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 Romantic Old San Juan Couples Session | Destination Photography in Puerto Rico

Kaitlyn & Tanner

     When it comes to couples photography in Puerto Rico, few places offer the breathtaking scenery and rich cultural charm of Old San Juan. Recently, I had the pleasure of photographing Kaitlyn and Tanner, a young couple visiting from Mississippi, who wanted a session capturing the historic beauty of Old San Juan during golden hour. As a destination wedding photographer in Puerto Rico, I always aim to create unforgettable experiences for my couples, and this session was no exception.

Why Old San Juan is a Dream Location for Couples Photography

Green framing.

     Old San Juan is one of the most iconic photography locations in Puerto Rico, known for its cobblestone streets, colorful Spanish colonial architecture, and historic landmarks. Many couples choose this vibrant district for their engagement photos, anniversary sessions, and even elopements. The magic of golden hour photography in Old San Juan enhances the city's beauty, providing warm, glowing light that makes every photo look timeless.

     Kaitlyn and Tanner were staying at La Concha Renaissance Hotel, one of the best wedding venues in Puerto Rico. Although they loved their resort, they knew that Old San Juan's eclectic environment and vibrant energy would provide the perfect setting for their session.

Starting the Session at El Convento Hotel

Sucker for geometry.

     We began our session near Hotel El Convento, widely regarded as one of the most prestigious wedding venues in Puerto Rico. This luxurious boutique hotel, formerly a nun’s convent, features elegant Spanish architecture, lush courtyards, and romantic archways, making it a favorite for destination weddings in Puerto Rico. I hosted a wedding there at the end of 2024, and it remains one of my most memorable experiences as a Puerto Rico wedding photographer.

Exploring the Streets of Old San Juan

An Old San Juan classic.

     From El Convento Hotel, we walked down Caleta de las Monjas, a historic and picturesque street that offers charming backdrops for engagement and couples photography in Puerto Rico. The pastel-colored buildings, ornate balconies, and classic blue cobblestones create an intimate and nostalgic setting.

     We then made our way to La Rogativa, a well-known sculpture near the Governor’s Mansion in Old San Juan. Many destination wedding ceremonies take place here due to its stunning views and historical significance. Capturing romantic moments against this breathtaking backdrop made for a truly special part of the session.

Sunset Portraits at El Morro

What a way to end it.

     No couples session in Old San Juan is complete without visiting El Morro, Puerto Rico’s most famous landmark. The sprawling 16th-century fortress is a favorite among destination wedding photographers because of its dramatic ocean views and open fields that allow for stunning, natural-light portraits. As the sun began to set, I used my Godox AD100 Pro flash with an orange gel, mimicking the last rays of sunlight to create a dreamy, cinematic effect. This ended up being my favorite shot of the session, and Kaitlyn and Tanner were absolutely in love with the final images.

Book Your Old San Juan Couples or Engagement Session

     If you’re searching for a luxury destination wedding photographer in Puerto Rico or looking to capture romantic moments with your partner, Old San Juan is the perfect place. Whether you're newly engaged, celebrating an anniversary, or simply want beautiful photos together, I’d love to create something unforgettable for you.

     For inquiries about engagement sessions in Old San Juan, wedding photography in Puerto Rico, or destination wedding packages, reach out today. Let’s turn your love story into timeless imagery!

A Romantic Couple's Photoshoot in Old San Juan

Sai and Uha

     Puerto Rico is a magical place for couples looking to celebrate their love, and as a wedding photographer in Puerto Rico, it’s always a delight to meet people like Sai and Uha, whose story added even more charm to my portfolio. The couple, visiting the island for just a few days, reached out to me last minute to capture their time in paradise. Without hesitation, we scheduled their session in the heart of Old San Juan, where the vibrant streets and historic backdrops provide endless opportunities for breathtaking photography.

It’s all about the details…

     We began the session at the picturesque El Convento Hotel, a historic venue rich in color and texture. Sai looked incredibly sharp in a sleek black suit, which paired beautifully with Uha’s dazzling red gown adorned with sparkles. Adding to their elegant look was a petite bouquet of three roses that became a simple yet striking prop throughout the shoot. Beneath the hotel’s canopy, the interplay of light and shadows created a dramatic ambiance that made their portraits pop.

A rose for a rose.

     From El Convento, we ventured to Caleta de Las Monjas, a cobblestone street steeped in history. The narrow alley, framed by colorful walls and wrought iron details, was the perfect place to create intimate images. As we moved through the street, Sai and Uha’s chemistry shone through, making my job as a photographer both easy and deeply rewarding.

Met at work; almost two years of marriage.

     Their request to include El Morro, Puerto Rico’s iconic fortress, was no surprise. However, I encouraged us to take a detour to capture moments along the way. Walking the streets of Old San Juan offered countless candid opportunities, from gentle laughs shared over the roses to quiet moments with the ocean breeze in the background. These spontaneous shots added a layer of authenticity to their gallery, showcasing their genuine connection amidst the vibrancy of Puerto Rico.

Au naturelle…

     As a Puerto Rico wedding photographer, I pride myself on adapting to my clients’ visions while weaving in my creative touch. At El Morro, I embraced the challenge of balancing Sai and Uha’s desire for classic fortress shots with my inclination for fresh perspectives. Using the sweeping landscapes and dramatic skies as our backdrop, we captured timeless images that truly encapsulated the essence of their bond.

The simpler, the better…

     The bouquet of roses became more than a prop—it was a symbol of the simplicity and beauty of their love. We used it to highlight certain poses, such as Sai gently holding the flowers while Uha smiled at him, and even as a playful element during candid moments. The red roses paired effortlessly with Uha’s dress, creating a striking color palette against the soft tones of the historic walls.

VOGUE-ing

     Old San Juan’s charm lies not just in its landmarks but also in its quiet corners. A secluded bench, a rustic doorway, or the reflection of light on cobblestones can transform a photograph into something extraordinary. Sai and Uha’s session reminded me why I love working as a photographer in this enchanting city; every corner tells a story waiting to be captured.

Make it interesting…

     When we finally reached El Morro, the expansive view was worth the walk. Against the fortress’s iconic stone walls and lush green grounds, Sai and Uha’s love took center stage. The light was perfect, casting a soft glow that enhanced the mood of their final portraits. It was the perfect conclusion to a shoot that blended elegance, spontaneity, and adventure.

Have fun with each other…

     Being a wedding photographer in Puerto Rico is more than just documenting special moments; it’s about connecting with people and helping them preserve their memories in meaningful ways. Sai and Uha’s session is a testament to the beauty of love and the magic of Puerto Rico as a destination.

Elegance.

     To couples considering Puerto Rico for your photoshoot, this island offers endless possibilities. Whether it’s Old San Juan, the beaches of Vieques, or the lush El Yunque rainforest, the options are as vibrant as the love stories I’m privileged to capture. If you’re looking for Puerto Rico wedding photographers who blend creativity with heartfelt storytelling, don’t hesitate to reach out. Let’s make your moments unforgettable.

The must-have in Old San Juan

Strike a pose.

Making memories…

Make sure you always dip her.

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.