A Surprise Marriage Proposal at the Hyatt Regency Grand Reserve in Puerto Rico

The perfect setting: Josiah chose the Hyatt Regency Grand Reserve in Puerto Rico, one of the island’s most beautiful venues, for his surprise proposal to Rosie.

     Every proposal has a story worth telling, and Josiah and Rosie’s is one for the books. When Josiah reached out to me via my website about a month before his big day, I knew immediately that his vision was heartfelt. After selecting a virtual meeting through my contact form—a service I offer to make planning stress-free—we broke the ice online.

     During our chat, Josiah shared that he met Rosie not on Tinder, as I mistakenly thought at first, but on Twitter. Their connection grew steadily, especially during the pandemic, when they leaned on each other through the uncertainties of Covid and quarantine. After five years together, Josiah was ready to take the next step: a destination proposal in Puerto Rico.

Choosing the Hyatt Regency Grand Reserve in Río Grande

A love five years in the making: Josiah and Rosie met on Twitter and grew stronger together during the pandemic before saying “yes” in Puerto Rico.

     Josiah selected the Hyatt Regency Grand Reserve in Río Grande as the venue for the big moment. While the resort is also one of Puerto Rico’s most sought-after wedding venues, I’ve had the honor of capturing numerous proposals there. The tropical setting, lush greenery, and beachside sunset views make it an unforgettable backdrop for engagements.

Preparing for the Big Moment

She said yes: Rosie’s emotional reaction captured the surprise, joy, and love of the moment.

     I never approach a proposal without preparation. For Josiah, we did a quick phone rundown where I emphasized two important things: staying calm and not rushing the moment. Too many times, clients have knelt down almost instantly after walking onto the scene, leaving little room to capture the buildup. I reminded Josiah that soaking in the moment—the handholding, the teary eyes, the anticipation—would make the proposal itself even more powerful.

     Josiah was all in. Confident, steady, and sure about his decision. Since he also wanted video coverage, I arrived early on proposal day to scout locations. With input from my associate Carola and Hyatt’s on-site guide, Jacob, I discovered the perfect grassy area near Building 9. Framed by two large boulders, it felt private and symbolic—ideal for capturing a once-in-a-lifetime memory.

Behind the Lens: Planning the Shot

The moment is too good to not soak it in at the Hyatt Regency Grand Reserve

     I met Josiah briefly to rig him with a microphone, though his choice of a white linen shirt posed a challenge. Pro tip: a tank top under light fabrics makes it easier to conceal audio gear. Once he was ready, I set up my Canon RF 100mm f/2.8 for video and my go-to Canon RF 70-200mm f/2.8 for photography, ensuring I could capture intimate moments without intruding.

     As Josiah and Rosie strolled the sandy beach, I crouched behind a bush (a detail we laughed about later) and documented the buildup. Josiah spent nearly ten minutes speaking from the heart before finally pulling out the ring and dropping to one knee. Rosie’s reaction was pure joy—tears, hugs, and the sweetest yes.

Golden Hour Portraits

Golden Hour portraits: We headed to the west-facing beach to capture the newly engaged couple against Puerto Rico’s breathtaking sunset.

     After the excitement settled, I shifted into portrait mode. The newly engaged couple was still glowing from the proposal, which always makes for authentic, emotional images. Because daylight was fading, we arranged for a trolley to take us to a west-facing beach spot for golden hour portraits.

     The logistics weren’t seamless—the trolley was late, and I accidentally loaded into the wrong cart—but we eventually made it to the right place. There, I positioned Josiah and Rosie strategically to block background distractions, ensuring clean, distraction-free photos.

     With my Godox AD200 Pro II flash, I balanced the colors of the sky against the couple’s embrace, using both wide and tight shots with my Canon RF 15-35mm f/2.8. The tropical sunset did not disappoint.

Finishing at the Iconic Dome

An iconic finish: The proposal session ended at the Hyatt’s signature dome, with dramatic lighting that sealed the night with unforgettable images.

     No proposal session at the Hyatt Regency Grand Reserve is complete without a visit to the dome, a signature photo spot for photographers. While the structure’s many pillars can be tricky for lighting, I came prepared with a second flash—my Godox AD100 Pro paired with a CTO gel. This created warm, cinematic tones against the deep blue evening sky, wrapping up the session with a dramatic flourish.

A Quick Turnaround and Lasting Memories

     Within 24 hours, I delivered the full proposal gallery and video to Josiah and Rosie. Their story, from a chance meeting on Twitter to a destination proposal in Puerto Rico, reminded me why I love capturing these milestones. Every proposal is unique, but the joy, the anticipation, and the love are universal.

     If you’re planning to propose in Puerto Rico, whether at the Hyatt Regency Grand Reserve or another stunning location, I’d love to help you capture it. From planning guidance to professional photography and videography, I ensure every detail is documented beautifully.

How to Capture the Perfect Marriage Proposal in Puerto Rico

Sunset beach proposal in Puerto Rico — the perfect golden hour moment.

