As the sun rose on our second full day in Italy, it seemed wrong- almost sacrilegious- that we had yet to truly try any Italian wine from the Tuscany region.

We technically had Italian wine on our first night in town. After unloading our luggage at our hotel, we instantly got lost on the five minute walk to the restaurant we had picked out. We started out in the right direction, but an alley that looked like a shortcut actually took us a few blocks south of where we wanted to be. Twenty minutes later we found the restaurant, and when it came time to order wine we picked the first Chianti on the list. Chianti is local wine in Tuscany, so we figured it would be just fine.

There’s no question we enjoyed what we picked, but one glass of wine chosen entirely at random after 14 hours of flying, a 30 minute cab ride, and 20 minutes of being surprisingly lost is likely not representative of the region’s best.

Having loved the wine tours we have taken all over the world, we booked a daylong Tuscany wine tour through Viator.com with Walkabout Florence.

Twenty minutes before our tour was scheduled to depart we arrived at our meeting point to find Alessandro, our guide, holding a sign for our tour (called a Wine and Food Safari- “Do you think we’ll see wine and cheese interacting in their natural habitat?” I quipped to Adam as we got into our tour van). By 9 AM, our group of 10 were leaving Florence behind and heading off to our first tasting in the vineyards of Tuscany.

First, a note about Tuscany. If you have been, you know how incredibly beautiful it is. We thought we fully appreciated the landscapes and the architecture after wandering around Florence and visiting both Pisa and Cinque Terre the day before. We were wrong about that. The beauty of Tuscany is multi-dimensional. It’s the rolling green hills and beautiful trees. It’s the vineyards and olive groves that stretch as far as you can see. It’s the flowers that climb up the sides of stone houses and bloom under bright blue, sun soaked skies. It’s the winding dirt roads and the history and the tradition that forever makes this place unique from anywhere else you might visit. It makes you want to learn about it, embrace it, make it part of you.

For us on that day, we set out to discover Tuscany through wine.

Principe Corsini

Our first stop of the day was Principe Corsini, where our morning kicked off with a tour of the estate and a lesson in winemaking. While we have seen how wine is produced as part of many tours, this lesson stuck out because of the history associated with the Corsini family; they have been in the wine business since 1602. We had an opportunity to see both the tried and true processes as well as the more modern technology that makes life just a little easier for the winemakers. The historic wine cellar was a highlight for us; for more than 400 years wine has come from that space, which is just incredible to us- times change, people change, the world itself changes, yet for four centuries Tuscany has been able to count on wine coming from that cellar. Not a bad legacy!

Our tour concluded with a visit to a beautiful loft over the reception area where our group sampled three wines as well as some fresh bread, cheese, and estate-made olive oil. The olive oil was the best we had in all of Italy; it was rich and flavorful and just perfect drizzled on the bread we enjoyed. Our first wine was a sparkling rosé, which was fruit-forward and crisp. I noticed a lot of raspberry and grapefruit; others thought there was a note of oranges. Not usually a rosé fan, I thought it would have been perfect to sip outside in the sunshine. Our second wine was a Chianti Classico, which was a bit floral and spicy all at once. It was instantly a different experience than the wine we blindly ordered on our first night in Florence; it was richer and smoother. Our third wine was a Chianti Classico Reserve, which I thought was the best of the three. It was full of cherries and plums, and the flavor was complex but delicious.
More Information: PrincipeCorsini.com

La Cantinetta di Rignana

After an incredible visit, we were off to our second stop for lunch- and more wine. The restaurant selected for us was La Cantinetta di Rignana, which is owned and operated by a few generations of a Tuscan family. As we approached, though the building was beautiful and the sweeping views of the vineyard and the lush green hills were magnificent, I didn’t have high expectations for the meal. In retrospect, that was silly; some of the best meals we have had have been on similar wine tours, but I often become dismissive of restaurants that I don’t choose (I always figure they will be cheap, touristy, or worse- both of those).

