Some engagement rings arrive in velvet boxes. Others spend the afternoon being transported around Edgartown Harbor in a cooler full of drinks.

On a perfect summer day, Jordan Doerr surprised Margaret “Molly” Marks with a proposal that was equal parts thoughtful, cinematic, and completely unexpected. Jordan, who spent summers on Martha’s Vineyard with his family growing up, knew the Island was the only place he wanted to ask the question.

The couple boarded a private boat named Clover for what Molly believed was simply an afternoon on the water. Unbeknownst to her, Jordan had carefully hidden the engagement ring inside the beverage cooler rather than risk carrying it in his pocket.

As the boat cruised through the harbor near the Edgartown Lighthouse, Jordan suggested they take a photo on the bow. The captain helped Molly to the front while Jordan lingered behind, pretending to grab another drink. Moments later he appeared beside her, dropped to one knee, and asked her to marry him.

What Molly didn’t realize was how many people had quietly helped orchestrate the surprise. Family members coordinated behind the scenes, while Island photographer Randi Baird waited nearby on another boat to capture the proposal as it unfolded. Baird also flew a drone overhead, preserving the harbor, the boats, and Molly’s stunned reaction from above.

Afterward, the newly engaged couple memorialized the occasion on the water with family, turning the proposal into an all-day harbor celebration.

Jordan and Molly will marry this fall in the Florida Keys.