Engagement in Tuscany

img_20160803_133745(8/3) Wednesday started with a trip to Siena, a town towards the south of Tuscany that Leslie really wanted to see. After exploring the city we had lunch at a really cool local restaurant. Away from the touristy area, this was a father/daughter run place and they spoke only italian. Delicious! Afterwards we drove to Castiglione del Bosco, a winery in Montalcino making some delicious Brunello di Montalcino. Its owned by the Ferragamo family and is a nice resort in addition to being a winery. We got a private tour and tasting. The place was really in the middle of nowhere with miles and miles of dirt road to get there. Next, we got a private tour and tasting at a much smaller, lower-key place, Il Palazzone, also in Montalcino. I had told Leslie we had a fancy dinner tonight so she should dress up – and I told her we would drive to a couple of viewpoint spots to take pics. We were in the Val d’ Orcia – a UNESCO world heritage site. I took her to the first one, which was a winding road – got out and took some pics and then onwards to the next spot. It’s called Cappela di Vitaleta, a little church with a couple of cypress trees and a well out in the field. It was a bit of a walk from the parking area.

wedding-proposal-1As we approached, the sun was almost about to set. It was pretty, Leslie was excited and taking pictures as I subtly tried to find the spot the photographers had marked for me. I told Leslie to come over and hold on a moment as I kneeled down. I don’t even fully remember what all I said beyond the explicit question, it all went too fast. But she said yes. That’s when my photographer and wedding planner came out with the bottle of Dom Perignon 2006 and red roses. We had a nice little photoshoot (I am still waiting for pics) and then went on to that fancy dinner.


img_20160803_223916We had dinner at I Salotti, a Michelin 1-star place. I had told them we’d be celebrating the fresh engagement so they set up a nice private room for us with our own sommelier. 6 course, wine-paired meal (food porn below), where he opened a new bottle each time. Amazing. Late night drive back to Panzano (~1.5hrs).






Over the month leading up to the trip I had meticulously planned the proposal. I had researched several photographers, interviewed a few, and selected one that resonated with what I was hoping to accomplish. I needed them to be hiding at the spot of my choosing and be ready to start taking pictures the moment I kneel down. And they did! I am still waiting for the rest of my pics (as of 9/11).  

Picking the right spot also proved to be a challenge. While I found lots of pictures, it was difficult to pinpoint the exact spot. So I hired a wedding planner, someone the photographers recommended, and asked her for what she thought the perfect spots would be. She sent me her list and her #1 choice was mine – so I knew she thought like me. So, I had her bring champagne and roses and present them right after Leslie said yes. (As I had hoped, she brought the Dom Perignon 2006). She also marked the exact spot where I should kneel down to get the best shots – and gave me the coordinates so I could get there.

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