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.
