On the hillside of an old Tuscan town lies the charming Montefioralle Winery. Run by the Sieni family, this vineyard offers vintages of the Chianti wine that the region is known for, plus the best olive oil I’ve ever tasted.

For many years, I’ve wanted to visit the Chianti region. The main question was how to get there. I craved a more personal experience, so I knew that a big tour bus was out of the question. I’m quite cheap, so hiring a private driver wasn’t an option for me. My husband and I flirted with the idea of renting a car, but wanted to see the area first before making the commitment of driving. The winding, hilly, narrow Chiantigiana road may be perfect for pictures, but seemed like a hair-raising drive for two people who had never driven in Italy. Thankfully, a public bus provided us easy (and economical) access from Florence to Greve-in-Chianti. We figured from there we could walk to a vineyard.

Once Greve was defined as our central area, I started planning our day trip. There were several major wineries in the area, including the large castle and estate of Castello di Verrazzano. I briefly flirted with the idea of journeying over to Panzano to eat at the restaurant of famed butcher, Dario Cecchini, but decided to just focus on Chianti. Beef would have to wait for another day!

Using Google Maps, I located all the vineyards in a walking distance of Greve. Montefioralle Winery struck my fancy. They offered personal tastings and tours, which really appealed to me. I liked the idea of Jon and I having the experience all to ourselves. Around the same time, HGTV aired an episode of House Hunters International that took place in Montefioralle.

It was a sign.

I emailed them the next day and reserved our tasting.

Florence was unseasonably chilly that day, but with the skies threatening rain, we grabbed our umbrellas, put on a few layers of clothing, and piled on the bus. The journey was spectacularly picturesque with views of rolling hills dotted with cypress trees and rows of olive groves and grape vines. Our bus trip ended near a main piazza in Greve where we found a little trattoria to enjoy lunch.

After dining, we set off on the hill to walk to the winery. The road was quite steep (I think most would prefer driving) and the climb up it was quite arduous. I was happy for the brisk weather because, despite the chill, the hike heated us up quite a bit. When we reached the top of the hill, the 1200+ feet elevation provided a magnificent view of the surrounding countryside. It was spectacular! Photographs couldn’t do justice to the sight upon which our eyes feasted.

After passing through the single street light of town (the road narrowed to one-lane so the light prevented head-on collisions), we arrived at Montefioralle Winery where we were warmly greeted by Manila. She promptly took us on a tour of their cellar.

As it was too cool to have our tasting on the terrace, Manila led us to a charming tasting room with heavy wooden tables and a small window that looked out on the farm. The room had a feeling of antiquity to it that reinforced the heritage of the winemaking craft.

We were served some lovely little morsels of food that showed off their olive oil and accompanied the wine—crostini, polenta bites with ragu, and the like. Manila poured different vintages of Chianti Classico, Chianti Reserva, IGT, and Vin Santo in a vertical tasting so we could understand the aging of the wines and how the characteristics of each vintage differed. She explained the various wine designations, varietals of grapes used, and all the intricacies of the process. We felt welcome to ask lots of questions. Manila’s warmth and kind nature encouraged us to really learn about the wine without fear that she would laugh at our naiveté. After each new pour, she would leave us to enjoy and discuss our Chianti. It’s a testament to their product that I’m not normally a fan of red wines, but happily purchased a bottle of their Chianti Classico—that was consumed mere days later.

The tasting ended with a sweet wine called Vin Santo served with homemade cantuccini (cookies) to dip in it. Unlike vintages I had tried before, Montefioralle Winery’s Vin Santo was complex, smooth, and quite delightful.

Our tasting having thoroughly warmed us up, we tipsily headed back down the hill clutching our treasure of olive oil and wine. It had been an intoxicatingly wonderful trip and we look forward to returning.

I highly recommend visiting Montefioralle Winery the next time you’re in the Chianti region. Here is their website: https://www.montefioralle.wine/

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