Celebrating a Milestone Birthday in Old San Juan with a Luxury Portrait Session
The incredible Lina
A few weeks ago, I had the pleasure of photographing Lina, an event planner from Sunrise, Florida, who was visiting Puerto Rico to celebrate a milestone birthday. What made this session especially meaningful was that Lina found me through Instagram—after seeing a family session I shot for a former wedding client from 2022. She reached out through my website and shared that, while it was rare for her to plan something just for herself, this birthday felt like a special moment she wanted to commemorate.
Her one request? To make the photos feel Puerto Rican—visually rich, nostalgic, and personal. Old San Juan immediately came to mind for both of us. With its cobblestone streets, Spanish colonial architecture, historic landmarks, and waterfront views, it’s the perfect setting for portraits that celebrate both heritage and beauty.
Bringing the Vision to Life in Old San Juan
Everything is a picture waiting to happen in Old San Juan
To help bring her vision to life, I brought along my assistant Bryan, who not only lives in Old San Juan but also specializes in helping me set up off-camera flash, which is one of my favorite ways to create dimension and drama in natural-light environments. There's something incredibly powerful about combining Golden Hour sunlight with a touch of flash—it creates portraits that are luminous and layered, perfect for capturing personal milestones.
We met around 5:45 p.m., just in time for that golden-hour glow. Our first stop was Palacio Provincial, a stunning boutique hotel that serves as the quieter sister to the well-known El Convento. With its intimate charm, grand staircase, and historic façade, it was the ideal place to begin.
From there, we strolled through the vibrant streets of Old San Juan, snapping spontaneous walking shots and using local greenery to frame Lina against the city’s beautiful textures. We headed toward La Puerta de San Juan, the iconic red gate that once served as the city’s main entrance. Along the way, I pointed out that “everywhere you look in Old San Juan is a possible picture—if you look closely enough.” That kind of visual storytelling is what keeps this location fresh every single time I shoot here.
Signature Shots with a View
Tomás is loving life
As we made our way up to La Rogativa, I captured one of my signature shots—a dramatic flash-lit portrait featuring the garita, the iconic sentry box that overlooks the bay. This shot has become something of a calling card for me on social media, and I love how it blends artistry, architecture, and emotion.
Our final stop was Castillo San Felipe del Morro, more commonly known as El Morro. It’s arguably the most recognizable landmark in Puerto Rico and offers one of the best sunset views on the entire island. From this vantage point, you can take in the golden horizon as sailboats and ships slowly make their way into the harbor.
Bryan and I got extra creative with our lighting setup, even incorporating a massive cruise ship that happened to be passing by. The mix of golden sky, textured stone, and crisp flash lighting made for a set of images that felt both cinematic and deeply personal.
Celebrating with More Than Just Photos
Leading lines to Lina
After the shoot, Lina was so thrilled with the photos—just from what she saw on the back of my camera—that we invited her to join us at Taberna Lúpulo, a popular local bar known for its craft beer selection and laid-back vibe. We spent the rest of the evening enjoying snacks, drinks, and great conversation as if we had known each other for years.
It was the perfect way to wrap up a session that felt less like work and more like celebrating with an old friend. This is why I do what I do—not just for the photos, but for the moments of connection and joy that happen along the way.
Planning a Portrait Session in Puerto Rico?
What a lovely couple!
Whether you're celebrating a birthday, engagement, anniversary, or simply want to capture a meaningful chapter in your life, Old San Juan offers a timeless backdrop for luxury portrait photography. I specialize in creating unforgettable sessions that blend editorial style with authentic storytelling—using light, location, and emotion to craft images you’ll treasure forever. Ready to create something beautiful together? Reach out to me here to begin planning your own unforgettable session in Puerto Rico.
