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.

Angela & Nick: A Surprise Marriage Proposal in Vieques, Puerto Rico

Punta Arenas Beach, Vieques, Puerto Rico

     As a destination wedding photographer in Puerto Rico, I’ve captured countless love stories, but this one took me somewhere entirely new—Vieques, a small island municipality off the east coast of Puerto Rico. It was actually my first time visiting, and the reason for doing so was because Nick, a gentleman from Virginia, reached out to me wanting to propose to his longtime girlfriend, Angela.

     Nick contacted me via my website and we hit it off from the start. He stated that they matched on Hinge just over a year ago and met for dinner the very next night. They both felt it—one of those rare “this is my person” moments—before the appetizers even arrived. Since that first date, everything has been equal parts effortless and magical, from spontaneous road trips to quiet Sunday breakfasts.

The preface

     Nick was adamant about proposing outside of the mainland, so this meant booking flights, renting a Jeep, and possibly staying overnight at an Airbnb. After logistics were taken care of on my end, I let Nick know and we were off to the races.

     As I arrive to Isla Grande Airport, Angela and Nick sit down in front of me at the gate and I had to contain my laughter because he was literally not supposed to be there; humorously, I later find out he missed his first flight out, thus forcing him to catch the next one. As if that wasn't funny enough, all three of us were the only passengers in the same flight to Vieques.

The magical moment

     Nick tried to make small talk with me during the flight and asked questions as if we didn't know who we were because we couldn't blow our cover in front of Angela.

     When we arrived at the airport in Vieques, I see Nick heading to the bathroom and I use it as an opportunity for a quick, covert conversation in private. As we're both washing our hands, I take a few minutes to give him a refresher course of what's going to happen later that afternoon at Punta Arenas Beach, the venue Nick had set his sights on.

Sweet bliss

     Defusing the anxiety bomb in my client's chest is always a great thing to do because it's a very nerve-racking moment for your proposers. I also take advantage of the moment to tell Nick I'll be checking into Hix Island House, my chosen Airbnb spot, renting a Jeep Wrangler at Avis Rent-A-Car, and heading to Punta Arenas early so that I can scout the best locations on the beach.

     As fate would have it, we took a courtesy car to the car rental location and fine-tuned the details. We'd be seeing each other again in a matter of six hours or so, therefore I grabbed snacks at the nearby supermarket and went to check-in at my Airbnb destination.

The sandy knee

     I was told by the car rental place that Punta Arenas is infamous for mosquitoes and gnats during Golden Hour, so I made sure to buy some insect repellant; after showering at my Airbnb, I lathered myself in two coats so that flying insects would not be a distraction throughout our event. Little did I know this would prove to be futile.

     I get to Punta Arenas Beach in Vieques at least an hour before our scheduled marriage proposal in Puerto Rico. I kindly ask Nick if he's alone so that I can FaceTime him and show him the two areas within his preferred beach that we can shoot in. After contemplating both for a few minutes, we decide on a more secluded part of the beach where only a couple could be seen embracing in the water and enjoying each other's company.

Wholesome

     I interrupted them to tell them I was a destination wedding photographer in Puerto Rico who would shortly be documenting a surprise marriage proposal, and they became quite excited. I had an ulterior motive as well: since Nick had requested a video clip of the actual proposal, I needed a place to hide my tripod and camera discreetly so that Angela didn't suspect a thing if she were to see it out of the corner of her eye.

     I asked the couple if I could set the rig between their two beach chairs with one of their towels over it, and they were nice enough to allow it.

Two peas in a black and white pod

     Shot number one was in place. The second vantage point was my new GoPro Hero 13 Black strapped to my left shoulder as a POV/behind-the-scenes angle. Nothing beats being able to see an event through my eyes, and there's no better way to experience it than to have your photographer document the process as it happens from his/her eyes.

     Finally, my Canon R6 Mark II had my RF 100mm IS L USM lens on it so that I could be discreet from a distance and take that ever-so-important shot of the preface of the couple as well as Nick down on one knee.

Majestic

     As the moment arrived, I was in position making sure that I wasn't blocking the static shot from the other camera recording video. Angela was over the moon and gave Nick a resounding yes. I know this not only because of her reaction, but because I strategically placed flowers with a microphone hidden in the stems to capture audio as best as I could.

     After a minute or so of allowing the couple to wipe their tears and fix their hair, I approached Angela and Nick and she couldn't believe it! She blurted out: "OMG, it's YOU!" referring to having seen me throughout the course of the day and hiding in plain sight. All three of us got a laugh, and I proceeded to fill Angela in on what had transpired in secret in order for all of this to happen. Her jaw was on the floor in terms of logistics that needed to take place, and Nick and I high-fived each other to seal the deal on an epic adventure.

Golden Hour at Punta Arenas Beach in Vieques, Puerto Rico

     Since we were burning daylight, we took advantage of the gorgeous Golden Hour to enjoy an engagement photoshoot with what sun we had left. This is the part where the gnats and mosquitoes started to play a role. Since I was breathing heavy and sweaty from all of the running around, I was an easy target and they definitely didn't let me off the hook. I constantly had around ten of them in my face the entire time and made it very difficult to get shots in; my couple wasn't having too much fun either. As much as I hate to admit this: I must’ve inhaled about five gnats and washed them down with some Pellegrino mineral water shortly thereafter. 

     Angela and Nick could barely hold still for more than three seconds before having to swat bugs from their face and bodies. We made it happen nonetheless, and I even whipped out some flash photography towards the end, but things became so miserable that we mutually agreed to end the session because it became unbearable to be there. We were forewarned about the insect situation, but when the client knows what they want, it's my goal as a destination wedding photographer in Puerto Rico to oblige.

Perfection personified

    A few days later, I sent Angela and Nick their pictures along with their lightly edited video, and they're over the moon. My first time in Vieques, Puerto Rico was an absolute success, and I cannot wait to go back!

     Planning your own Puerto Rico proposal or engagement session? Whether it's Vieques, Old San Juan, or a hidden beach spot, I’d love to help bring your vision to life.

     Contact me today and let's make it happen.