As a wedding and proposal photographer in Puerto Rico, I’ve had the honor of documenting more than 30 marriage proposals in the past nine months alone. Each proposal is unique, but the goal remains the same: to capture the moment authentically, beautifully, and without stress. Whether it’s a surprise proposal on the beach or an elaborate setup with decorations, my job is to make sure everything is seamless from start to finish.

Step 1: The First Connection

A romantic kneel on the sand with the Caribbean waves as a backdrop.

When I receive an inquiry through my website, the very first step is to set up a virtual meeting. Most of my clients live outside Puerto Rico — in the U.S., South America, or Europe — so this call is crucial. It’s not just about logistics; it’s about breaking the ice, putting a face to the name, and building trust before we dive into the details.

During this call, I ask questions like “Where did you meet?” or “How long have you been dating?” These may sound simple, but they allow me to create a tailor-made experience. More importantly, they help my clients feel valued, appreciated, and heard. Proposals can be nerve-wracking, and it’s my responsibility to ease that tension from the start.

Step 2: Crafting a Customized Proposal Quote

She said yes! Pure joy captured during a surprise proposal in San Juan.

Once I have all the details, I prepare a customized proposal quote that includes everything they need — and nothing they don’t. I deliver this within 48 hours because I know the anticipation is already high.

My most popular offerings include coverage of the proposal itself followed by an engagement session. I also offer video services, as many couples love to share their big news with family and friends on social media. More often than not, clients select hybrid photo and video coverage for the best of both worlds.

Step 3: Securing the Date

Intimate proposal setup with champagne and a private beach view.

Once the couple selects their preferred package, the next step is to secure the date. I quickly send over a personalized packet of literature, which includes the contract and invoice. A 50% retainer serves both as a deposit and as a retainer — once received, the date is locked exclusively for them. This is important because marriage proposals require precise timing, and my commitment to only one couple per day ensures that they receive my full attention.

Securing the date also allows me to begin any advance preparation, whether that’s scouting locations, checking weather conditions, or coordinating with decorators and planners if needed. Affluent couples who want a luxury experience appreciate the peace of mind that comes with knowing their proposal is already prioritized on my calendar. The earlier we finalize, the more we can refine the logistics without feeling rushed.

Step 4: Planning the Logistics

A quiet oceanfront corner, chosen for privacy and breathtaking views.

As the proposal date approaches, we hop on another virtual call or phone meeting to finalize logistics. The location is key, and in Puerto Rico, beaches are often the top choice. Together, we find a spot that’s intimate, scenic, and not overcrowded during golden hour. This ensures privacy and avoids distractions in the background of the photos.

For surprise proposals, I also work with clients to create a subtle “non-verbal cue.” This might be taking off sunglasses, rubbing a beard, or another small gesture to let me know the exact moment they’re about to drop down on one knee.

Step 5: Capturing the Big Moment

Engagement portraits by the water after the big “yes.”

When the moment arrives, I use a long telephoto lens to keep a respectful distance while still capturing the raw emotion of the proposal. Once the question is asked and answered, I step in to introduce myself and meet the other half of the couple. After giving them a few minutes to soak it in, I begin the engagement session.

Step 6: The Engagement Session

Dramatic sunset flash photography for unforgettable proposal portraits.

Every couple has a different vibe — some are fun and adventurous, while others prefer a quieter, more intimate approach. My job is to adapt to their personalities so the session feels natural rather than forced. I often start with candid portraits of them enjoying the aftermath of the proposal: admiring the ring, FaceTiming loved ones, or savoring a champagne toast.

From there, we ease into more creative portraits. Many couples love the opportunity to take advantage of Puerto Rico’s natural beauty, so I often incorporate the ocean, palm trees, or dramatic rock formations. Getting their feet in the sand or water makes the photos timeless and tied to the island’s essence. I also like to experiment with compositions, giving my couples a mix of classic portraits and editorial-inspired imagery.

Finally, I save the most epic shots for sunset. Flash photography during golden hour allows me to create striking, cinematic portraits with vibrant skies and glowing colors. These images often become their favorites — the exclamation point to their story.

Step 7: Editing & Delivery

Luxury proposal photography in Puerto Rico — capturing the beginning of forever.

The very next day, I back up all images and begin the editing process while the magic is still fresh. Backing up immediately ensures their memories are safe — because when it comes to once-in-a-lifetime moments, you can never be too careful. I like to start editing right away because the energy and emotion of the day inspire how I approach each image.

Depending on the package, couples may receive a 24–48 hour turnaround, perfect for announcing their engagement quickly. Having their gallery ready so soon allows them to share the excitement with family and friends almost immediately. Affluent couples especially value this speed, as they often want their announcement to be just as polished as the moment itself.

I carefully curate each gallery so that it tells the complete story — from the anticipation, to the proposal itself, to the celebration afterward. My editing style balances authenticity with artistry, creating timeless images that will look as beautiful 20 years from now as they do today. Delivering the gallery is not the end of the process; it’s the beginning of how my couples relive their proposal over and over again.

Step 8: Beyond the Proposal

Emotional reaction during a luxury marriage proposal in Puerto Rico.

As a token of gratitude, I extend a special offer to couples who hire me again for their wedding: I waive all travel fees. By the time the wedding comes around, they already have a photographer who knows their story, understands their preferences, and has built a natural rapport with them. This makes a huge difference on wedding day.

