Mackenzie & Matthew’s Old San Juan Wedding at Hotel El Convento and Plaza de la Rogativa

There’s a reason Old San Juan weddings feel different. The city itself becomes part of the story the cobblestone streets, pastel walls, centuries-old cathedrals, and Caribbean light wrapping everything in romance. For Mackenzie and Matthew, their celebration wasn’t just a wedding; it was the kind of experience couples dream of when they imagine saying yes in Puerto Rico.

As a wedding photographer, I’ve captured dozens of celebrations in Old San Juan, and this one represents exactly what I call “the perfect Old San Juan wedding experience.”

Getting Ready at Hotel El Convento

Why El Convento is a favorite for destination weddings

Hotel El Convento is a favorite for destination couples for good reason. It’s not only an iconic boutique hotel (a 17th-century convent turned luxury space), but also a venue that eliminates one of the biggest planning stressors: logistics.

By getting ready, doing their first look, and hosting their reception all within the hotel, Mackenzie and Matthew kept everything centralized. Their bridal suite overlooked the streets of Old San Juan, the architecture framed every candid moment beautifully, and the staff made the day flow seamlessly.

Planning Tip: If you want your day to feel effortless, choose a venue like El Convento that can host multiple parts of the wedding in one location. It saves time, avoids transportation headaches, and keeps the vibe calm and intentional.

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First Look in the Salon Martorell

The Salon Martorell is one of the hidden treasures inside El Convento — a historic room with dramatic arches, ornate artwork, and incredible natural light. It gave Mackenzie and Matthew a private, cinematic setting for their first look, away from the bustle of the streets.

For couples wondering where to have a first look in Old San Juan: this is one of the most atmospheric indoor spots. It balances history and intimacy, giving you photographs that look like fine art.

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Ceremony at Plaza de la Rogativa

An intimate, cinematic setting in the heart of Old San Juan

Just a short walk from El Convento sits the Plaza de la Rogativa. Overlooking San Juan Bay, with statues and stone walls framing the view, it’s one of the most striking ceremony locations in Puerto Rico. Mackenzie and Matthew’s guests were in awe — the ocean breeze, the golden Caribbean light, the sounds of Old San Juan in the distance.

Planning Tip: Because Plaza de la Rogativa is a public space, you’ll need a permit and coordination with your planner to secure it. Many couples don’t realize this until late in planning — booking an experienced planner (and vendors who know the ins and outs) makes the process smooth.

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Reception in El Convento’s Courtyard

Back at El Convento, the courtyard transformed into a celebration under twinkling lights. Guests danced, toasted, and filled the night with laughter while the colonial arches surrounded them. For couples deciding between a resort ballroom and an Old San Juan venue: this is the difference. It’s elegant, romantic, and undeniably Puerto Rican — the kind of setting that makes guests say, “This is unforgettable.”

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Why Old San Juan Is Perfect for Weddings

Couples often ask me: “Is Old San Juan right for my wedding?” Here’s why Mackenzie and Matthew’s day shows the answer is yes:

• Proximity: Ceremony and reception locations are within walking distance. Guests won’t need to shuttle back and forth.
• Scenery: Every corner is photo-ready — cobblestones, balconies, plazas, colorful walls. Your portraits don’t need staging; the city itself tells the story.
• Atmosphere: Old San Juan balances elegance with vibrancy. You get romance, history, and culture all woven together.
• Guest Experience: For destination weddings, your guests get more than a weekend celebration — they get to explore one of the Caribbean’s most historic cities.

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Making Old San Juan Stress-Free

While the charm is unmatched, there are details worth preparing for:

• Weather: Warm afternoons and unexpected showers are common. Plan ceremonies closer to golden hour and have umbrellas ready.
• Crowds: Old San Juan is popular with tourists and cruise ships. Work with vendors who know how to time things around the flow of the city.
• Permits: If you want to marry in plazas, your planner or photographer can guide you through what’s required.

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Final Thoughts

Mackenzie and Matthew’s wedding captured everything Old San Juan has to offer: history, romance, and effortless elegance. From their first look in the Salon Martorell to vows overlooking the bay, every moment felt cinematic.

If you’re dreaming of a destination wedding that blends culture, beauty, and intimacy, Old San Juan is more than a backdrop — it’s a character in your love story.

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