• Via della Sapienza, 14 Siena
  • +39 3336219136
  • info@wedriveyou.it

San Gimignano, Monteriggioni & Chianti Classico

  • 8 hours

Tour Description

For an activity aimed especially for those who love their wine but don't want to miss the beauty of a medieval hill top village we suggest half a day in the Chianti, tasting wines and enjoying the countryside and views; and for the other half a stop in San Gimignano, nicknamed medieval Manhattan due to its multiple towers. In this amazing hill top village, you should spend some time exploring this amazing hill top village. A recommended day starts from your accommodation with a first stop in San Gimignano, normally best visited first before the tour buses arrive, then proceed into the heart of the Chianti with stops at two boutique wineries, all off the beaten track. Lunch can be organized in a winery and discovering wholesome typical Tuscan food.

Additional Info

Pick up location

Directly from your accommodation


8 hours


In a unique location with typical, local far, excluded from quotes

Suggested Itinerary


Pick up at accommodation


Stop at Monteriggioni, then San Gimignano (optional gelato tasting at a world champion ice cream maker)


Unique, local winery


Tastings in boutique, family run wineries


Drop off at accommodation


Sharon G (Melbourne, Australia):

TOUR: 3 days in Tuscany
We recently used "We Drive you Tuscany" for 3 x full day tours. Everything was organised via email remotely from Australia and it was perfect. Great communication and recommendations initially to us via email.
We were given the same driver for all 3 days so the continuity / relationship was there - so this was great.
We had a very clean and modern luxury Van for all 3 days.
Day 1 Our driver/guide Tomas picked us up from Pisa train station and drove us to Siena - via the beautiful San Gimignano and Monteriggioni pointing out the sights along the way and giving advice about where to go/eat/sightsee.
Day 2 - Tomas collected us from our hotel in Siena and drove us through the Chianti area (Nth Tuscany) stopping at 3 wineries and also for lunch. He even took us to his local coffee shop for an espresso and a little known Etruscan tomb in Castellina.
Day 3 - Tomas collected us from our hotel in Montepulciano and drove us around a number of wineries and sites in the southern Tuscany area.
We recommend this small company and have already passed on the details to others. They were very competitive from a price point of view and nothing was too much trouble. Thanks for a great 3 days!

Lisa I.:

We just returned from a fabulous day spent with Tomas touring the lovely Tuscany region. Our day began in Firenze with a pickup at our hotel followed by a stop at the beautiful palace gardens that overlook the city. Amazing views to be had from this point. From here we left the city to visit several wonderful hilltop mid evil cities including Siena and San Gimignano. We spent time at each village shopping, eating gelato and exploring the incredible ancient buildings that reflect the Midi-evil, Renaissance, and Byzantine periods. We ate a wonderful lunch in Siena and after visiting the sites there headed off to wine taste. Wine tasting was a really fun experience in itself. Quite tasty Chiantis and super Tuscans.
Tomas was an absolute delight and was very informative about Italian history, wine, and everyday topics. He was a joy to talk to. All and all a great way to spend a day seeing many sites and having fun. We hope to be back to perhaps do one of his bike tours!

Ryan Hanson:

Really enjoyed the flavor of Sienna and visiting family-run wineries. Great way to spend day.


TOUR: Wineries with Roberto HD trip
We booked a wine tour for half a day only the night before and received the confirmation following morning! The driver picked us up at our place in Siena with a very nice and comfortable car. Our driver was Roberto, who spoke very well English and is a very funny and nice guy!
He could answer all our questions on Italian cuisine and culture in a very passionate way.
The wineries we visited were as authentic as you could imagine and they let us try all their best wines! We had an amazing afternoon and wished we’d booked for the entire day.
Wedriveyou.it is highly recommended by us and make sure you ask for Roberto!