Final Thoughts

Engagement portraits by the water after the big “yes.”

For me, shooting proposals in Puerto Rico is both an art and a science. I’ve refined my approach to make it stress-free, personalized, and unforgettable for every couple. Whether it’s a surprise beach proposal or a styled celebration with décor, my mission is to preserve this milestone in a way that feels authentic and timeless.

If you’re planning to propose in Puerto Rico and want to make sure every detail is captured flawlessly, I’d be honored to help you tell your story.

Jacob & Gwen’s Unforgettable Puerto Rico Marriage Proposal at Punta Borinquen

Gwen and Jacob at Punta Borinquen Beach in Aguadilla, Puerto Rico

     A young man named Jacob reached out to me via my website about a month ago, letting me know he wanted to propose to his sweetheart, Gwen—the girlfriend he met a very long time ago.

     Immediately, as per usual, I went ahead and invited him to a FaceTime call not just to break the ice, but to get a feel for where his head was at, catch his vibe, and get to know his story. It’s customary for me as a wedding photographer in Puerto Rico to get the prospective client face-to-face (mostly through virtual meetings because most of my clients are destination clients) and learn the vision they have for their special day.

It was all a blur.

     Jacob proceeded to tell me he wanted to propose with a west coast sunset, namely at a beach usually reserved for surfing and aptly called Surfer’s Beach. It’s one that I’m actually familiar with from my days visiting my father as a child, since he lives in the city where the beach is located—Aguadilla.

     The funny thing about all of this is that I was there a week prior to Jacob’s proposal day scouting locations for yet another proposal. It turns out that another client wanted to propose in Rincón, a city not too far away from Aguadilla. But the path of Hurricane Erin just north of Puerto Rico the day before rendered Rincón incredibly ugly. The sargassum was everywhere, the waves were monumental, and the water was muddy.

Jacob at Punta Borinquen beach in Aguadilla, Puerto Rico

     That’s when I went to Aguadilla because I had remembered an isolated, private, and spacious beach called Punta Borinquen that I also frequented as a kid. Not only did I end up visiting, but I took a video for both my client that day (of which he approved) as well as Jacob’s proposal a week later. I sent it to Jacob, and shortly thereafter he agreed that it was much more of an ideal setting for his marriage proposal in Puerto Rico.

     As a fun side note, Jacob texted me a few days prior with what he called a “non-proposal” related text. He simply wanted to know how he could get back to the city after taking an Uber all the way to the west coast—something that can be quite pricey. Out of the goodness of my heart, I told him he could simply ride back with me since I wasn’t planning on staying overnight in Aguadilla. He couldn’t believe my gesture and was incredibly grateful to have a courteous human being for a proposal photographer in Puerto Rico.

Gwen in awe at Punta Borinquen Beach in Aguadilla, Puerto Rico

     I got there extremely early and parked right in front of the Aguadilla airport to text Jacob some instructions. Because I now know there is little to no cellphone service at Punta Borinquen Beach, I needed to make sure we’d be on the same page prior to losing signal. Once I got the “thumbs up” reaction on my iPhone, I proceeded to cut through the golf course that you inevitably have to take to reach this beach in particular.

     As I parked my car and made my way to the sand, I realized that the farthest section was completely wide open, right in front of the tall cliff with the green foliage. I found a stick in the sand, drew an arrow to where I wanted him to propose, and then placed a coconut next to it so that he could easily find his spot for the proposal in Puerto Rico.

Never let a good silhouette pass me by.

     As the clock neared 6:00 p.m., I made small talk with a photographer from Utah who happened to be there and noticed I had my camera equipment. As part of the pleasantries we exchanged, I kindly asked her to peek over my shoulder to see if Jacob had mustered the courage to propose to Gwen at the location I had designated. When she gave me the green light, we were off to the races.

     I used my trusty Canon RF 70-200mm f/2.8 IS L USM lens to capture that magical moment—a lens I once considered selling but will never let go of because of the vast number of proposals in Puerto Rico I’ve been privileged to photograph. After the dust settled, I quickly introduced myself in person for the first time (something that’s the norm for me as a destination wedding photographer in Puerto Rico) and exchanged some quick banter with the newly engaged couple.

Ring shots are so dreamy!

     Shortly thereafter, I switched to my Canon RF 50mm f/1.2—my favorite lens of all time and one I use often to capture those raw, intimate moments with my couples during engagement sessions in Puerto Rico. It renders so beautifully and allows me to convey the affection and love couples share right after they say “yes” to one another.

     To put the finishing touches on yet another epic Puerto Rico marriage proposal, I pulled out my favorite flash, the Godox AD200 Pro Mark II, and worked with the extremely gorgeous sunset we were blessed with during Golden Hour.

Puppy love.

     I’m honestly floored by how ethereal this session turned out, and I highly encourage you to contact me if you’d like to have your marriage proposal in Puerto Rico photographed. This island offers breathtaking backdrops, heartfelt moments, and unforgettable experiences—something Jacob and Gwen now know firsthand.

Epic finish.

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.