact spot where a compass would mark true North, South, East, and West of San Juan. Keep walking and make your way to the artery of the city, San Francisco street. This main avenue leads and cuts all the way across until it dies at the western city wall so, if you’re ever lost in Old San Juan, reset to San Francisco street and you’ll find your way… This time, you’ll find the way to mofongo!