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Weddings

This Couple Got the Dreamiest Engagement Photos on a Sailboat. Here’s How They Did It.

Hint: It took TWO boats for William Loveless and Madeline Martin's nautical engagement session.

Written by Amy Moeller
| Published on August 8, 2019
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All photographs by Megan Harris Photography

When photographer Megan Harris found out that one of the grooms-to-be she’d be photographing, Will, had been working on restoring a vintage 1960s sailboat, she thought it would be fun to incorporate the project into the couple’s engagement photos. It wasn’t meant to be, though, Harris says, because the boat needed more work before it could be put into the water. So instead, Maddy (the bride-to-be), and Megan set out to find an alternative.

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Fortunately, Maddy works at a college that happens to have a strong sailing program, so, Megan says, she and Maddy got to work on borrowing a boat from the university for the evening photoshoot.

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Ultimately, Megan says, they were able to find a vintage sailboat, about the same year as the one Will was working on, to take out for a few hours. On the evening of the photoshoot, the vintage boat was anchored in the Chester River, so the three of them borrowed a second, smaller, boat to motor out to the vintage boat in—with the help of a driver/boat captain. Once they reached the destination sailboat, Maddy and Will climbed aboard, and Megan stayed in the motorboat, driven around and around the sailboat, to capture this show-stopping engagement session.

 

 

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How They Met: Madeline Martin, the director of events at Washington College, and William Loveless, a network engineer for L2, met in downtown Annapolis at McGarvey’s one Saturday night in late July of 2016. In a matter of minutes the two discussed politics, religion and their ten-year plan. By the end of the night, they say, they each know they’d met someone special. They exchanged numbers, and Will texted Maddy the next day to set up a date. On August 2, the two enjoyed dinner at Lupo Verde, followed by a trip to the Botanical Gardens, and 18 months later, Will popped the question on a trip to Williamsburg.

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This past June, they married at a family-owned waterfront home in Grasonville in the company of 125 loved ones. The couple currently live in Stevensville, Maryland.

 

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About the Engagement Photos: “With their established roots on the Chesapeake Bay, I knew their perfect engagement session would be on the water, says photographer Megan Harris. “Taking their session onto a vintage sailboat on the waters of Chestertown was the perfect way to incorporate their love of the Bay—and romance!”

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Amy Moeller
Amy Moeller
Fashion & Weddings Editor

Amy leads Washingtonian Weddings and writes Style Setters for Washingtonian. Prior to joining Washingtonian in March 2016, she was the editor of Capitol File magazine in DC and before that, editor of What’s Up? Weddings in Annapolis.

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