Our Tuscany fairytale wedding story began when Jarrett and I met at Osler Bluff Ski Club in Ontario. He coached ski racing and I was behind a desk, helping run the racing department. Jarrett made the first move by asking me out for a Canada Day boat trip “with a group of friends”, meanwhile knowing it was going to be couples only and he was setting up our first date! We soon realized we had a deep connection and spent time together over the next few months getting to know each other. Our relationship grew stronger despite the challenges of a global pandemic, leading to not only one house move but two!

The proposal a few years later took me completely by surprise. Jarrett brought me to our new home, which was almost move-in-ready after a 10-month reno project, under the guise of another idea for the space. Before I knew it, he was down on one knee! He made the proposal intimate and sweet, which was perfect.

When it came time to plan our wedding, we were a little unsure of what direction to go in. Jarrett was hoping for a smaller, more intimate ceremony, and as a wedding coordinator who has witnessed so many wonderful events, I was hoping for something that felt unique to us and our day. After speaking with our close friends and families, we started exploring the possibility of locations overseas that could host our group and be feasible for planning from Canada.

We found Villa Castelletto, located in Tuscany, Italy, online and, after some conversations with their team, felt it was the perfect fit for us. The planning process from overseas was a fun challenge for us, but fortunately, we found vendors who made us feel at ease while planning from so far away. To split the tasks, Jarrett took on finding the music for the day, as well as narrowing down our list of places to visit while overseas. I used my knowledge of wedding planning to help organize the details of the schedule, table arrangements, and the overall look of the wedding day.

Before departing for Italy, we planned our legal ceremony and celebration at my parent’s chalet in Blue Mountain. We wanted to be able to celebrate with some of the relatives and close family friends who wouldn’t be coming overseas with us, so a garden party-style luncheon was the perfect solution.

Once in Italy, we were able to relax and enjoy the lead-up to the big day. Everything was planned and organized, all we had to do was show up! We started in Rome and travelled up to Florence before landing at our Italian Villa with our friends and family.

The day itself was magical, with unforgettable moments at every turn. From Jarrett’s emotional reaction during our first look to dinner under starry twinkle lights to dancing the night away in a Tuscan wine cellar. As we had gotten legally married in Canada already, we could just be excited and embrace every amazing element of the day. Our sunset photoshoot with our photographer Madeline was truly one of the most incredible experiences of that day, as the sun was setting over the vines and cypress trees, giving off the most golden light. I think I skipped back to our dinner reception after that!

Looking back, we both agree that our wedding day was truly a fairy tale. From the stunning Italian countryside backdrop to the heartfelt moments shared with our family and friends, it was an experience filled with love and joy.

Jane & Jarrett