Summertime sailboat engagement photos at Milwaukee’s South Shore Yacht Club- what better way for two sailors to celebrate!?

Billowing blues storm clouds retreated behind them; the storm had just missed them! As the sun peeled back through the clouds, Emily and Dillon’s session kicked off!

South Shore Yacht Club Milwaukee

How they met

It was a Friday evening Lake Mendota in Madison, WI and the local sailing club was about to set off. It was fate for the two sailors. They continue to be extremely active in the sailing community (and are even planning their wedding at a lighthouse + yacht club on the Milwaukee Bay) Whether it’s real life sailing or racing remote control sailboats, Emily and Dillon live for being on the water! Another reason why photographing their sailboat engagement photos at South Shore Yacht Club was the most perfect fit.

The Proposal

Dillon got a large sign with “Will you marry me” printed, and attached it secretly to our front sail (jib) the evening before with the help of our friends. We were on a sailing trip. As we left Port Washington, Emily unrolled the jib and saw the sign, turned around and Dillon was on one knee with the engagement ring. They both shed a few tears 😉

Engagement Photos Milwaukee

The two expertly maneuvered their sailboat around the shores of Lake Michigan. And the result? Photos that FEEL like Emily and Dillon. In their element. Doing the thing they love most- sailing!

Milwaukee has some of the most unique waterfront views in the state and that includes McKinley Beach. Its long stretches of sandy beachfront and waving seagrass make it the perfect place for a date night! While not a suitable location for swimming (seriously, safety first- those rip tides are no joke!), it is a prime spot for stellar lakefront views (or sailboat engagement photos 😉 )

Milwaukee Engagement Photographers

Our associate Madeline absolutely KNOCKED this session out of the park! She truly captured Emily’s driven, caring personality and Dillon’s selfless, easygoing character. Madeline is a part of the O & B Photo Co Milwaukee engagement photographers team! And the way she captured these sailboat engagement photos shows just how passionate she is (and just how proud we are to have her as an associate!)

The couple describes themselves as having an”old married vibe” -everyone thought we were already married! We like give each other a hard time sometimes, but also have a great time together.” When they aren’t sailing they’re busy fixing boats, doing remote control sailing, watching sailing, and playing with with the loves of lives – their cats Louie and Mads!

Emily & Dillon – thank you for trusting us with the most romantic sailboat ride there there was! Raising our flying jibs to you;)