Dillon and Samantha smiling on a wrought-iron balcony with palm trees and historic buildings

Highlights

Samantha & Dillon

March 8, 2026

Dillon and Samantha took over Downtown St. Augustine for their engagement session, starting in the shade near the Lightner Museum and working their way through the cobblestone streets. Rain was in the forecast, so we moved the session up a few hours, and we were treated to a warm, sunny March afternoon. St. Augustine is always full of surprises, like when we were photobombed by a Model T while they posed in front of a worn stucco wall. We got our steps in by walking up the bayfront, grabbing a few pictures at the marina, and finally wrapped up the session at my favorite—the Castillo de San Marcos.

Samantha and Dillon kiss through a circular stone archway framing the historic St. Augustine skyline and reflection below.

Dillon and Samantha smile together on a wrought-iron balcony with palm trees and historic buildings behind them

Samantha and Dillon walk hand in hand down a tree-lined brick pathway, sunlight filtering through the canopy

Dillon wears a light blue button-up shirt while Samantha wears a sleeveless white dress on a brick-lined downtown street.

Samantha looks back over her shoulder as Dillon holds her close against a chain railing with boats visible behind them.

Samantha in a white dress and Dillon in a khaki shirt on grass with the stone fortress and palm trees behind

Dillon lifts Samantha in his arms as she wraps her arms around him, backlit by bright clouds at the waterfront.

Samantha extends her hand to show Dillon the engagement ring while they stand with the stone tower visible in the background.

Dillon nuzzles Samantha's forehead on a sunlit balcony, him in blue and her in cream

Samantha and Dillon at an arched doorway looking at each other with the cathedral visible beyond the iron gate

A vintage car passes in motion blur while Samantha and Dillon stand against a weathered colonial building

Dillon and Samantha pose together inside a spiral architectural structure in black and white.

Dillon and Samantha stand at a waterfront railing overlooking sailboats in the harbor.

Dillon and Samantha embrace while standing by a metal chain barrier with the bay and sailboats in the background.

Samantha and Dillon face each other on the grass at Castillo de San Marcos with palm trees and stone tower behind

Dillon carries Samantha across the green lawn in front of the fortress tower with palm trees lining the historic site.

Samantha smiles at Dillon as he looks down at her hand displaying the ring, with palm trees and the fortress behind them.

Rob and Jill Futrell, St. Augustine photographers

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Downtown St. Augustine Engagement Photography

Photographed by Rob & Jill Futrell, your St. Augustine photographer team.