A Surprise Marriage Proposal in Culebra, Puerto Rico
Flamenco Beach, Puerto Rico
About two months ago, I received a message through my website from Jared, a thoughtful guy from Texas who had something big in the works. He and his longtime girlfriend, Ashley, were planning a trip to Puerto Rico—and he wanted to turn their vacation into something unforgettable: a surprise marriage proposal.
As a wedding and proposal photographer based here on the island, moments like these are a highlight of my work. But when the stakes rise to the level of flying to a separate island municipality to pull it off? That’s a double win for me. Documenting destination proposals is a privilege I never take lightly.
Choosing Culebra: Off the Beaten Path
The big moment at Flamenco Beach in Culebra, Puerto Rico
Jared was drawn to Culebra, a small, picturesque island just off the east coast of Puerto Rico known for its beaches and laid-back vibe. Accessible only by plane or ferry, it’s the kind of place where time slows down and nature steals the show. It’s also one of my favorite proposal spots when couples are looking for something unique and secluded.
We jumped on a few planning calls, going over everything from timing and wardrobe to signal issues and cues. Part of my service to Jared included arriving on the island early to scout potential proposal spots and send him options. I wanted everything to be seamless.
Scouting the Best Beaches (And Dealing with Sargassum)
Culebra, Puerto Rico
A few days before their arrival, I hopped on a small plane and began exploring Culebra by golf cart—yes, golf cart. It’s the local way of getting around if you’re not actually from there. The mission? To find a proposal location worthy of their story.
But there was one curveball: sargassum.
This seaweed-like algae had taken over almost every major beach. Flamenco Beach, often ranked as one of the top five beaches in the world, wasn’t spared. Neither were Zoni, Soldado, or Melones. Each one had its own beauty, but either the seaweed, rocky shorelines, or harsh lighting made them less than ideal.
Eventually, after several hours of exploring, Jared and I found a tucked-away spot on the far right end of Flamenco Beach. It was private, beautifully lit in the late afternoon, and the water was clear of sargassum. I flagged it as the winner and began preparing the logistics for our Golden Hour shoot.
An Unexpected Coffee Shop Encounter
She said yes at Flamenco Beach in Culebra, Puerto Rico
On the day of the proposal, I had a few hours to kill before our 6 p.m. meet-up. I stopped by a cozy café called Culebra Coffee, just walking distance from the ferry station. I ordered an avocado toast with hummus and started chatting with one of the employees, Anita.
As we made small talk, I mentioned I was a photographer in town to shoot a surprise proposal later that day. And then—in walks Jared and Ashley.
I gave Anita a quick wide-eyed look that screamed, “Don’t say anything!” She caught on immediately. Don and Randy, the other shop employees, were doing their best not to laugh. And there I was, sitting next to Ashley, trying to keep a straight face while she placed her order. It was a surreal moment. Jared and I texted each other from across the room, cracking up at how small the island really is.
Crossing Paths Again (and Again)
Epic sunsets at Flamenco Beach in Culebra, Puerto Rico
After brunch, I resumed scouting. I gave Melones another look, but its rocky terrain made it a no-go for dropping to one knee. Zoni had poor lighting. Soldado? More sargassum. Flamenco still stood as the best option.
Meanwhile, Jared and Ashley were exploring the island on their own golf cart—and we kept accidentally running into each other. We passed several times on the road. Ashley must’ve thought I was some kind of creeper. Little did she know I was actually her photographer, waiting for the big moment.
Showtime at Flamenco Beach
Majestic photoshoot at Flamenco Beach in Culebra, Puerto Rico
We locked in our plan: Golden Hour at Flamenco.
I got there early and approached a few nearby beachgoers—a Spanish family and an Italian couple—asking kindly if they could move slightly out of the frame. They were incredibly gracious, and we ended up chatting. (I’m currently learning Italian, so it was a fun exchange.) I snapped a photo of the chosen proposal spot and sent it to Jared. The only problem? My phone had no signal.
I had to sprint all the way back to the main entrance of Flamenco Beach just to get a single bar of reception. After a three-minute struggle, the photo finally went through. Jared now knew exactly where to go. I raced back to my hiding spot in the foliage, positioned my camera, and waited.
The Proposal
The light was amazing at Flamenco Beach in Culebra, Puerto Rico
Moments later, I saw them approaching. I had a small window through the leaves where I could shoot discreetly. The light was perfect—the sun low, golden, and soft.
At first, Jared stood in the wrong area, blocking the view. I ducked down and turned around so Ashley wouldn’t see me, then repositioned. The Italian couple nearby acted like secret agents, letting me know in Italian when she wasn’t looking so I could pop back up and keep shooting.
Finally, Jared walked to the exact spot. He stood with Ashley for a moment, speaking from the heart. Then came our non-verbal cue: he turned his baseball cap backward—our secret signal that the proposal was about to happen.
The only challenge? He was so in the moment that he unknowingly had his back turned to me. I had to adjust quickly, scooting left and right to catch every angle as he dropped to one knee. She said yes.
After the Yes
Black and white hits different at Culebra, Puerto Rico
Once the excitement settled, I introduced myself. Ashley’s eyes widened in recognition. “Wait—you’re the guy from the coffee shop!” she laughed. And the golf cart sightings? Everything suddenly made sense.
I wasn’t a creeper. I was her Puerto Rico proposal photographer, doing his best to stay incognito.
As the sun began to set behind the island’s hills, I pulled out my Godox V100 flash and added a CTO gel to warm the scene. I lit them softly from below and we got creative with sunset portraits by the water. The sky was absolutely stunning—one of the most vibrant I’ve ever seen.
The Wrap-Up
Sunset at Flamenco Beach in Culebra, Puerto Rico
This proposal had everything: surprises, serendipity, scenic challenges, and just the right amount of chaos. And in the end, it couldn’t have unfolded more beautifully.
Jared and Ashley, thank you for trusting me with such an intimate moment. It was an honor to document the start of this new chapter in Culebra. I wish you a lifetime of love, adventure, and spontaneous coffee shop run-ins.
