I’ve done wine tastings before. You pull into a winery, hear all about their wonderful product while sampling a flight of four to five wines poured out in small, two-sip portions 10 seconds apart, decide whether to buy, and then head out the door. So, when we set out on a complimentary wine tasting tour in the Chianti Classico region of Tuscany with our hosts Deb of Italy Unfiltered and Massi the Driver, that’s about what I expected. I could not have been more wrong.

Massi, Deb, Steve and Ann

Massi, Deb, Steve and Ann stop for a picture in Tuscany.

The wine tasting tour Deb and Massi took us on in Tuscany was completely different than anything we’ve ever experienced and we loved it! We think everyone who can should taste wine there. And when you go, remember these five tips to help you have the very best experience possible.

1. Have a driver and guide

Having a driver and guide made all the difference in the world. Driving in a foreign country means learning new traffic patterns as well as new road signs. And in Italy it means learning a whole new culture of driving where lane lines and stop signs are often only seen only as suggestions and driving in the wrong parts of town will result in hundreds of dollars in fines. I’m not kidding.

Massi the driver and van

Massi the Driver knew all the best routes and with him driving, we got to enjoy the view.

I didn’t have to worry about any of that, nor did I have to worry about trying to figure out where we were going which it turns out was down lots of winding, hilly one-lane roads with about 2.4 million roundabouts. Instead of arriving white-knuckled and stressed from the drive, I was relaxed and glad to have had the opportunity to enjoy the scenery rather than focusing on the road.

Tuscan hills and vineyards

Looking over olive groves and across the vineyards of Tuscany.

Having a guide was wonderful because we began to hear the stories of the wineries and the wines before we ever arrived at a property. We learned about the natural, organic method used by wine makers in Tuscany, and about how the rose bushes planted at the end of the rows help growers notice potential disease before it reaches the vines.

Roses in Tuscany

Roses like these help wine makers gauge the health of their vines.

We were educated about the grape varietals in the wines, and about the significance of the letters “DOCG” on a label on the neck of a bottle. By the time we got out of the car, we knew something about where we were and what we were tasting. Our experience was so much richer because of it.

2. Take it slowly

Each of the properties we visited were small, family run operations. After arriving, we met our hosts and spent a good amount of time chatting and getting to know them before we ever tasted a single wine. For the owners of the wineries, it felt like it was more about building relationships and showing pride in their work than making a sale. And we liked that.

Wine tasting in Tuscany

Steve and Deb relax on a terrace, enjoying the wine, food, and view.

At one winery, we had a tour of the cellar, seeing the stainless steel vats where the grapes fermented, turning into wine. We then learned about how they use oak barrels to fine-tune the flavor of their wine.

Wine barrels

Wine barrels.

Next, as a bonus, we saw how they press their own olive oil from trees on their farm. As we chatted, we heard the story of how it took 10 years for them to get a permit to build the cellar and their home above, that before then, they had to work out of a shed and constantly move equipment in and out. By the end of the conversation, we actually knew the family and understood the passion they put into their craft.

Steve and Ann with winemaker

Steve and Ann stop for a photo with Sam, one of the wine makers.

When it came time to taste the wine, there were no hurried two sip pours. Instead, the wine maker offered enough of each wine for us to savor, along with heartfelt conversation that made us feel at home on their beautiful properties.

3. Savor the food parings

At each winery, the wine maker offered us food pairings as we sat sipping delicious wines. This wasn’t a plate of cheap crackers or bowl of pretzels, either. Instead, they would pour a wine and then disappear into the house, returning with beautifully plated Italian snacks including prosciutto, bruschetta, cheeses, and olive oil. Every morsel was delicious and served to make the wines even better.

Food pairings for wine tasting in Tuscany

With one tasting, we sere served some bruschetta, as well as prosciutto, salami, cheese, and honey.

At one winery, the owner gave us a sampling of organic jams that she cans from fruit she grows in her garden. We put dabs of these on pecorino cheese from the region and delighted in every single bite.

Tuscan jams

One wine maker offered us homemade jams made from fruits and vegetables in her garden.

4. Stop along the way

Because we had a private driver and guide who knew where we were going and how long it would take to get there, we could stop along the way and explore some locations we never would have found on our own. One fond memory is a stop in a little walled town called Castellina in Chianti.

Tuscan flowers at a winery

Everywhere we looked, we saw beautiful flowers, like these at one of the wineries we visited.

There, we explored the narrow streets, while learning that hundreds of years ago the cities of Florence and Siena constantly fought over control of the town. Today, there is a statue showing how the town has been influenced by both cities.

Castellina in Chianti

This statue, in Castellina in Chianti, shows how the city was pulled toward both Florence and Siena.

Ann has always wanted a big olive wood board to use to serve meats and cheeses at home, and Deb and Massi knew just the place. They led us to a store and said the prices here would be better than anywhere else. I have to admit, we were impressed enough with the price that we bought one, but curious as to whether it really was the best price we kept our eyes open for the rest of the trip. Looking back, I’m happy to report that the board we bought was anywhere from 20-100 Euros ($25-$125) less than any other board we found.

Olive wood serving board

We bought one of these beautiful olive wood serving boards. Deb and Massi knew just where to get the best deal.

And, because we thought it was a beautiful place with a really cool tunnel-like construction along the city wall, here’s another gratuitous picture from Castellina in Chianti.

Tuscany through a window

Peeking out a window in the city wall of Castellina in Chianti.

We had one other unique stop on our tour through the Chianti region, a stop at a Antica Macelleria Cecchini butcher shop that was featured by Anthony Bourdain on No Reservations. We posed for a picture with Don Dario Cecchini, shouting, “carne!” (meat) instead of, “cheese.”

Steve and Ann with butcher

We stopped to pose for a picture with this butcher who was featured on one of Anthony Bourdain’s shows.

As we walked away from the butcher shop, Deb and Massi told us they also offer a meat lover’s tour that stops at this place for a multi-course dinner featuring some of the best the shop has to offer. I can’t wait to come back and sink my teeth into that juicy tour.

5. Revel in the affordable prices

While Ann and I aren’t experts by any means, we are pretty up-to-date with pricing of wines because its something we enjoy.

Chianti wine bottles

Chianti wine in the traditional basket. While a decoration today, originally, the wine bottles were round so they were put in a basket so they would stand up.

Sitting in Chianti, drinking some of the best wines the region has to offer, I couldn’t believe how good the prices were. We were shocked to learn that good bottles of wine were available for 10 Euros, or about $13.00. Even with the cost of shipping factored in, the prices were very reasonable and, I daresay, less than we’d pay in the United States for a similar wine. At times I almost laughed when I saw the price list because I thought they had to be kidding. But that’s fair market price in Italy, and one of the advantages of visiting wineries in Tuscany. Get a few bottles, ship them home, and savor your savings along with the wine.

Oak wine barrel

An oak barrel is used to hold wine as it ages. The oak imparts flavors to the wine.

At the end of the day, I reflected that wine tasting in Tuscany was not at all what I expected. The beautiful scenery, the excellent wines, new information, and friendly company made it far better.

Massi and Deb

Massi and Deb. We sure miss these two.

I am so glad we had access to the expert knowledge of Italy Unfiltered to share with us some of the best wineries the Chianti Classico region has to offer, as well as Massi the Driver to take us right to their doors. We will long treasure the memories we made that day, especially in October when the weather is cool enough for safe shipping and the wine we purchased there arrives.


Our wine tour and transportation were provided to us free of charge by Italy Unfiltered and Massi the Driver. The opinions expressed are our own.


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5 tips for wine tasting in Tuscany.

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