Wine Touring in Chianti, Italy

If I had to choose just one thing I was looking forward to on my recent trip back to Italy, it was definitely a wine tour in Tuscany. The last time I visited Italy was when I was 21 (over 10 years ago) and I didn’t even like or drink wine at the time. I did do a wine tour in Tuscany, but naturally, I didn’t appreciate it the same way as I would/did on this trip.

I decided on the Chianti region as at home I love wines from this area, and it’s something that our family has always had on the table at dinnertime. This region is famous for red wines, even though you will find the occasional white and rose, and they make some damn good wines!

Since we weren’t going to have a rental car during this trip to Italy, and even if we did we wouldn’t want someone to have to be the designated driver, we opted to do an organized group tour through CoolTours By Anna.

How to find a good group tour

Here is the thing, if you are like me, then you probably feel that group tours can lose the authenticity of a region or place. When you have moved along from place to place with 30 others on a giant tour bus, you don’t really feel like you’re truly experiencing a place. So what I really wanted to find was a small group tour that visited smaller, lesser-known wineries. Aka I didn’t want to visit wineries that export their wines to Canada already that I could easily walk down the street in Toronto and grab a bottle of their wine, I wanted to have a more authentic experience.

CoolTours By Anna seemed to check off all the boxes for me. Not only was she an excellent guide, and driver, but she also is a sommelier herself so she was able to provide additional context and information outside of the winery’s tastings.

Where can you do wine tours in Tuscany?

There are several different areas to wine tour around in Tuscany. Anna specially offers the following but she also does custom/private tours as well:

  • Chianti
  • Brunello
  • Montepulciano
  • San Gimignano

As I mentioned, I went the Chianti route but there is really no wrong choice when in Tuscany. My only recommendation is if you aren’t big on red wine, to look into the other tours offered for a region that offers more variety.

Wine touring in Chianti

First Stop

We stopped at three wineries during our time with Anna. The first winery was Castello Monterinaldi. This winery was absolutely gorgeous and is set in the Castle of Monterinaldi (hence the name of the winery). It’s in the heart of the oldest historical area in the region and there are documents that date back to 1010 of this ancient location. Only part of the original castle is still standing after World War II, and is surrounded by some ancient houses. Since 1961, this property has been home to the Ciampi family making delicious wines.

We got a tour of the grounds, and the cellar, and then made our way to their beautiful tasting room for our tasting. Our tasting consisted of multiple red wines, plus one bubbly. We also got to taste their wines paired with things like their fresh olive oil, and parmesan cheese. There seriously wasn’t one wine here that we didn’t like.

Second Stop

Our second stop was our lunch stop at Sant’Agnese Farm. This winery and farm is among the hilly vineyards and olive groves. The property dates back to the year 1000 AD, and about 300 years ago the property was bought by a family whose descendants are still a part of this farm today. At this winery, we had a beautiful lunch in their tasting room that came with, of course, wine pairings. I felt like we had non-stop wine here! We tried all different varieties of reds, and all were so delicious!

Our lunch started with a variety of different slices of bread with spreads to try which we liked the best with the wine we were tasting, followed by yummy chicken and cooked spinach. Next, we got a yummy ravioli with red sauce, where they added some of their homemade truffle olive oil (that you can also buy) on top. Lastly, we had a delicious dessert where they drizzled their homemade balsamic vinegar on top of the gelato. This sounds bizarre but honestly, the balsamic vinegar isn’t like anything you’ll find at home in your local store, you could basically drink it straight it was so good.

What was unique about this lunch and place as they pride themselves on being farm-to-table. In order to make that claim, you have to produce a certain percentage of the food you are serving from your land/farm. One thing you will learn is there are a lot of rules in Tuscany for winemakers to really withhold that standard of wines from this region.

Third Stop

Last, but not least, our last stop definitely was the most stunning in terms of views. Querceto Di Castellina has been in the same family since 1945. The estate has next-level views that overlook their massive vineyard. We did a wine tour here of their winery, where we saw the cellar, where they bottle their wines, and some of the process of harvesting. We then went to their beautiful tasting room/patio that overlooked the rolling hills for a tasting.

This venue was beautiful, and they not only do wine tastings here, but you can also do cooking classes, or even stay here if you want an overnight stay.

By the time we headed home we were full of wine, and good food. Our tour felt very exclusive and authentic, and I only wish that I had time to do another part of Tuscany with Anna.

Know before you go

Dress code: There isn’t a dress code in the wineries and you will see people dressed in everything.

Wines: In the Chianti region you’ll find mainly red wines, we only tried 1-2 other types of wines. If you aren’t a red wine drinker, try another area of Tuscany.

How much wine do I get? Tastings are smaller pours, but I found in comparison to tours I’ve done in North America that they had a heavy hand in all three wineries we went to. It’s also probably the only tour I’ve been on where they would top up your glass when you finished your sample.

Do I need reservations? The easiest way to do this is with a tour like Anna’s, however, if you want to do it on your own, make sure to make reservations for your tastings in advance.

Can I buy wine? Absolutely! It was an option at every stop, and they will ship to you too anywhere in the world. I will caveat that they won’t ship to Canada sadly because of our liquor laws.

How long is the tour? I’m sure each tour differs but we were picked up at around 9 am in Florence at our hotel, then returned around 5-5:30 pm.

Other wine content to read:

Disclaimer: This post was written in partnership with Cooltours by Anna. However, as always, everything written within this post is authentic to my experience and opinion.

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