Tuscany Day Trip to San Gimignano and Chianti

3 h
Day Trips & Excursions
difficulty Very easy
Wheelchair Not Accessible

Tuscany Day Trip to San Gimignano and Chianti

Join our day trip to San Gimignano and Chianti, internationally renowned wine-producing lands, gorgeous in any season of the year. Discover some of the most charming small towns in Tuscany and eXPerience their traditions: vineyards, castles, green landscapes and typical foods are waiting for you!

A day trip to discover one of the most famous vineyard land in Italy: the town of Chianti
San Gimignano, the famous medieval village, unmistakable thanks to its high towers
Are you a red or white wine enthusiast? Try both of them, in this amazing tour through Tuscany’s wonders
A unique tour to enjoy a good glass of wine and travel through vineyards and medieval villages
If you’d like to spend a different day, surrounded by vineyards and breathtaking landscapes, then this tour for you!

Be enchanted by the charm of the real Tuscany with this day trip to San Gimignano and Chianti: the perfect opportunity to relax and eXPerience the wonderful scenery of green rolling hills and vineyards.
We will leave from San Gimignano town, whose historical centre has been declared as World Heritage Sites by UNESCO: visit the fourteen towers, perfectly preserved, which have earned the city the nickname of the "Manhattan of Tuscany", and discover their legends and secrets.
Then, admire the main church of the city, the Collegiate of Santa Maria Assunta, riot of colors thanks to the Florentine and Sienese workers who have collaborated here. Left to the church is the Palazzo del Popolo with “Torre Grossa”, the only tower in San Gimignano which can be visited and climbed! If you want, you can climb up to the Fortress and take spectacular pictures of the city and its surroundings. But San Gimignano is also the land of pure saffron and Tuscan Vernaccia, high-quality DOCG white wine. An amazing opportunity to combine culture and flavors in one day trip!
The tour will continue to Monteriggioni, a little medieval town strategically placed as a defensive fortification during the conflicts between Siena and Florence in the Middle Ages. Because of its beauty, the city was also mentioned by Dante Alighieri’s “Inferno”: an evocative city, surrounded by high walls which earned Monteriggioni the title of impregnable fortress. Through its narrow streets you will travel back centuries and eXPerience an authentic medieval atmosphere.
We will have a lunch break at an organic farm that produces the renowned Chianti wine. Here, besides tasting genuine local food and high-quality wine, you will also learn more about the Chianti’s manufacturing process and the type of grapes used for its production.
The excursion will end during the evening in the Chianti’s region, where you will have the chance to visit Castellina and Radda, two small villages full of history and culture, immersed in a landscape filled with vineyards and castles.

More Thinghs To Do in Tuscany

If you are staying in San Gimignano, and you want to explore the wonderful landscape of Chianti, you might be interested in the Chianti and Castles Tour or in the Chianti Tour with Brunello Wine tasting.
Also, if you want to discover two charming villages that overlook the Ligurian sea, we recommend the Tour of Portofino and San Fruttuoso from Tuscany!

  • San Gimignano
  • Monteriggioni
  • Lunch break at the "Chianti Classico" organic farm
  • Castellina
  • Radda
  • professional tourist guide
  • guided visit to San Gimignano, Monteriggioni, Castellina and Radda in Chianti's area
  • entrance to the Collegiate of Santa Maria Assunta, in San Gimignano
  • visit to the Chianti's winery
  • lunch and wine-tasting
  • transport
  • tips (optional)
Meeting point: 

Meeting point information and local telephone numbers at your destination are included on your Confirmation Voucher.


We recommend to wear comfortable clothing. 
Also, appropriate clothing is required for the entrance to museums and places of worship.
You are kindly invited to follow your guide and enforce the rules that will be explained, in respect of the celebrations and the places you will visit.
You can book your private transportation service with ItalyXP.

Confirmation will be received within 48 hours of booking, subject to availability. Once your booking is confirmed we will email you a voucher. This is your ticket and proof of purchase.