3 Days Tuscan Countryside and Wine Tour: Chianti and San Gimignano, Bolgheri and Scansano, Montalcino and Montepulciano

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Would you like to spend some days in the Tuscan countryside enjoying beautiful views, historical sights, good food…and…Special Wines? Choose this customizable multiple days private tour that will bring you around the Tuscan Countryside and the coast.

You will visit medieval towns, nice country villages, vineyards. You will be surrounded by history and nature with some time for shopping of Italian best goods. We will start from your accommodation and drive you discovering the Chianti area and the medieval village of San Gimignano.

The second day we will drive you through the hills of Volterra and we will reach the Mediterranean see to discovery the village of Bolgheri and its famous Supertuscan wines based on Merlot grape grown up on sandy soils and exposed to the hot sun of the south part of Tuscany and cooled down by the salty sea winds. We will end up in Scansano near the Natural sea reserve and Regional Park of Maremma south of Grosseto province,  a real enchanting wild area of Tuscany,  where you will discover Morellino di Scansano wine, made out of San Giovese grape.

The third day we will drive to the heart of Tuscan land, the south province of Siena to discover two of our most famous wine the Brunello di Montalcino and the Vino Nobile di Montepulciano. You will discover the Val’ d’Orcia, its medieval towns of Montepulciano and Montalcino, its clay hills cultivated in wheat, vineyards and olive grows.

We will plan your private tour discussing the details with you in advance.

We will reserve wine tastings in each wine areas, we will customize your itinerary discussing your needs, we will reserve the accommodations based on your preferences.


Available: All year round, rain or shine

Duration: 3 full days up to 8 hours, but customizable to more than 3 or to more than 8 hours.

All drivers/guides are Tuscan locals

All tours can be customized according to your interests and/or timetable

Tours in Tuscany can make suggestions for a personalized itinerary based on your preferences.

Quotes for tour will be personalized according to your needs, timetable, group size, etc.

Wineries – Boutique family owned wineries, well rated internationally and out of mass tourism. Note we can also check availability to visit wineries suggested by you.


Wines tasted

Reds: Chianti Classico Riserva (Sangiovese grape, blended with local grapes aged 24 to 36 months) Chianti Classico ( Sangiovese grape blended with local grapes, aged up to 24 months).

Vino Nobile di Montepulciano, Riserva di Vino Nobile di Montepulciano (Sangiovese grape, variety Prugnolo Genitle blended with other local red grape).

Brunello di Montalcino, Riserva di Brunello di Montalcino (100% Sangiovese, variety Sangiovese Grosso), Rosso di Montepulciano, Rosso di Montalcino.

Morellino di Scansano (Sangiovese grape blended with local grapes)


Whites: Vernaccia di San Gimignano (Vernaccia Grape 100%), Vermentino Toscana IGT (Vermentino grape)


Olive oil Tasting: Extravirgin Olive Oil Toscano DOP and IGP


Possibility to ship wine and/or olive oil, door to door, directly from the wineries.



  • Luxury, air-conditioned vehicle
  • Pick up and drop off at your accommodation
  • English-speaking driver at disposal all day
  • All local taxes, gasoline, highway/parking tolls, and driver's meal



  • Lunch
  • Wine tasting fees
  • Admission fees where required unless otherwise specified
  • Guide inside of official tourist sites such as museums and churches



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