Puerto Rico Engagement Photos in Old San Juan

Vicki was on the hunt for a documentary-style photographer who also shot film—someone who wasn’t afraid to embrace the grainy magic. During our consult, she casually dropped, “We’re going to Puerto Rico in two weeks… would it be insane if you met us there for engagement photos?” Cue my immediate: “Absolutely not.” Because when the vibes are right, and the flights are available, you say yes. The minute they officially booked me for their October wedding, I was on Google Flights, making it happen. Puerto Rico engagement photos? Twist my arm.

Touching Down in Puerto Rico for Some Film Engagement Photos

The second my plane touched down in San Juan, I knew two things:

1. I was so pumped to photograph Vicki and Lazaro in one of the most vibrant and romantic cities.
2. My Midwestern body was not ready for the kind of heat and humidity Puerto Rico was serving. (Truly, I melted. Like a popsicle on a sidewalk.)

But we embraced it all, even with the sweat and a few surprise sprinkles of rain. The kind of weather that makes you adapt on the fly actually gave us some of the dreamiest, most intimate moments. And honestly, that’s what documentary-style photography is all about—capturing whatever unfolds beautifully and honestly.

Vicki and Lazaro met while living in NYC, and their connection is effortless, like finishing each other’s sentences kind of energy. Shooting in Old San Juan on film, with its pastel walls, sun-drenched corners, and perfectly weathered cobblestone, was a dream. The colors, texture, and mood brought everything to life.

Thinking of Puerto Rico Engagement Photos? Here’s What You Need to Know

We wandered through Old San Juan until sunset, weaving through cobblestone alleys. Even with the city’s evening buzz, we had no trouble finding peaceful little spots to soak in the moment.

We laughed (and sweated) our way through the heat. But once we got down to the beach, it was like a little break for us as these two played around in the water.

Here are a few tips if you’re dreaming up your own Puerto Rico engagement photos:

• It’s hot—like a tropical vacation hot. Opt for lightweight, breathable fabrics that won’t make you sweat immediately (linen is a great choice).
• Comfy shoes are a must. You’ll be doing a lot of walking, and the cobblestones are no joke—cute heels might not make it far.
• Be flexible with the weather. A quick rain shower isn’t uncommon, but it usually passes quickly, and sometimes, it adds a little extra magic.
• Crowds aren’t a dealbreaker. Even during the evening rush, we found plenty of beautiful, people-free spots for photos. You just have to know where to look!

Puerto Rico Photographer | Maddi Waldo Photo

Vicki and Lazaro have a full October wedding day in the works, and if it’s anything like this session, it’s going to be amazing. I already can’t wait! I’m genuinely honored that they trusted me with this tropical chapter of their story, and I’m even more excited to keep telling it as it unfolds.

Want to see another vibe? Check out these dreamy sunrise engagement photos on the Minnesota North Shore. Are you thinking about planning your own destination engagement session or wedding? Let’s chat—I’d love to help you dream it up.