A Sunset Proposal on a Sailboat in St. Augustine | Juan + Kate
- Amanda Provenzano
- 2 days ago
- 2 min read
Looking for the perfect St. Augustine proposal idea? Let me tell you about one of my favorite moments photographing a surprise proposal on the water! It was romantic, emotional, and 100% unforgettable.
Juan and Kate’s sunset sailboat proposal in St. Augustine, FL was straight out of a movie (I’m still not over it!). The whole thing was a secret mission and I got to play the undercover role of a First Mate for the evening. Yes, really!
The Set Up
When I arrived at the docked sailboat at St. Augustine Sailing, Kate’s parents were already on board. They were in on the surprise, of course, and so excited to be part of such a special moment. My job? Pretend to be part of the boat crew! So when Juan and Kate stepped aboard, I greeted them, asked if they’d like a drink, and did my best impression of someone who actually knows how to tie knots and handle sails. (Spoiler: I may or may not have actually been helping with the ropes at one point!)
As the sailboat made its way along the Matanzas River, the sun began to set, casting that dreamy golden glow that makes sunset proposals in St. Augustine so magical.
The Proposal
The plan was for Juan to give me the cue by saying, “Look, a dolphin!” — a simple but sweet line to get Kate to turn around so he could get down on one knee.
And here’s the wild part… just as we were nearing Castillo de San Marcos, the actual Captain spotted a real dolphin swimming nearby. It couldn’t have been more perfect!
Juan said the words. Kate turned around. And just like that, he dropped to one knee and asked her to marry him.
The Celebration
Kate said the most enthusiastic, joyful “YES!” I’ve ever heard. There were happy tears, hugs all around, and lots of celebration. They popped champagne, shared charcuterie snacks, and toasted to forever as the sailboat drifted through golden-hour light back toward the marina.
I still can’t get over how magical the evening was. These two have such a fun, sweet connection, and capturing the moment they got engaged on the water in St. Augustine was such an honor.
Planning a Proposal in St Augustine?
If you’re thinking of proposing in St. Augustine, I’m here to help make it unforgettable. Whether you’re dreaming of a sunset sailboat moment like Juan and Kate’s, a beachside proposal, or something totally unique to your relationship, I’m down to help you plan, keep the secret, and capture it all.
I specialize in surprise proposals, engagement sessions, and elopements here in St. Augustine, FL and I’d love to help tell your story in a way that’s real, romantic, and completely you.
Ready to plan your dream proposal? Contact me here!
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