La Cantinetta di Regnana was none of those; we were welcomed with huge plates of delicious, fresh bruschetta. Each of us got to sample the five kinds of bruschetta they brought to us. The classic was incredible, with delicious olive oil and chunks of the freshest tomatoes I have ever tasted. The chicken liver pâté was a big surprise; I’m not usually a fan of liver, but it was satisfying in its creaminess and saltiness. The best of all of them was the truffle bruschetta, which was one of the best bites I had in all of Italy. Our second course was pasta with tomatoes, a delightful dish because of its simplicity and freshness. Our third course was a sampling of grilled meats, most notably some of the best sausage I have ever tried. Each of our three courses was served with a wine pairing (this was a wine tour after all!), and we loved how each wine was so perfectly paired with the flavors in our meal.
More Information: LaCantinettadiRignana.com

Greve in Chianti

After a full hour of nonstop eating and drinking, I was grateful for the free time we had to stroll through the vines in the bright sunshine to walk off some of the food, take some photos, and enjoy the spectacular beauty of the restaurant’s grounds. I was also grateful that we wouldn’t need to eat again for the rest of the day. We boarded the bus, and just 20 minutes later we were in the center of quaint Greve in Chianti.

Greve in Chianti is a beautiful little town that dates back to the 13th century. Today it is home to a number of churches, museums, shops, and restaurants. Greve in Chianti also hosts an annual event called the Chianti Classico wine festival. It happens every year on the second weekend of September.

We had about an hour to relax before our final winery stop, so we did the only thing that made sense after a huge, entirely too filling meal: we had dessert. Alessandro highly recommended we try affogato, which is gelato with a shot of espresso poured over it, and I didn’t want to pass that up! Not surprisingly, affogato became a new favorite dessert of mine after the first delicious bite.

Fattoria di Cinciano

The final stop of the day was Fattoria di Cinciano- specifically the incredible wine cellar where we had our final tasting of the day. We tried two more Chiantis (both incredible- the Reserve that we tried was jammy and intense, and we liked it so much we bought a bottle to bring home).

We also had our first Super Tuscan of the day. Super Tuscans are basically table wines; they are made from several types of grapes, and while they do not need to adhere to the strict rules that govern the production of Chianti, they are made from Tuscan grapes (and often include Sangiovese, but not always).

Our wines were served with fresh bread and salumi that Alessandro purchased in Greve from one of Italy’s most famous butchers. As we sipped and snacked, Alessandro reminded us that we had all vowed never to eat again after lunch. “There isn’t one person here who is still hungry,” I told him, “but that’s a detail we’re willing to overlook.”

As good as the wine was, my favorite part of our stop was how many of the hallways were lined with old wine bottles- some older than me! It was fun to look through them as a few of us found wines bottled in the same year we were born.
More Information: Cinciano.it

Wine Tour of Tuscany

As our final tasting concluded, so did our Tuscany wine tour; we departed for Florence and were back in the busy city an hour later.

I’ve noted before that food (and wine) can serve to be a powerful introduction to people and culture, and this day was yet another reminder of that truth. Especially through the wine we tried we were introduced to a side of Tuscany that dates many centuries back. We got to know about the people who live and protect traditions that have been at the center of Tuscany’s identity for generations. It greatly impacted how we experienced Italy; while it’s great to spend time crossing tourist spots off your list, venturing away from the museums and landmarks so many people visit can give you the space and clarity to really get to know a place.

Our time in Italy didn’t end that day, which was a good thing: the next day, when we ordered a glass of wine with dinner, we did so with confidence. And I’ll never again sip Chianti without instantly transporting back to the beautiful landscapes of Tuscany under the bright blue, sun soaked sky.

Florence Hotels

Are you ready to book a room for your own vacation to Tuscany? Florence is a great place to start your trip. Here are some hotel deals to consider:

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* From time to time, our travels are directly impacted by a service or company. In this case, we booked a tour with Walkabout Florence, and this post includes our candid review of our experience. We selected Walkabout Florence based on our own research and travel needs; we were not offered and did not receive compensation of any kind from them or any other party in exchange for our review. Learn more about our travel philosophy here.