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.

A Perfect Surprise Marriage Proposal in Old San Juan, Puerto Rico: Peter and Debora’s Story

The waiting game.

     Every once in a while, as a Puerto Rico photographer, you’re invited into a story so heartwarming that it leaves an imprint long after the session ends. Such was the case when Peter reached out to me with a heartfelt plan to propose to his girlfriend of three years, Debora. Their love story, which began in Arlington, Virginia, was set to take a monumental turn in Puerto Rico—Debora’s birthplace and a location rich with romance, history, and charm.

Smells like a yes.

     Peter’s email revealed that the couple would be staying at the iconic Hotel El Convento in Old San Juan, a former convent transformed into a boutique luxury hotel. Its historic walls and breathtaking surroundings make it a coveted spot for photographers in Puerto Rico, and Peter was eager to create a memorable moment that Debora would cherish forever. However, like most significant plans, the proposal’s journey was filled with unexpected twists.

Almost there…

    A few days after our initial exchange, Peter and I met in person at the hotel to finalize the details. Though Peter’s excitement was palpable, I could tell he was feeling the weight of this once-in-a-lifetime event. Hotel El Convento had suggested reserving a spot at their partner property, Palacio Provincial, which boasts a rooftop with stunning views of Old San Juan’s historic skyline. We decided to scope out the location during Golden Hour to assess the lighting and angles, as any seasoned Puerto Rico wedding photographer knows how crucial these elements are to capturing magic.

Inching closer…

   When we arrived, the rooftop’s charm was undeniable, yet something felt off to Peter. He couldn’t picture this as the backdrop for his grand gesture. Recognizing his hesitation, I suggested exploring other nearby locations to find the perfect spot. Together, we wandered through the cobblestone streets, considering picturesque alternatives until we stumbled upon La Rogativa. This outdoor plaza, adjacent to the Governor’s Mansion, offered stunning views and an intimate ambiance. It’s a favored spot for ceremonies and proposals alike. However, fate threw another curveball: a wedding ceremony was being set up there on the very day Peter planned to propose.

The joint disbelief.

     Undeterred, Peter made a last-minute decision to choose a small, tucked-away spot just a few feet from the original venue. As a Puerto Rico photographer familiar with the area, I instantly knew where he was referring to and began mentally planning how to work around its consistent backlighting. Challenges like these are what make surprise marriage proposals in Puerto Rico so thrilling to document—and rewarding when everything comes together.

On one knee…

     The day of the proposal was charged with emotion. Peter was visibly nervous, but after a few reassuring words and a reminder to savor the moment, he seemed to find his footing. Debora arrived hand-in-hand with her best friend, looking radiant in a white dress. Unbeknownst to her, she was mere moments away from one of the most significant events of her life. When Peter finally got down on one knee, Debora’s reaction was a mix of shock, joy, and humor—expressions so vivid and heartfelt that I couldn’t help but laugh along as I captured them.

She said yes!

     As Debora said “yes,” the moment unfolded like a scene from a movie. Her parents, who had been watching from a distance, rushed to embrace their daughter. Phones were pulled out, FaceTime calls were made, and tears flowed freely. It was a quintessential example of why surprise marriage proposals in Puerto Rico are so unforgettable: the blend of emotional authenticity and stunning scenery creates something truly magical.

Cheers to the future son-in-law.

     Once the initial excitement settled, I whisked Peter and Debora away for an intimate portrait session. There’s something special about capturing couples right after a proposal; the raw emotions and newfound glow are unparalleled. Debora was still shaking with excitement, making it a challenge to photograph her gorgeous engagement ring, but the candid moments we shared were priceless.

She still can’t believe it!

     As the sun dipped below the horizon, we regrouped with their family and friends for some celebratory portraits. The golden light painted the sky in hues of pink and orange, a perfect backdrop for the occasion. To add a modern twist, I used flash photography to create trendy, paparazzi-style shots that have become increasingly popular among couples. The result? A gallery of images that captured every ounce of love, joy, and excitement from that unforgettable evening.

In awe of reality.

     The day concluded back at Palacio Provincial’s rooftop, where Peter and Debora shared their happy news with loved ones. The weather was idyllic, and the atmosphere was electric with celebration. As a Puerto Rico wedding photographer, moments like these remind me why I love what I do: the opportunity to witness and document life’s most meaningful milestones.

Wholesome sunset.

     Peter and Debora’s proposal was a testament to the power of love and spontaneity. It’s a story I’ll cherish for years to come, and I wish them nothing but the best as they embark on this new chapter together. If you’re considering a surprise marriage proposal in Puerto Rico, know that the possibilities are endless, and the memories you create will be as vibrant and enduring as the island itself.

Epic.