It’s not easy trying to plan a surprise proposal, and you’d never know it by looking at him, but Mikey had been carrying the weight of this moment for a long time.
He and Kyra met in college and have been dating for the past six years. Both work in tech, both living life on the go, and both (thankfully) having the ability to work remotely or in the office. Mikey had the ring. He just needed the right moment… and a way to pull it off without raising suspicions.
Originally, he had another photographer & winery lined up. But when that plan fell through, he found me through a mutual friend and reached out to Duckhorn Winery in St. Helena and, together with the hospitality manager, Cristian, came up with a backup plan that honestly? Might’ve been even better than the original. That’s where I came in. Or rather, Elaine came in.
To avoid tipping Kyra off, Mikey coordinated with Duckhorn’s incredible staff (shout out to Cristian!) to have me there as a “staff photographer” capturing images for their internal marketing. I had a name tag to really sell it. I walked around to other tasting tables to keep up the illusion. I even posed them for a casual “guest photo” so if they saw me walking around with a big camera, it was not big deal. Hey… if I’m going undercover, I’m going all in!
After their tasting, Kyra and Mikey were offered a private vineyard tour…one of the many thoughtful touches Duckhorn is known for. The tour ended at a table nestled in front of the vines, decorated with gorgeous peonies and a chilled glass of wine waiting.
That’s where Mikey took Kyra’s hands… dropped to one knee… and surprised her with the most romantic proposal.
Her reaction? Shock. Pure Joy. Disbelief. Repeating “Wait—are we really engaged right now? Is this happening??” with the kind of wonder that makes you tear up behind the camera. (Okay yes, I did.)
They shared a quiet toast together, sparkling wine, no red teeth allowed here, and then we wandered the grounds for a mini engagement session. Lavender bushes, vineyard backdrops, golden light… it couldn’t have been more perfect.
Are you thinking of a surprise proposal in the Napa Valley? Duckhorn Winery is an incredible option.
They offer:
Private tour moments that feel intimate and organic
Beautiful vineyard views and garden spaces
A team that’s truly helpful in keeping your surprise a surprise
And of course… wine. Which never hurts.
Planning a surprise proposal of your own? I’d love to help you make it thoughtful, well-planned, and actually fun. And who knows…if things go well, maybe I’ll see you again on your wedding day!
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