3-Days Self-drive Wine Tour of the Chianti area, in Tuscany

3 d
Escorted Tours
difficulty Very easy
Wheelchair Not Accessible

3-Days Self-drive Wine Tour of the Chianti area, in Tuscany

Join our amazing tour in the fabulous Chianti wine area, visiting the most impressive medieval towns and indulging in the delicious Chianti wine. This special experience in Tuscany will let you discover the most authentic destinations in Chianti and learn more about the Chianti wine heritage.

Experience the enchanting destinations of Chianti wine area
Visit an authentic medieval castle in Greve in Chianti and sample the wine selection
Discover the heritage of Monteriggioni and Siena, gems of Tuscany
Explore the impressive town of San Gimignano and admire its attractions
Visit the fascinating winery "Enoteca" in the town of Castellina in Chianti

Day 1: Greve in Chianti

Italy is world renowned for its culture, nature, fashion and many more, include exquisite gastronomy. But a truly complete Italy experience has to include a tour to discover the wines of Tuscany and Chianti area in particular. You will start this phenomenal wine tour in Chianti area with a visit of an impressive castle located in Greve in Chianti, close to Florence and Siena.
The picturesque valley of Val di Greve offers magnificent landscapes and you will be able to admire everything from the beautifully preserved medieval castle. While visiting the vineyards and charming gardens around the castle, you will also arrive in the historical cellars, where you will have the chance to taste three of the best wines produced at this splendid estate. This will be a perfect introduction to the wines of Chianti area, admiring the scenery from the terrace of the cellars and indulging in the delicious wines.

Day 2: Monteriggioni - Siena

The exclusive tour in Chianti wine area will continue after breakfast with a transfer to Monteriggioni, one of the most enchanting towns of Tuscany and Italy, founded in the 13th century and still preserving its medieval center. During this unforgettable visit of Monteriggioni, you will experience life from centuries ago, admiring the small stone houses and narrow streets, surrounded by a strong wall.
Continuing with the Chianti wine experience, you will take a tour of Siena, the beautiful city of Tuscany. You will visit Siena and its most fascinating landmarks, including the Palazzo Publico and its tall Torre del Mangia, overlooking the splendid Piazza del Campo. At the end of the second day, you will have a traditional dinner in a typical restaurant of Castellina in Chianti.

Day 3: San Gimignano – Castellina in Chianti

After breakfast, we continue the wine tour in Chianti area with a visit of San Gimignano, where you can admire the most interesting attractions like the Basilica of Santa Maria Assunta, Palazzo del Popolo or Piazza della Cisterna. After the tour of San Gimignano, you will have a memorable wine tasting in a local farm, further exploring the properties of famous Chianti wines. In the afternoon, you will reach Castellina in Chianti, a charming little town located on top of a hill.
You will discover an authentic destination of Tuscany, with enchanting palaces that were built by important Italian families. In one of these, the Palazzo Squarcialupi, you will visit the Enoteca of Castellina in Chianti, where you can admire the impressive wine collection of over a century, as well as the archive about wine production in Chianti.
This is the perfect ending for a marvelous tour in the Chianti wine area.

  • Greve in Chianti 
  • San Gimignano
  • Monteriggioni 
  • Siena 
  • Castellina in Chianti
  • 2x accommodation in 3-star Hotel with breakfast
  • 1x guided tour of the vineyards
  • 1x guided tour of cellars and renaissance gardens
  • 1x tasting of three wines locally produced
  • Car rental and transfers
  • City tax to pay locally in all the hotels
  • Tips (optional)
Meeting point: 

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


The tour does not include the car rental, neither any transport and travel costs. Therefore, we recommend the use your own vehicle or to rent one.
The wines included in the wine tasting will be the IGT Tuscany, the Chianti Classico and the DOCG Chianti Classico Riserva DOCG, all locally produced, served in the typical cellar located next to vineyards, with panoramic terrace overlooking the valley of Greve.
We guarantee the reservation using only 3-star Hotels or "Agriturismo" at the same price.
Kids under 3 years old travel for free.

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.