Ryan and Olivia had been together two years when he started planning a proposal at The Resort at Longboat Key Club, and he brought me in on the plan from the very beginning. We picked a Friday evening. What we didn’t pick was Hurricane Isaias deciding to pass just west of us that same week, heading north and dumping rain on Sarasota for days.
When the Forecast Doesn’t Cooperate
By Friday, the wind had picked up and the water surge along the coast was intense. Ryan and I talked through what the day might actually look like, and we made peace with the fact that this proposal might not go the way either of us originally pictured. We had backup plans lined up (covered alternate locations in case the beach was a no-go), a plastic poncho ready for my camera gear, and clear umbrellas on standby. Ryan was ready to make the most of it no matter what Mother Nature decided to do, and that attitude set the tone for everything that followed.
A Beach Transformed by the Storm
The rain cleared just in time. The beach was completely empty, storms have a way of doing that, and the water was rushing in higher than I’ve seen it along our coast in a long time. The surge was kicking up so much mist that it created this foggy haze rolling along the shoreline, like something straight out of a romantasy novel (shout out to all my SJM fans, you know exactly the vibe I mean). The light that evening was unreal, and the clouds were doing something I don’t get to photograph very often. Ryan and Olivia both happened to be wearing blue, which could not have matched the moment better.
The Proposal
Olivia let the wind take her hair, and neither of them flinched when the water rushed in without warning, they just laughed and leaned into it. We were all soaked by the end of it, and it was somehow one of the most fun proposal sessions I’ve ever been part of. There’s something about a couple who can take wild weather and turn it into the best part of the story. It felt like an experience none of us will forget, and I feel so lucky I got to be the one to tell it.
Dinner to Celebrate
Ryan had the whole evening planned out, right down to dinner afterward to keep the celebration going. Both of them were an absolute joy to work with from start to finish, and after two years together, they’ve decided on forever. I cannot wait to see everything these two get up to next. Ryan and Olivia know how to make the best of every situation (yes, I’m aware of the lemonade saying, and yes I still used a version of it), they don’t take things too seriously, and they roll with the punches instead of letting a little chaos ruin the moment.
As always, the team at The Resort at Longboat Key Club made everything easy. Staff were incredibly friendly and accommodating, even with a tropical system parked right off the coast.
Tips for a Storm-Season Beach Proposal
If you’re planning a Florida proposal during hurricane season (June through November), a little flexibility goes a long way:
Have a backup location in mind, ideally somewhere covered, in case the beach isn’t an option when the time comes.
Protect your photographer’s gear and your own planning: a rain cover for cameras and a couple of clear umbrellas can save the day without ruining a single photo.
Watch the storm track, not just the forecast. A system passing offshore can still clear up beautifully by golden hour, even when the morning looks like a washout.
Pack a change of clothes. If the water is surging, you will get wet, and that’s half the fun.
Remember that some of the best light happens right after a storm clears. Don’t assume stormy weather means a cancelled session, sometimes it means a more dramatic one.
If you’re planning your own proposal on Longboat Key, I’d love to help you plan around whatever the forecast throws at you. Take a look at this surprise proposal at Zota Beach Resort or Bianca and Patrick’s Longboat Key beach proposal for more Longboat Key inspiration, and if you’re dreaming of getting married on the island too, check out Taylor and AJ’s wedding at The Resort at Longboat Key Club.
