A Puerto Rico Proposal Story: How We Turned Hurricane Erin’s Aftermath Into a Dream Engagement

The proposal that almost didn’t happen.

     When Cesar first reached out to me through my website two months ago, he was searching for a proposal photographer in Puerto Rico who could capture one of the most important moments of his life: asking his longtime girlfriend, Sondrea, to marry him. Like I do with all my clients, I suggested a quick FaceTime call so we could break the ice, talk through ideas, and align on his vision for the big day.

     Cesar knew he wanted a Puerto Rico proposal on the west coast, preferably at a beach in Rincón, one of the island’s most romantic and picturesque destinations. Together, we narrowed it down to Domes Beach, a favorite among surfers, but also perfect for proposals since most people stay in the water, leaving the sandy shore quiet and intimate.

Hurricane Erin Changes Everything

Legend has it Sondrea is still processing what happened.

     The day before Cesar’s planned proposal, Hurricane Erin passed just north of Puerto Rico. The storm left its mark across Rincón: sargassum lined the coast, the waves were rough, and the once turquoise waters had turned an unappealing brown. I scouted Domes Beach early that morning and quickly realized it wasn’t suitable for a proposal. I also checked Los Almendros Beach, another possible option, but conditions there were even worse.

     At that moment, I faced a decision: postpone the proposal or go above and beyond to find a new spot—on the very same day. For me, client service always comes first. Postponement wasn’t an option.

Scouting for the Perfect Proposal Location

Drama everywhere.

     I drove an hour to Aguadilla to check out Surfer’s Beach, a location another client had mentioned. Unfortunately, it too was covered in debris. Time was running out, and I needed to find a beautiful and private location fast.

     That’s when I remembered Punta Borinquen Beach, a hidden gem my father used to take me to when I was a child. Tucked away behind a golf course and accessible only by crossing a small wooden bridge, the beach revealed itself as a breathtaking, secluded paradise. Clean sand, blue water, and an untouched cliffside backdrop—it was everything a Puerto Rico proposal planner dreams of.

     I quickly filmed a short video and sent it to Cesar. Within seconds, he agreed to drive the extra hour. Just like me, he fell in love with the spot instantly.

The Proposal Setup

You can’t make this up.

     Cesar had arranged for a violinist and his cousin to help with decorations. While the musician was ready and waiting, his cousin accidentally set up on the opposite side of the bridge from where I had recommended. With daylight fading fast, we scrambled to move everything to the better location. By the time we finished, it was already 6:40 p.m.—forty minutes later than planned.

     That left us with only about twenty minutes of light for photos. But as a proposal photographer in Puerto Rico, I wasn’t going to let logistics ruin the moment. I worked quickly and captured every angle of the proposal, including romantic portraits of the couple afterward.

The Big Moment

Sweet embrace.

     Despite the last-minute challenges, the proposal was magical. With live violin music filling the air, Cesar dropped to one knee as the ocean sparkled in the background. Sondrea’s reaction was pure joy, and she later told us how grateful she was that we had gone the extra mile to make the moment so special.

     As the sun dipped below the horizon, I pulled out my flash to capture creative twilight shots, with a soft blue hue behind them. The images turned out ethereal, and Cesar and Sondrea now have a gallery filled with once-in-a-lifetime memories.

Why Hiring a Proposal Photographer in Puerto Rico Matters

All smiles that day.

     Proposals don’t always go exactly as planned. Weather, logistics, and last-minute changes can throw curveballs, but having an experienced Puerto Rico proposal photographer makes all the difference. Beyond just taking pictures, my role often feels like that of a Puerto Rico proposal planner—scouting locations, troubleshooting problems, and ensuring everything aligns perfectly for that once-in-a-lifetime moment.

     If you’re considering a Puerto Rico proposal, whether in Rincón, Aguadilla, San Juan, or elsewhere on the island, choosing the right photographer is essential. Not only will you walk away with beautiful images, but you’ll also have someone in your corner making sure the entire experience feels effortless and unforgettable.

