Madeline Island Sailboat Proposal in Bayfield, WI | Minnesota Wedding Photographers | Abbey and Michael

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Greetings, beautiful humans! We are fastly approaching winter over here in Minnesota so we thought we’d take a minute to bring it back to *somewhat* warmer times! So let us tell you about the awesome sailboat proposal we had the honor of shooting this past summer in Madeline Island off of Bayfield, Wisconsin!

Planning the Surprise Sailboat Proposal

Abbey has been my best friend in the entire world for YEARS! We grew up together and have truly been through it all! This girl means the absolute world to me. Abbey lives in South Carolina now with her boyfriend (now fiancè and soon-to-be-hubby), Michael. But we’ve never let some distance stop us before and we don’t plan on doing so anytime soon!

For the past year or so, we’ve been switching off on trips to each other’s states for visits! Aaron and I went to South Carolina in December of 2021 and then they came back here to Minnesota for Christmas. When we were visiting last December, I expressed that I would love to make it an annual thing where we visit each other! I told them that it would be awesome if they came up here in the summer and we took a little trip to Bayfield, Wisconsin and explored the Apostle Islands! They were totally down for it and, just like that, we had our trip planned!

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Now, the trip didn’t start out as a surprise proposal! We knew Michael had been planning to propose and we reached out to ask him if he would want to do something special on this trip while we could capture the moment. After we mentioned that we could to a sunset sailboat ride, he was completely sold and our plan was set in action! I scheduled a dreamy sailboat ride at sunset and we were all set to capture the proposal that dreams are made of!

As the months grew closer and the dog days of summer hit, we were anxiously waiting for this trip! Not only were we super excited to shoot this amazing proposal but it was going to be a little bit of a break from the craziness of wedding season too! We were just so grateful to be able to be there to capture this special moment for these two!

A few days before the big trip, the captain of our sailboat reached out with some bad news. Unfortunately, our captain tested positive for COVID and wouldn’t be able to host our sailboat ride. The panic began to set in as we couldn’t have a sailboat proposal without a sailboat! But we remained calm and, thankfully, we explained the situation to the captain and he was able to pull some strings to get us a sailboat ride with a different captain. We are so eternally grateful for this and we wouldn’t know what we would’ve done without this!

Time for the Surprise of a Lifetime

By the time we rolled up to the airport to pick up Abbey and Michael, we were just so ready for this surprise and little getaway! We stopped at a little coffeeshop for some liquid energy and food before we hit the road to Wisconsin. We had rented a little AirBnB and after a long drive that seemed like it would never end (even though it isn’t too bad of a drive), we got settled into our AirBnB. Before we knew it, it was time for us to leave for our sunset sailboat trip!

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Honestly, it was really hard hiding my excitement! My best friend was getting engaged and I couldn’t seem TOO enthusiastic about a regular ol’ sailboat ride! What brought me back down was that the weather was very cloudy and it was raining off-and-on all day. It sucked that we weren’t blessed with a super awesome sunset but we couldn’t complain because it was just so darn beautiful!

Once on the boat, we were having a blast! Our captain was quite the character and we had some great banter going back and forth across the boat. The nerves were thick in the air as we all awaited the special moment! The rain had stopped but the grey clouds hung around to get in on the action! It was quite cold on the water even though it was the middle of August but we made do!

As Abbey made her way up to the bow of the boat to look out at the beautiful view, Michael flashed a reassuring glance our way. Turning around, Abbey was greeted by Michael down on one knee. The look on her face was absolutely priceless! And as I’m sure you can tell since I’m writing this post, she said “YES!”

This was seriously such a magical moment for us to be able to capture! This was our first proposal we have ever shot and it was so amazing that it was my best friend! We wouldn’t have asked for it to be any other way! I mean come on, we not only got to shoot a proposal but a sailboat proposal!

The Adventures to Follow

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While we were on our sailboat adventure, our captain was telling us about a really cool restaurant back in Bayfield that he recommended! It was an old farmhouse that they turned into a restaurant! He told us that it was kind of hard to get a reservation due to limited seating but was totally worth it if we were able to get it. After we finished with our sunset sail, we reached out to the restaurant, Good Thyme, and they said we were in luck! To celebrate their engagement, we took Abbey and Michael out to Good Thyme! There was amazing food, the service was great, and it was seriously the perfect spot to celebrate their engagement!

The next day, we had our adventure planned to take the ferry over to explore Madeline Island. We had such a great time walking around Madeline Island, exploring all it has to offer. We went hiking and, of course, we brought along the cameras to capture the happy couple as they celebrated their engagement!

A quick, unrelated side note: All of the coffeeshops on the island close at 2! Aaron, Abbey, and I were desperate for an extra boost of energy but all the coffeeshops were already closed! So keep that in mind if you’re coffee snobs like we are and plan on visiting the island!

One of the coolest things we happened to fall upon on our adventure was Tom’s Burned Down Cafe! It’s right next to the ferry landing and you honestly can’t miss it when you get off the ferry! It’s a little bar built on top of these run-down vehicles! It’s such a cool spot to stop and take pictures! Honestly, we just had so much fun reading all of the fun signs that are scattered throughout!

All Good Things Must Come to an End

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For our last day in Bayfield, Aaron and I had scheduled an engagement session over at Cornucopia Beach (We’ll blog about that one soon!) While Aaron and I shot that session, we left Abbey and Michael with the car to go out on their own adventure!

After that, we enjoyed our last night in Bayfield by ordering some pizza and enjoying some quality time in our AirBnB! It was such a great trip and even though we did work for some of it, it made for the perfect vacation getaway!

We are so blessed to have Abbey and Michael in our lives and we are so thankful to help them celebrate this momentous occasion in their love story with this sailboat proposal! They both deserve the world and we are so stinkin’ excited for their wedding next year! It’s going to be amazing!

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As always if you liked what you heard and want to go on an adventure of your own for a proposal or an engagement or just for shits and giggles, bring us along! We’d love to capture that special moment in your life! Contact us here to set something up! If you wanna hear about an awesome memory map engagement session we did, check that out here! Make sure to follow us on all of the social medias linked down below to keep up with our daily adventures!

Keep it cute, friends! We’ll talk soon! xoxo

  1. Mom says:

    This is awesome. Congratulations to Abbey and Michael. KC and Aaron tou do fantastic work. I am impressed!!

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