Photos by Rob & Jill Futrell St. Augustine Photographers
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Two people stand on a pebbly shore, one in a gray shirt turning toward the other in a green dress who laughs.
September 29, 2026

Proposal Highlight

Mason & Caitlin’s Proposal

Photographed by Rob & Jill Futrell

Downtown St Augustine Castillo de San Marcos St. Augustine Bayfront Plaza de la Constitución

Mason and Caitlin were in town from Kentucky when Mason got down on one knee along the water with the Castillo de San Marcos as the backdrop — a spot he'd picked out and planned with us ahead of time, right after he asked Caitlin's dad for permission. Jilly and I spread out so we could both catch Caitlin's reaction, and she was completely surprised. After the yes, they showed off the ring and we wandered to a few of our favorite spots around town, including the cobblestone side streets downtown. Then we sent them off to dinner with Caitlin's family.

Rob and Jill Futrell, St. Augustine photographers
Rob & Jill

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