There’s a moment in every wedding day when I know I’m witnessing something special. For Meredith and Gary, it came during the pleneros procession. The newlyweds dancing through the cobblestone streets of Old San Juan, the drums echoing off pastel-colored colonial walls, guests trailing behind in pure celebration mode. This La Rogativa wedding ceremony was my last of 2025, and it was the perfect way to close out my 17th year as a wedding photographer.

A Courtroom Love Story

Some couples meet on dating apps. Others through mutual friends. Meredith and Gary? They met when a fight broke out in a Massachusetts courtroom.

Meredith is a criminal attorney. Gary is a court officer. One day, while Meredith was prosecuting a case, chaos erupted in the courtroom. Gary, in charge of security, had to physically move her out of harm’s way. As icebreakers go, it’s unconventional, but it worked. They started talking after that incident, and the rest is history.

When I first met them over Zoom and learned about their story, I knew this couple would bring energy, humor, and heart to their wedding day. I wasn’t wrong.

 

Why La Rogativa for a Wedding Ceremony

Gary is a self-proclaimed history nerd, and Old San Juan was calling his name. The 500-year-old architecture, the stories embedded in every blue cobblestone, the fortress walls overlooking San Juan Bay. This is a place where history feels alive.

Plaza de la Rogativa sits tucked behind La Fortaleza, the governor’s mansion, with sweeping views of the bay and the city walls. The bronze statue at its center commemorates a legendary 1797 event: a women-led religious procession that inadvertently scared off British invaders who mistook their torches for Spanish military reinforcements.

It’s a place of courage, faith, and a little bit of magic. Fitting for a wedding ceremony.

For couples considering a La Rogativa wedding, here’s what makes it exceptional:

The views. You’re exchanging vows with San Juan Bay as your backdrop, the historic city walls framing the scene, and (if you time it right) golden hour light spilling across everything.

The intimacy. This isn’t a massive venue. It’s a plaza, open air, surrounded by history, perfect for ceremonies where you want your guests close.

The walkability. La Rogativa is a short stroll from Hotel El Convento, making the transition from ceremony to reception seamless. Add pleneros, and that walk becomes a full-on celebration.

 

Getting Ready at Hotel El Convento

The day started in the Casals Suite at Hotel El Convento, the 360-year-old former Carmelite convent that’s become one of Old San Juan’s most iconic wedding venues.

Meredith’s look was elegant and modern: a white strapless gown with a high slit, a flowing veil, an all-white orchid bouquet with cascading greenery, and my favorite detail, cobalt blue heels that popped against the historic architecture.

Gary wore a tan linen suit with brown leather shoes. Lightweight, but polished, exactly right for a humid December wedding in Puerto Rico.

We did their first look indoors at El Convento, taking advantage of the hotel’s beautiful arched corridors and golden-yellow walls while the midday sun was still too harsh for outdoor portraits. The way Gary looked at Meredith when she tapped him on the shoulder? That’s the stuff I live for.

The Ceremony at Plaza de la Rogativa

There had been weather suspense all day. That classic Puerto Rico dance where clouds threaten but often deliver nothing but drama. By 4pm, when guests gathered at La Rogativa in their colorful cocktail attire, the sky had softened into perfect ceremony light.

White ghost chairs lined a simple aisle. The bronze statues of the Rogativa women stood witness. And Meredith walked toward Gary with the kind of joy that’s impossible to fake.

The ceremony was emotional, personal, and punctuated by the best kind of ending: Gary dipping Meredith into a kiss while their guests erupted in applause. That image, her veil flowing, his arms steady, everyone on their feet, and surprisingly, no phones in sight, is an instant-favorite of mine!

Pleneros Through Old San Juan

If you’re planning a wedding in Puerto Rico and haven’t considered hiring pleneros, let me make the case for it.

Pleneros led Meredith, Gary, and their guests through the narrow streets of Old San Juan after the ceremony. The drums, the energy, the way strangers stopped to smile and wave. It transforms the transition from ceremony to reception into a celebration of its own.

We captured portraits along the way: the couple laughing against pastel colonial facades, the pleneros in the background, the blue cobblestones underfoot. These are the images that feel most alive, most Puerto Rico.

Reception at Salón Campeche

The party moved to Salón Campeche at Hotel El Convento, a room that needs no introduction if you’ve seen it. The original chapel of the Carmelite convent, it features 50-foot vaulted ceilings, black and white marble checkered floors, wrought iron chandeliers, and arched windows that glow as the sun sets.

STEM Events styled the reception with tropical elegance: palm fronds, orchids, candles of varying heights, cane-back chairs, and pops of pink and green against the neutral palette. The long banquet tables created an intimate feel despite the room's grand scale.

One of my favorite shots from the day is the overhead view of Meredith and Gary sharing a quiet moment on that checkered floor, surrounded by the tables set for their guests. Romance framed by celebration.

This was one of those weddings where I genuinely had to remind myself to keep shooting because I was having so much fun. The couple’s guests, flying in from Boston, New York, Texas, and even London, brought the energy. Meredith and Gary matched it.

Why Destination Weddings in Puerto Rico Work

Meredith and Gary came from north of Boston. Many of their guests had never been to Puerto Rico. But from the moment everyone arrived, there was this sense of adventure, of being somewhere special together.

That’s the magic of a Puerto Rico destination wedding. No passports required for US guests, but it feels like you’ve traveled somewhere extraordinary. The history of Old San Juan, the warmth of the people, the colors, the music, and the food. It all combines into an experience that goes beyond a single day.

Meredith and Gary, thank you for trusting me with your wedding day. Working with you both felt effortless. Your kindness, your energy, and your obvious love for each other made every moment a joy to capture. I meant what I said: a little bit of each of my couples stays with me forever, and you two are no exception.

xo,

Cami