With its bustling Old Town, delicious restaurants and lush beaches, the Puerto Rican capital is a welcome escape.
In early fall, I learned that one of my best friends, who I’ve known since kindergarten, was getting married in Puerto Rico in December. In the winter. Faster than you can say “bikinis and beaches,” I checked the “yes, I’ll attend” box and started planning what would turn out to be a few days of paradise in and around San Juan. Marriage aside, here’s how I went about it.
Day 1: Acclimate and explore
My flight landed just after noon and as we headed from the airport to Old San Juan, we stopped at Ocean Park to find a little slice of paradise in the sun and sand. A local classic, especially compared to Condado, a fancy beach to the west that gets a lot of traffic. The sparkling waves and soft sands of Ocean Park warmed my cold Brooklyn heart.
A dose of vitamin D was acquired in the historic old town. We walked the cobblestone streets, peered into shop windows and admired the colorful colonial-style buildings until we finally arrived at the Castillo San Felipe del Morro. One of several forts and defensive walls that make up the San Juan National Historic Site, El Morro was built by the Spanish between 1539 and 1790 to protect their colonial territory and after served as a U.S. military base during both global wars. (Have a national park annual pass? Bring it for free admission.) From its observation deck overlooking the sea, the fort is also a great place to watch the sunset. Watch the spectacle from the city walls or find a spot on the grassy boardwalk across the street, let the kids run around and let off steam, and watch the kites in action as the sun sinks into the sea.
During the day, Old San Juan is bustling with people—cruise ship passengers, tourists, and locals—but by the time we headed out for dinner, it was somewhat empty. As we walked south toward the docks, we came across Calle Fortaleza, a pedestrian street that leads to the governor’s mansion, where rows of colorful umbrellas hang; an hour or two earlier, the factory had been packed, and now we had it within reach.
Of course, those crowds had to go somewhere, and if the wait was anything to go by, they were all at Verde Mesa, a Mediterranean-Caribbean restaurant on Calle Tetuan on the southern edge of the neighborhood. After we finished, we walked around the corner to Barrachina, a restaurant that’s said to be the birthplace of the piña colada, and ordered a round of inexpensive frozen drinks—a filling but satiating appetizer. Then we tucked into dinner: Moroccan lamb stew, richly seasoned charred octopus and spicy chayote salad. We were there to party, after all.
For a nightcap, we headed to Factoría, a loud, dimly lit labyrinth that was recently named one of the world’s 50 best bars. With a DJ spinning in the back room and a young, enthusiastic crowd dancing, the atmosphere outweighed the serious and complex cocktails; the Tamarindo Loma in particular was an irresistibly smoky, spicy and tangy blend of mezcal, tamarind, chocolate and habanero that it called for seconds.
Day 2: Dinner and discovery
We rose early the next morning and set off, determined to cram as much into the day as possible. With strong coffee and Mallorcan sandwiches, made of sweet rolls loaded with breakfast toppings, pressed and dusted with powdered sugar, from the “boomonera,” a historic bakery and cafe, we headed northeast through narrow tree-lined streets and plazas to the Castillo San Cristóbal, part of the city’s fortification system, built between 1634 and 1783 to protect El Morro and the rest of San Juan from strikes by rival land nations like England and the Netherlands. We explored the underground tunnels of the lower level of the fort before climbing up to the third level observation area for 360-degree views of the city.
Back on earth, we browsed the shops, looking at the artwork at Galeria Botello, the hot sauces at Spicy Caribbee, admiring the Larimar-laden jewelry at various exhibitions, and finally succumbing to a necklace purchase at MUNS.
For lunch, we took an Uber to Santurce, an artsy neighborhood east of Old San Juan. We made our way to Jose Enrique, an unassuming place whose neon green facade screams
