Naples City Dock Surprise Proposal {Sebastian & Jessica}

Naples City Dock

Setting Sail For A Magical Surprise Proposal

Thoughtful (and sneaky!) groom to be Sebastian partnered with us to ensure his surprise proposal to Jessica was not just successful, but absolutely magical. From concept to completion, we are so thankful to have been along for the sea-salted ride! Sebastian dreamed up the moment, and we were honored to pull together fellow Southwest Florida vendors to make it happen! Pssst…no surprise here, Jessica said “YES!” 😉

We set sail off of Naples City Dock with a secret plan and a soon to be happily engaged duo. Just peeking at their photos again gets our hearts racing! It was a one of a kind night. To hear the sneaky snippets of how we tricked Jessica together, and see the photos of *the* moment, dive in below.

Naples City Dock surprise proposal

The Scoop on this Surprise Proposal

The magic, as always, lies in the details. When planning and photographing a surprise proposal, this is more important than ever. We poured over each moment during planning with Sebastian. When the very special day came, we put on our very best game faces. Off to sea we went! The ring was in Sebastian’s backpack. Lisa, one of our photographers, had to grab it when they weren’t looking and swiftly put it in her fanny pack. We were pretending to do marketing for the sailboat company. To Jessica, Lisa “was part of the crew.”

The Captain told the couple “they got lucky.” The Captain further fibbed by sharing that “the other family had cancelled, so it would be just the two of them on the boat.” Lisa was pretending to take photos of them, and while out on the deck, told Jessica to turn around for a pose. That’s when she slipped Sebastian the ring. With Jessica’s back still turned “posing”, he got down on one knee. Lisa then said, “Oh, I don’t like this pose.” She asked Jessica to turn around for a new photo. What Jessica saw instead was quite the sight! Her dearest person kneeling before her with a sparkly new accessory. Engagement bliss!

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To Sebastian & Jessica: thank you so much for allowing us to set sea beside you! We wish you both an engagement season and lifetime of swoonworthy seas!

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Written by Social Curator: Kelsey Pfleiderer