Tony & Madison’s Yacht Proposal

 

DETAILS
When — September 2022
Where — Monroe Harbor

A voyage of love in Chicago.

Tony is a guy that always goes above and beyond and it really showed with his grand proposal he planned for his girlfriend Madison. He had an elaborate date night planned that toured the city by land and water.

Tony planned to surprise Madison by picking her up in a boat he rented at Knot my Boat Charters. Madison was out with her friends who also knew of Tony’s big plans, so they crafted a story to get her out by the lake shore to rendezvous with Tony. In the meantime, I was in the boat pretending to be part of the crew. My camera was stashed away until the big moment.

Madison was so shocked to see Tony approaching the group by water. She eagerly got on board and then headed to Monroe Harbor to dock and watch the sunset. As they made their way to the bow of the boat I got myself ready and in position to capture the proposal.

Tony took Madison by her hand and professed his love for her and asked her to be his wife. In spite of his sea legs, he managed to get on one knee and propose! Of course she said YES and the two celebrated with champagne with the skyline as a backdrop.

BUT WAIT, THERE’S MORE!

We then made our way down the Chicago River to cruise along the River walk. Tony had one more surprise planned for the night. Tony had all of their family and friends waiting for them at City Winery, where they were able to dock and meet. Madison was so ecstatic when she heard familiar cheers and woo’s as they approached the docks. This was the icing on the cake for this memorable proposal.

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Kevan & Angelina’s Winter Proposal

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Thomas & Makenzi’s proposal at the Shedd Aquarium