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John and Gianna, Surprise Engagement Proposal | Boston Engagement Photographer

Updated: Sep 9, 2025


Man kneeling and proposing to a surprised woman on a lakeside path. She's in a blue dress, with boats and water in the background.

On a rainy summer day in South Boston's Castle Island, the sweetest couple got engaged. After Sunday Mass, John and Gianna took a walk along the beach where I was waiting and stealthily taking photos of the scenery while I waited for John and Gianna to reach the spot where John would propose. While John and I made subtle eye contact as they approached the area, John dropped to one knee and the rest was history! This location is a special place for J&G (and also became my new favorite!), where they often went as a couple, and it now will be a place they can always have in their hearts where they got engaged!


Keep scrolling to see some of my favorite photos from their engagement session!



John + Gianna | Castle Island, South Boston | 07. 27. 2025

Man kneeling and proposing to smiling woman on a beach path. She's in a blue dress, he's in white shirt and blue dress pants. Water and boats in background.
Man kneeling and proposing to smiling woman on a beach path. She's in a blue dress, he's in white shirt and blue dress pants. Water and boats in background.
Man kneeling, proposing to woman in blue dress by a lakeside beach. Boats in the background, emotional and romantic scene.
Couple kissing on a beach, the woman in a blue dress, the man in a white shirt and blue pants. Boats are in the distant water.
Hands up against a blurred seascape; one hand wears an engagement ring, the other a watch. Black and white, evoking a serene mood.
A smiling couple touches foreheads on a beach, the woman in a blue floral dress holds the man's face who is wearing a white shirt. Sky and ocean in the background.
A smiling couple touches foreheads on a beach, the woman in a blue floral dress holds the man's face who is wearing a white shirt. Sky and ocean in the background.
Couple embracing on a beach. Woman in blue floral dress smiles up at man in white shirt. Calm sea in background, creating a joyful mood.
A smiling couple on a beach. The man in a white shirt hugs the woman from behind. She wears a blue floral dress, and both appear joyful with a sea background.
A couple holds hands, smiling while walking on a pebble beach. The man wears a white shirt; the woman a blue dress. Ocean and boats in view.
A couple embraces on a pebbled beach, gazing lovingly at each other. The scene is black and white, with a calm sea in the background.
A couple smiles while leaning on a green railing by a beach. The woman wears a blue floral dress. Overcast sky and distant boats visible.
A couple leans on a green railing, smiling by a beach. He's in white, she's in blue floral. It’s a cloudy day with trees in the background.
A couple smiling at each other on a beach, arm in arm. The mood is joyful. Background shows the sea and distant boats. Black and white image.
A couple kisses on a sandy beach, with the man leaning the woman back. She wears a blue floral dress, he wears a white shirt and blue dress pants, and the sea is visible in the background.
A hand with a diamond ring gently holds an arm. The person wears a blue floral dress displaying affection.

Boston couples: if you recently got engaged and are looking to capture this momentous occasion, fill out my contact form and let's chat! Click here to get started!

 
 
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Taylor Rossi Photography offers headshots, event photography, family photos, engagements, & intimate weddings in Boston, MA and beyond.

Taylor Rossi Photography is an LGBTQ+ and Woman-Owned business. All are welcome here!

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