Maybe you’re in the same boat as us and think, “Tuscany in September”, shouldn’t that be the name of Andrea Bocelli’s next hit song? Or maybe even the title of a poem? Who knows, maybe it already is… as for us, we fell in love with Tuscany in September 2015.

Tuscany Italy

The Tuscany region is fairly large and centrally located within Italy. For first time visitors, it can be challenging to pick what areas to visit and which wine regions to experience. We made our way through a large section of Tuscany but focused our wine radar on Chianto Classico. During our time in Tuscany, we stayed in the small town of Greve in Chianti, a province of Florence.

So what makes visiting Tuscany in September so incredible?! Keep on reading 😉

Beginning of Harvest Season:

When most people think of Tuscany, they naturally associate the area with top quality wine, and we’d have to agree! The harvest season varies year by year, but it typically takes place mid-September through October. Visiting this time of year allows you to see Tuscany in all of its glory. Since we were visiting before the grapes had been harvested, we got to see how beautiful the vineyards looked with full grapes hanging from the vines. On the flip side to that, some of the wineries had started harvesting, so we got to experience the wineries in full swing! Grapes were literally hanging from everywhere!

Castello di Verrazzano Tuscany Italy

As mentioned above, we wanted to stay in an area that was known for their production of Chianti Classico which is named for where it is grown. Classico is one of seven sub-regions within Chianti, and Classico must be at least 80 percent Sangiovese grapes. When shopping for wine, you can tell if it an authentic Chianti Classico by looking for the red label with the black rooster seal.

There are multiple wineries to visit, but our absolute favorite was Castello di Verrazzano. For any New Yorkers reading this post, does the name of the winery sound familiar? Castello di Verrazzano gets its name from the Verrazzano family, who once lived on the property. Giovanni da Verrazzano was born in the castle and later turned out to be a navigator and the discoverer of the bay of New York. Hence where the Verrazzano bridge gets its name. The more you know!

Castello di Verrazzano Tuscany Italy

Catello di Verrazzano offers a variety of wine tours, all of which need to booked in advance. We opted to do the Classic Wine Tour for 18,00 €. The tour included a walk through the winery, a sampling of three of their best wines, and some light snacks. If you have time, we’d also suggest making reservations for dinner. All food is handmade, not that you would expect anything less, and the views from the dining area make for the perfect setting.

Castello di Verrazzano Tuscany Italy

Other Wineries in Greve in Chianti:
If you want to visit a vineyard or winery, most require advanced bookings. If you’re just interested in sampling wines, there are many places in the center of town that offer tastings.

Avoiding the Crowds in Popular Cities:

1. Florence:

Visiting the city of Florence can honestly be a blog post on its own as it is one of the most famous and most visited cities in all of Italy. However, it can get extremely busy during the summer months and a bit overwhelming. We’ve visited Florence in both July and September and would much rather visit during the later. While walking around Florence, we noticed it wasn’t as crazy and the lines weren’t as long for top attractions.

Florence Tuscany Italy

2. San Gimignano:

San Gimignano, known as the Town of the Towers, is small medieval walled city located in Tuscany. Of the 72 towers built in the fourteenth century, 13 towers still stand today and offer incredible views of Tuscany’s famous rolling hills. Most people who visit this small Tuscan town come for the towers, just as we did. We climbed to the top of one of the towers and could see for miles and miles. The town is also very well persevered and dazzles visitors with its Romanesque and Gothic architecture.

San Gimignano Tuscany Italy

View from the top of the tower

San Gimignano Tuscany Italy

If you’re looking to grab a glass of vino or do quick wine tasting, visit Museo del vino Vernaccia di San Gimignano. Located in an ancient mansion, this museum offers visitors a chance to take in the views of San Gimignano while sipping on some local wines. The museum also includes images and artifacts relating to the history of this small town. We spent about an hour just sitting outside, drinking wine and taking in the scenic views.

San Gimignano Tuscany Italy

San Gimignano Tuscany Italy

3. Montefioralle:

The small fortified village of Montefioralle isn’t considered a popular city as it is off the tourist track and is virtually car free. However, it worth a visit if you’re staying in Greve in Chianti. It only takes about 15 minutes to walk around the whole village, and there are small passageways to explore as well as views of vineyards in every direction.

Montefioralle Tuscany Italy


When starting to plan our Tuscany trip we had no clue there were so many markets! Markets in Italy sell a range of products including produce, clothing, home goods, etc. If you want to go market crazy, there is literally a market to go to every day of the week. Most markets run all year from 7:30 – 1:00 pm. Below is a breakdown of when and where to go:

  • Monday: San Casciano
  • Tuesday: Poggibonsi, Firenze and Strada in Chianti
  • Wednesday: Siena and Certaldo
  • Thursday: San Polo and Antella
  • Friday: Grassina
  • Saturday: Barberino Val D’Esla and Greve in Chianti
  • Sunday: Panzano

Greve in Chianti Tuscany Italy


Driving Around:

Driving around Tuscany should be a bucket list bullet point for anyone. While visiting Tuscany, we would just hop in our Fiat500 and drive where ever the windy roads took us! One trip not to be missed is along the Strada Regionale 222 Chiantigiana. It runs from Florence to Sienna through the middle of the Chianti Classico wine region. In September, this road was filled with wineries about to get ready for harvest season. We were always stopping to snap a photo and felt we could have been easily dreaming because the area was so beautiful.

Tuscany Italy

  • Lunch Stop: Antica Macelleria Falorni aka Old Butcher Falorni located in Greve in Chianti has been in business since 1806 and boasted some of the best meats in the area. Go for their meat and cheese platters and don’t forget to stop in the store to do some extra shopping! 😉

Antica Macelleria Falorni Tuscany Italy

  • Dinner Spot: Da Padellina, located in Strada in Chianti was hands down the best meal we had in Tuscany. The Fiorentina steak, a strictly selected cut from the regional cows, is their specialty and was the best steak we’ve ever had.

To be honest, we’re sure you could visit Tuscany anytime of the year and it would be wonderful. But for the sake of this blog post and from our experience, we are big fans of visiting Tuscany in September.



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