Final Thoughts

It hasn’t hit her yet.

     Cesar and Sondrea’s engagement is one I’ll never forget. From hurricanes to last-minute location switches, it was the most challenging proposal I’ve photographed—but also one of the most rewarding. The pictures reflect not just their love story, but the resilience and dedication that went into making it happen.

If you’re ready to plan your own Puerto Rico proposal photography experience, I’d be honored to capture it for you.

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.

A Surprise Marriage Proposal at the St. Regis Bahía Beach Resort, Puerto Rico

The pinnacle moment

     When Jean first reached out to me via Facebook, I didn’t realize I was about to document one of the most romantic proposals I’ve ever witnessed. He had stumbled across my public profile and messaged me with a heartfelt mission: he wanted to propose to his girlfriend, Steffane, while visiting Puerto Rico.

     Their love story was special. Jean and Steffane had first met in high school, where they shared a scholarly, friendly bond—but life had other plans. Years passed and it wasn’t until the height of the COVID-19 pandemic that fate brought them back together. Amid a global crisis, their connection rekindled and evolved into a deep, lasting love.

A happiness collage

     Jean told me he would be attending a wedding on July 5th at the stunning Hacienda Siesta Alegre in Puerto Rico. Inspired by the romance of the event, he thought it would be perfect to propose the following day, capitalizing on the lingering emotions from the wedding to create their own beginning. His vision? A surprise proposal at the luxurious St. Regis Bahía Beach Resort in Río Grande.

     He texted me a photo of a lush garden behind one of the resort’s buildings—a secluded, picturesque spot where he and Steffane would later enjoy dinner as an engaged couple. It was the ideal backdrop.

Poppin’ bottles.

     As always, I arrived early—annoyingly punctual, in fact—to scout the location and gauge how the light would behave during golden hour. This magical time of day, when the sky bathes everything in soft, warm tones, is crucial for capturing that timeless, cinematic feel.

     In a strategic move to elevate the quality of the proposal footage, I decided to enhance the audio coverage using a DJI Mic cleverly hidden under Jean’s shirt. I asked him to arrive ahead of time so I could rig the microphone without raising any suspicion. He then returned to the room to regroup and rejoined Steffane moments before the big surprise.

Top to bottom, all was covered.

     I hid in plain sight on the left-hand side of the ocean-facing steps, camera in hand—my trusty Canon R6 Mark II, paired with the versatile RF 70-200mm lens, which lets me stay out of sight while still capturing every detail. I also had a GoPro Hero 13 Black strapped to my shoulder to provide Jean with behind-the-scenes footage he had requested.

     At just the right moment, I watched Jean drop to one knee, and I began shooting. With the telephoto lens, I was able to capture both wide environmental shots and those intimate close-ups that tell the full story. Thanks to the hidden mic, I recorded the entire exchange in crystal-clear audio—making the final video all the more emotional and powerful.

So classy these two!

     After Steffane said yes, I introduced myself, admired the ring, and congratulated them both. Though I had previously taught tennis at the St. Regis, this was my first time shooting a destination proposal at the resort, and it hit differently. It was my 25th proposal in Puerto Rico in just three months, but each one is unique, and this one felt especially meaningful.

     With golden hour fading, we transitioned to the beach for their engagement portrait session. The beach offered plenty of space to play with, and this is where I shine—capturing candid, romantic moments that feel unscripted and deeply personal. These quiet in-between shots—the whispers, the embraces, the shared laughter—are some of my favorites, especially in timeless black and white.

Golden Hour hits different.

     As the sky transitioned into dusk, I brought out my Godox AD200 Pro Mark II and AD100 Pro flashes to simulate sunset lighting. This allowed me to maintain that warm, glowy atmosphere even as natural light dwindled, and close the session with vibrant, dynamic portraits.

     Jean and Steffane were a dream to work with—classy, fun, and fully immersed in their moment. I feel honored to have played a small part in their love story and to have documented such a significant milestone.