Old San Juan Wedding Photography | Elopement Portraits in the Heart of Puerto Rico
There’s something about Old San Juan that feels alive in every sense of the word—the colors, the movement, the history that whispers from the stone walls and bursts from the balconies. When Gabby and Ryan asked us to join them for a day-after session in the city, it felt like the perfect continuation of their story—one rooted in love, culture, and connection to this island.
The day after their La Concha Resort wedding, we met up again to explore the cobblestone streets and centuries-old architecture of San Juan, camera in hand and no real timeline—just the city and the two of them. The light, the textures, the salt in the air—it all invited us into something cinematic and creatively rich.
Planning a destination wedding or elopement in Puerto Rico?
See Gabby & Ryan’s full wedding day here: An Elegant and Romantic Wedding at La Concha Resort
Wedding Portraits in Castillo San Cristóbal
We began the session inside Castillo San Cristóbal, a massive stone fortress that watches over Old San Juan. Built in the 1700s, it was once a defense post—but now, it feels like a sculptural relic. The light in this space is a photographer’s dream—sweeping in through arched openings, catching on the textured walls, creating natural frames and layers.
Everywhere we turned, there was contrast: hard lines softened by shadow, warm stone interrupted by sea breeze. It was a space that didn’t need dressing up. Just Gabby and Ryan, and the quiet permission to create. The fort gave us structure to play within—shapes, echoes, symmetry. It became less of a backdrop and more of a canvas.
Wandering the Streets of Old San Juan
From the fortress, we stepped out into the rhythm of Old San Juan—vibrant, sun-drenched, alive. The streets here are their own kind of art: walls layered with color, timeworn balconies spilling bougainvillea, narrow alleys that open into unexpected courtyards. Every turn offered something different—light bouncing off painted shutters, reflections in puddles, textures built by centuries.
Gabby and Ryan moved easily through it all. We didn’t need to direct much—just followed them as they laughed, paused, turned corners. The city itself seemed to celebrate with us. Cars honked, neighbors waved from second-story windows, and music floated from some unseen speaker around the bend.
A Pause at Catedral de San Juan Bautista
Tucked between colorful facades and echoing alleyways, the courtyard of Catedral de San Juan Bautista offered a quieter kind of beauty. There’s history in the stones here—this cathedral is one of the oldest in the Western Hemisphere, and it holds a softness that contrasts the fort above and the bustle just beyond its gates.
We slowed down for a moment beneath the arches and pale stone. Gabby and Ryan sat together in the filtered light, their voices low, surrounded by palms and gentle shadows. It wasn’t grand or showy—just a pocket of stillness in the city, where they could rest, reset, and take it all in.
Sunset by the Sea and the City Wall
As we reached the edge of the city, the sky opened up. The light had turned golden and soft and pink, spilling across the stone and wrapping around them. We walked the curve of the wall and paused in pockets of light, guiding them gently into shape while letting the connection lead.
It was simple, open, and unhurried. Every frame held that feeling—the mix of salt air, warm light, and something steady between them.
Thinking About an Elopement or Wedding Session in Old San Juan?
Whether you’re planning a destination wedding in Puerto Rico or dreaming up an intimate elopement among pastel streets and ocean breeze, Old San Juan is endlessly inspiring. We’d love to help you explore it—camera in hand, eyes open to the beauty and rhythm of this place.
Reach out to connect about your Puerto Rico wedding or elopement
Coming Soon
Stay tuned for more from Gabby & Ryan’s Puerto Rico wedding weekend—including waterfall portraits in El Yunque Rainforest and a sunset session in the mountains of Orocovis. We'll be sharing those soon, and you won’t want to miss them.
More from this Puerto Rico Wedding Weekend
See the start of this wedding weekend at La Concha Resort