Ashley and Stefano

Ashley's Proposal in Tuscany, Italy

How We Met

Stefano and I have known each other for over 10 years. We had the same group of friends. He was either in a relationship, or I was. But whenever we hung out, he was always making me smile. One night, 5 years ago, we had been at a mutual friends house. We just clicked. From that night on we sent each other messages, and it finally led to an official date. From that first date, we knew we had something special. Five years later we’re engaged and living in our own home.

How He Asked

We were heading on a trip to Italy to meet up with his family who had left a few days earlier. His parents were celebrating their 30th wedding anniversary. Our first stop was Tuscany. It was always a dream destination for Stefano and I as we LOVE wine and visiting wineries. I noticed he was a little anxious during the plane & car ride but thought nothing of it. The drive from Rome to Tuscany was about 3 hours. As we were getting closer to Tuscany, Stefano mentioned we should stop to take pictures since the scenery was so beautiful. We were about 10 minutes away from the winery that we were staying at and found a beautiful setting along the side of the road. We pulled over and set up our Polaroid Cube (like a GoPro) so we could snap some pictures. As a complete accident, I set it to record. Stefano took the opportunity and got down on one knee.

He expressed his love and made me fall to my knees. It was so perfect & private – a moment shared with just the two of us. After the proposal we got back in the car and drove for a few minutes to arrive at the winery. His parents, sister & her friend ran straight towards us knowing what had happened. We were able to celebrate our proposal for the next 10 days with family and friends. When I asked why he chose Italy, since his parents were celebrating their 30th anniversary, he said he wanted our love to be just like theirs.

Where to Propose in Tuscany, Italy