Wine Tour - more than 2 vineyards, pick up from Castellina in Chianti


New member
Hi Everyone,

We'll be staying as Castello La Leccia for 4 days next September and we'd love to do a wine tour on one of the days. We're having a problem finding what we'd like though, can anyone advise on if something like this exists, any personal recommendations would be greatly recieved:

  • Pick up from accomodation or start in Castellina in Chianti - we'll have a car but we don't want to taste and drive and a lot of the tours we've seen start in Florence or Sienna again not good because we'd have to get there and back.

  • A tour that has 3 or more vineyards. So many we see are 2 only and then a tour of the countryside. As we're staying in the countryside we can do the sightseeing on our own

Many thanks



New member
Wine tour

Hi Matt,

Chianti is strongly tied to its fine red wine and its wine culture which began with the Etruscan civilization. The Chianti region is one of the most beautiful and famous areas in Tuscany.

Chianti's gentle hills are sketched by miles and miles of vineyards that extend over the provinces of Florence and Siena, covering all the area between both cities.

You will find many farms, wineries and wine cellars that will proudly offer their products and explain their specific elaboration. All wineries in Chianti allow us to experience the real taste of wine. You just need a good Chianti map to start your wine tasting tour, either by car or by bus. The area of Chianti produces different types of Chianti depending on the area. But I want to focus on one of the eight types that you can find: the Chianti Classico.

There are thousands of wineries and farms around the area. Greve is a good example of a wine production town, and you will find shops like “Le Cantine” offering you the opportunity to taste and buy your favorite wines.

Some places around this town are the Castello di Vicchiomaggio, a castle immersed in over 130 hectares of vineyards, and the Castello di Verrazzano, where they organize several types of wine tasting tours to meet several types of requests.

Another fascinating and easy-to-reach place is Panzano, one of the most populated towns in Chianti. This small town is famous for its wine production. Not too far from its center stands the Antica Fattoria Montagliari which offers several wines for tasting, from Chianti Classico Riserva (special vineyard selections), grappa, olive oil and other typical Tuscan products.

Around this area we will find one of the most visited cellars: Antinori’s. Twenty-six generations of The Antinori family have been involved in the production of wine for over six centuries. The family has always directly managed this work. The new cellars have become a space where one can discover the pleasure of “breathing wine” and discovering the phases of its birth and growth: pressing, fermentation, and aging. Tradition, passion, and intuition have been the pre-eminent qualities of character, which have led to the Antinori success in Italy and all over the world. You can book you visit online if you are interested and want to learn more about the production of one of the best wines in the world.

It is important to know that despite sharing a single grape—Sangiovese—and a similar climate and growing conditions, Chiantis are some of the most diverse wines in the world. After a good wine tasting tour you will be able choose your perfect Chianti Classico!


Well-known member
Chianti Tours

Dear Matt,
you're completely right, tasting Chianti wines and then driving is not a good idea: you'll risk a pricey fine if your un into police, and that is not such a far chance!

Taking advantage of tours is the best option if you really want to enjoy both food & wines, and the enchanting Chianti landscape. There are many and some are also private. Most of them actually starts in Florence or Siena and I perfectly understand your objection. I suggest you email the tour company your questions to see if they could pick you up at your accommodation or in Castellina in Chianti on their way; take a look here
in general, but more specifically here
(click on See details and then on the email picture on your right).

Just to do an example, the first stop of this tour
is Castellina in Chianti.

I've seen many offer two wineries, but in some cases you're also offered a complete lunch in typical local restaurants besides the wine tastings at wineries, so it could be a great deal. The tour of the surrounding countryside is quite inevitable, since the Chianti is mainly characterised by endless green rolling hills covered with vineyards and olive groves and actually you can't tour the Chianti area without stopping and taking some pictures of the landscape!!

This tour includes three wineries plus a complete lunch in a typical Tuscan farmhouse:
It starts from Siena and heads to Montalcino, so Castellina in Chianti is a bit out of the way, but I think it could be worthy a drive to Siena just for leaving your car parked and start the tour.



The Tuscan Expert ;-)
Staff member
Ciao Matt,

As Nerea has written, there are hundreds of wineries in the Chianti area and she has offered several that you can do on your own. But I also see the dilemma if you want to do 3 in one day: you really should give the driving over to someone else (as you already decided it is for one's own better enjoyment).

Aside from Chiara's great suggestion of doing the Montalcino tour departing from Siena (as it will take you into another great wine area), I'd also suggest contacting the Castello where you're staying at. I see on their website that they do offer help in organizing private tours directly from them, so it would definitely be even more convenient than even starting from Castellina in Chianti. If you were to just get a private driver rather than a packaged tour, you could actually choose which wineries to visit and just have him/her drive you there. Or ask them to help set up tours/tastings at local wineries and arrange them for you. Most of the owners at the lodgings are happy to help set these things up for their guests and offer suggestions themselves as to which ones might be better.
You can also then decide whether you just want to stay in Chianti or go further away into other wine territories: from the Brunello di Montalcino to Rosso di Montepulciano to Vernaccia di San Gimignano... there are many different wine regions in Tuscany to explore and taste!