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From EUR 150

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Semi-private tour of Tuscany to Siena, San Gimignano, Monteriggioni & the Chianti wine region all in 1 day!

If you are short of time and you are only in Florence for a few days, then this is the perfect tour that allows you to see the best of Tuscany in ONLY 1 DAY! 

Visit 3 of the most famous Medieval villages in Tuscany; Monteriggioni, Siena and San Gimignano with your local tour leader and fall in love with the beauty of this amazing land. End the tour in a scenic winery in the heart of the Tuscany countryside to taste the delicious Chianti wine in the full comfort of a minivan. 



  • Semi private tour/ 8 seat minivan
  • Your English speaking tour leader
  • 2h visit of Siena
  • Orientation walk of Siena with our tour leader
  • Time to explore Siena in complete freedom
  • A short visit of Monteriggioni 
  • 1h30 visit of San Gimignano
  • Free time to discover the villages at your own leisure
  • Scenic drive of the Chianti region
  • Wine tasting in a local winery
  • Up to 8 different types of Tuscan wines
  • Extra Virgin olive oil tasting
  • Truffle oil & pepper oil tasting
  • Balsamic vinegar reserve
  • Authentic Tuscan meal: Antipasti Toscani (bruschetta, pecorino cheese, Tuscan cured meat), some Lasagna with truffle oil, traditional Ribolita bread Soup and Cantuccini biscuits as dessert.

* Available on request, vegetarian, vegan and gluten free menu.


Every Monday, Tuesday, Thursday, Saturday. Other dates on request

8:45 am
We meet at 8:45am in Piazza della Calza by Porta Romana in front of the blue P ( parking ) sign
9h. We return back to Florence at  6:00/06:30 pm approx

> Over 39 are welcome
> Not recommended for people with walking disabilities
> Our team is made of local tour leaders. All information about the villages will be provided during the journey to reach the towns. In each town, you will have free time to walk around at your own leisure. Only licensed tour guides in Italy are allowed to provide info in front of the monuments. If you are interested in a guided city walking tour contact our team in advance to have it organized at extra costs.


From EUR 150

+1 Additional options

Book Now Inquire Booking

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Meet your IOAB tour leader and the other travelers just before 09:00 am and travel in the comfort of an 8 seat minivan towards MONTERIGGIONI, a 13th-century medieval town that was the stage for the famous movie “The Gladiator”. Here you will be able to admire the wonderful views of the area and the Tuscan countryside from the ancient walls or explore the small shops selling the local handicrafts.

During the trip learn from your tour leader interesting facts about Tuscany, its famous products, local food and historic facts about the region and the village. 


Our second stop of the day will be the visit to the historic city of SIENA where you will be enchanted by the architectural styles of the cathedral and the old palace in Piazza del Campo, the venue of the famous Palio horse race held twice a year in July and August. After an orientation walk with your guide, you will be left free to explore the town, sit in one of the many cafes to relax or discover the hidden streets of this magical town.

The tour will continue through the ROLLING HILLS OF THE CHIANTI region for you to admire the many vineyards, olive trees, cypresses and everything that makes this land a dream place including a must-do stop in a LOCAL WINERY surrounded by vines, flowers and olive groves for WINE AND OLIVE OIL TASTING & TRADITIONAL TUSCAN LUNCH. Don’t forget to bring your camera…..the scenery from here is stunning! At the winery, you will TASTE UP TO 4 kind of wines including the famous Chianti Classico wine and Chianti Classico Riserva.


We will then continue towards SAN GIMIGNANO, a UNESCO World Heritage Site and the most famous walled medieval hill town in Tuscany also reknown as the " Manhattan of Tuscany " due to the many towers. On the way to the village our guide will give you tips about the best places to visit and you will have free time to wander through the narrow and characteristic streets and check out the local shops selling Tuscan delicacies. Don't forget that San Gimignano is also the place where the world champion gelato maker is based... so make sure to have some cash with you to spoil yourself.


What else can you ask for? Reserve in advance because seats are limited!


  • The best of Tuscany in 1 day
  • Small groups, no bus tours, no families with crying kids and mainly only 1 language to listen to
  • Mingle with other like minded travelers
  • Discover Siena, the city of the Palio horse race
  • Wander in San Gimignano, the city of the towers
  • Drive the Chianti region, the wine land of Tuscany
  • Taste 4 types of wine & extra virgin olive oil top quality


  1. Firenze
  2. Monteriggioni
  3. Siena
  4. San Gimignano
  5. Firenze