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.

Decanter Hotel & Old San Juan: The Perfect Backdrop for Bryan & Mary Luz

Ladies and gentlemen, the future bride and groom…

The Engagement Session in Puerto Rico

Bryan and Mary Luz met during the pandemic. Like many couples, they resorted to each other in difficult times which is a great starting point a wonderful friendship. Finding solace in a partner in the face of adversity can lay the foundation for an incredible romantic partnership. They hail from Connecticut but wanted to escape the continental U.S. to get married in Puerto Rico at La Concha Hotel in Condado, a venue that, as a professional photographer, I’m extremely familiar with. I shot one of my most complete weddings there last year with Carlos & Denise and memorized all of the great spots for pictures. I trust I can achieve the same results with these two lovebirds.

They flew in recently to Puerto Rico to secure the venue and we figured it would be a great opportunity to shoot their engagement session in Old San Juan, a city that is eclectic in nature and as colorful as they come. As a wedding photographer in Puerto Rico, this happens to be one of my most frequented stops along my journey because the feeling Old San Juan provides is just otherworldly. You get the classic Spanish vibes mixed with modern nooks and crannies making it the perfect backdrop for an engagement session as a prequel to a wedding. Once the venue was secured, we proceeded to meet up at the Decanter Hotel across the street from El Convento, also a popular wedding venue in Puerto Rico.

What a tender moment…

Our first order of business was getting to meet in person. Believe it or not, we hadn’t even met virtually beforehand and I was looking forward to doing so. After getting to Old San Juan rather early for some grub, I asked Mary Luz if she’d be OK with me heading into the Decanter Hotel and taking some pictures of them getting ready together. Not only do I think it’s super cute but it just so happens to be one of my favorite parts of being a destination wedding photographer in Puerto Rico. Intimacy and romance is a combination I enjoy photographing and, being the hopeless romantic I am, it’s safe to say that it’s very near and dear to my heart seeing my couples interact with each other in an organic and authentic manner.

Not only did Mary Luz think it was a great idea but I showed up early since I tell all of my couples that, as a professional photographer, I’m always “annoyingly punctual” anywhere I’m requested in Puerto Rico. One of my reasons for doing so, regardless if it’s a wedding or elopement, is due to the fact that I enjoy a stress-free environment, something I take great pride in providing for all of my clients. When the doorman let me upstairs, I quickly made my way to the elevator and in a matter of minutes I was knocking on their door and shaking hands. Immediately I could feel a sense of togetherness and warmth and their vibe was definitely down-to-Earth.

How does this go again…?

As soon as we were done exchanging pleasantries, I went immediately to scout the room that they had rented and, although it was quite cozy, it did have a lot of natural light allowing me to capture genuine moments of them getting ready. Admittedly, Mary Luz was still wondering what dress to go with and, after comparing her original choice to a more yellow, sundress vibe we decided to go with a classic white sleeveless number. Bryan, on the other hand, opted to leave his suit jacket behind and stick to just a tie seeing as how it’s as hot as it gets in Puerto Rico.

Once I felt as though we had taken enough pictures to put together a solid prequel to their outing, we then proceeded to exit the premises but not before making a few pit stops along the way. First, I noticed the nice archways perfect for an engagement photography session. I maintained my distance as much as I could and snapped a few portraits of them for a safe distance (although I could hear them whispering sweet nothings into each other’s ears). We then took the elevator downstairs where we stumbled across the lobby garden I had seen on the way up; I knew that coming down I’d want to sit them there, specially when I saw we had it all to ourselves for a few minutes. There’s nothing quite like an uninterrupted session for an engagement photographer in Puerto Rico.

“Hi…hi back

I was actually surprised by the fact that the Decanter Hotel happens to be a solid choice for an engagement session in Puerto Rico. Their staff was welcoming, the rooms were easy to find, it looked like they had all of the amenities one might need and the overall ambiance of the place was extremely versatile during my visit. I wholeheartedly recommend taking a look at this and considering incorporating this as a wedding venue in Puerto Rico to some extent because it appears you have everything all in one place and could be a wonderful precursor as part of the portfolio to a wedding photographer in Old San Juan.

As fate would have it we made our way out into the hot streets of the city where we met up with Bryan, the Swiss-Army knife of my photography team and my chosen assistant for the day. I figured it’d be an excellent way to test my flash photography skillset by having him carry a monopod pole all session long with a Godox AD100 strobe at the end of it. Paired with my new Godox X3 trigger it was an absolutely breeze to shoot Bryan and Mary Luz and let them know what would be taking place for the foreseeable future. Dimming down the background a bit and then shining the light on this lovely couple made for a wonderful engagement session in Old San Juan that I shall not soon forget.

“Lights, camera…LOVE!”

I feel like I certainly outdid myself as far as creative lighting is concerned. That’s why I love a great engagement session prior to the wedding day because it allows for that outside-the-box mentality that’s required and not allowed for the most part during the bride and groom session at a nuptials ceremony in Puerto Rico. By having an assistant like Bryan shadow us around, I was able to take a step back and shoot from the cuff while not thinking too much and forcing my back against the wall to think on my feet.

We actually ventured to spots I normally don’t visit like Casa Blanca (admittedly, we sneaked in before the venue was open and took some of my favorite shots in their lovely green areas). The sun was steadily setting and we knew we were burning daylight but at the same time it was the perfect opportunity to capitalize on a combination of artificial and natural light which captivated our eyes and made for an amazing end to my session as a Puerto Rico engagement photographer. I’ll leave you now with what I think are some of the best flash photography I’ve taken. Remember that if you’d like to get together with me, you can simply click here and send me a message so that we can perhaps talk about putting together an epic wedding photography memory in Puerto Rico. Thanks so much for reading along and I’ll see you in the next blog! -F

Walk with me…

“Oh, hi there…”

Cheers to us.