Old San Juan – San Juan, Puerto Rico. Life can be demanding. Work and personal obligations compete for a shrinking sliver of time. Our calendars, to-do lists, budgets, and life plans rule the day. Even leisure travel, when we grant ourselves a brief respite, can become an object of our planning prowess.
A mentor once encouraged me not to plan too much, to leave some things to serendipity. While plans help us to keep the trains running on time, he explained, they can also prevent us from seeing new opportunities on another track. I’ve been reflecting on this a lot lately, trying to incorporate it into all aspects of my life. I tried applying it to travel this weekend when, on a whim, I redeemed some frequent flyer miles, boarded a flight to Puerto Rico, and allowed myself to roam Old San Juan for a day, completely plan-less.
The streets of Old San Juan are perfect for wandering and making accidental discoveries. With no particular destination in mind, I strolled the narrow thoroughfares for hours. I had no list of must-sees, no dinner reservations, no tour groups to chase. I was open to distraction. Every intersection presented new possibilities — hidden retail shops, coffee houses, bookstores, museums, and galleries. The narrow streets unfolded in a rainbow of pastels and cobblestone, each telling a story, and some offering a surprise bend, flower-strewn alley, or salsa band. Some of the streets told their age, flanked by abandoned buildings, paint faded. Many of the streets eventually led to view of the surrounding water — either the bay or open ocean. Others carried me to the 400-year-old city walls. A few streets led to the massive Fort San Felipe Del Morro, its expansive green lawn with kites whirring overhead, its cannons and sentry towers on guard, and that elegantly peculiar neo-Moorish lighthouse perched atop. I allowed myself to linger wherever I felt comfortable for however long I pleased.
While peering through the window of one of the domed towers of El Morro, I spotted a trail below, the Paseo del Morro. Hugging the contours of the 400-year-old city walls on one side and the rocky coastline on the other, the path was an instant draw. I found the path’s head and followed. El Morro was now high above me. As the sun made its descent and the moon appeared above the city walls, I willed myself to walk slowly, to practice what photographers call “seeing.” When I reached the end of the path, I rested and let the wind cool me after a long and aimless day. And just as I was gathering my bag to head back, I happened upon my fortune — a stunning sunset, burning on the horizon had cast the city walls in the most amazing pinks and purples. I was reminded that, sometimes, we need to let go of our plans in order to find something worth treasuring.