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.

Capturing Family Portraits: A Celebration of Love in Old San Juan

Momma bear and her two cubs

     Family portraits hold a special place in the hearts of both the families who pose and the photographers who capture them. Recently, I had the privilege of photographing a beautiful family session in the heart of Old San Juan, Puerto Rico. The session featured a mother and her two young sons, set against the vibrant, historic streets of this enchanting city. Old San Juan’s cobblestone streets, colorful buildings, and rich cultural heritage provided the perfect backdrop for this family’s story, turning each photo into a timeless memory.

     In every family session, there’s a deep sense of connection that shines through in the final images. But there's something truly unique about photographing single mothers with their children. Single moms embody resilience, love, and strength. These qualities were beautifully expressed by the mother I had the honor of working with during this session. Her bond with her sons was palpable, a testament to the love that keeps families like hers thriving. Celebrating these intimate moments between her and her boys was a reminder of why family portraiture is so meaningful.

     A great family portrait session is about more than just taking pretty pictures. It's about capturing the essence of a family—its joys, challenges, and the moments that bring them together. For single mothers, these moments are often hard-earned and deeply cherished. Family portrait sessions become a way to freeze time, to look back and reflect on the love that overcomes adversity. Every photograph becomes a tribute to the mother’s strength and her ability to nurture and protect her children.

     As a wedding photographer based in Puerto Rico, my primary focus is often on capturing the love stories of couples as they begin their married life together. However, family portraiture has always been a passion of mine. In between the beautiful weddings I photograph across Puerto Rico, I make time for family sessions. There’s something incredibly rewarding about capturing the joy and love within a family, especially in such stunning locations as Old San Juan.

     The vibrant and historic streets of Puerto Rico provide a one-of-a-kind setting for family portraits. The colorful Spanish colonial architecture, the serene ocean views, and the rich cultural history add layers of depth to each shot. Old San Juan, in particular, offers a fusion of heritage and charm, which elevates every family session into something unforgettable. Whether it's a playful moment between siblings or a quiet, heartfelt glance shared between a mother and her child, the beauty of Puerto Rico enhances these moments, making them timeless.

     Family portraiture is about more than documenting a family’s appearance at a particular moment in time; it’s about telling their story. Single mothers, especially, have stories that deserve to be told. They embody dedication, hard work, and unconditional love, often serving as both mother and father to their children. Highlighting this journey through photography is a privilege and an honor, one I am always excited to undertake.

The flower garden

     Between my wedding photography sessions, capturing families like this one is not just a change of pace but a joyful experience. Wedding photography celebrates the beginning of a new family, while family portraiture celebrates the ongoing journey. It’s the perfect complement to my work as a wedding photographer in Puerto Rico, reminding me that love comes in many forms and all deserve to be beautifully captured.

     Photographing families, particularly single-parent families, brings an added sense of responsibility. I want every image to reflect the love, the strength, and the joy that these families share. Single mothers, in particular, deserve to have their incredible journey celebrated through photography. Each session is a chance to honor their devotion and the unique bond they have with their children.

     If you're a single mother, or a family looking to preserve your story through photography, know that family portrait sessions are an opportunity to celebrate your love and connection. The experience is about more than the photos themselves; it's about taking time to appreciate your family as it is right now. In Puerto Rico, with its stunning landscapes and vibrant culture, there is no better place to capture those moments.

“Ok, make a funny face!”

     While I dedicate much of my time to destination weddings in Puerto Rico, family portrait sessions remain one of my favorite aspects of being a photographer. Whether it's on the cobbled streets of Old San Juan or a serene beach at sunset, these sessions are a chance to freeze time, capturing the love that binds a family together. For single moms, these moments are even more powerful—a testament to their strength, courage, and endless love.