There’s something about Old San Juan that feels like it was made for film photography. Maybe it’s the pastel-washed buildings that catch the Caribbean sun just right, or the rhythm of daily life that unfolds so effortlessly in front of the lens. Either way, this historic town remains one of my favorite places to explore with a camera in hand.

Normally, I’d be out here with my medium format gear, loaded with fresh 120mm film—something like Kodak Portra 400—chasing every detail with intention. But this trip was about packing light and letting spontaneity lead. I brought just one roll—expired Portra 400—and loaded it into my trusty Nikon FE2. No backup film. No pressure.

With only two hours to wander, I found myself pulled toward the simple scenes: a man standing over a fresh batch of plantains at his feet, a Puerto Rican flag swaying from a weathered balcony, a child exploding through a flock of pigeons in the square—sending them into the air all at once. Doors with character. Buildings with soul. People moving through their lives, unaware of the quiet beauty they offer.

There’s a texture that expired Portra gives you—something unpredictable and a little nostalgic. It softened the edges and added a kind of romance to the day. Every frame was a bit of a gamble, but that’s half the thrill of shooting film.

All scans and processing were handled by the team at Indie Photo Lab, whose work always brings out the best in imperfect negatives. These are some of the selects from that afternoon—a brief but vivid window into Old San Juan’s timeless charm.