Cortona Main square
Piazza Grande, Montepulciano
Tuscany countryside
Montepulciano countryside
Pienza Countyside
Medieval Tuscan Village
Cortona, Villa Bramasole
Under the Tuscan Sun Tour from Rome-Cortona & Montepulciano 1 day 8
Chianti Wine cellar
Nobile di Montepulciano
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Under the Tuscan Sun Tour from Rome-Cortona & Montepulciano 1 day

(3)
Rome, Italy
Cultural ToursLuxuryBus & Minivan Tours
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About this activity

Escape Rome for a full day immersed in Tuscany's most photogenic hilltop towns and rolling countryside. This curated journey combines visits to the medieval villages of Cortona and Montepulciano with scenic drives through iconic Tuscan landscapes and tastings of regional wine and food.

This excursion from Rome in one day allows travelers to enjoy some of the most typical features of a region, Tuscany, that is very much beloved by anyone around the world. You will visit medieval villages of amazing beauty, Cortona and Montepulciano. Moreover, you will be driven through breathtaking landscapes, and have the chance to savor the local excellent products, wines, and local food!
Book with no hesitation!

Highlights

  • ✓Explore Cortona, an ancient hilltop town with Renaissance art and winding cobblestone streets
  • ✓Discover Montepulciano, a fortified village famous for Vino Nobile wines
  • ✓Drive through iconic Tuscan hills and cypress-lined valleys
  • ✓Sample local wines and traditional Tuscan cuisine
  • ✓Expert-guided cultural tour covering medieval history and architecture

Insider tips

  • ★Wear comfortable walking shoes—both villages involve steep medieval streets and uneven terrain
  • ★Bring a light layer; hilltop towns can be cooler and windier than Rome, even in summer
  • ★Book wine tastings in advance if you have specific vineyard preferences; timing affects availability

Good to know

  • •10-hour full-day tour departing early from Rome; plan for minimal free time
  • •Includes transportation by minivan/coach; confirm pickup location and time with supplier the day before
  • •Some medieval village areas have limited wheelchair accessibility due to historic cobblestone streets and stairs

Who it's for

Culture and history enthusiasts seeking authentic Tuscan experiencesWine lovers wanting to taste regional Vino Nobile winesPhotographers drawn to medieval architecture and scenic countrysideLuxury travellers preferring guided tours over self-drive exploration

Best time to visit

Late April through October offers the most pleasant weather and clearest views of Tuscan landscapes. Early morning departure maximizes daylight for photography and exploration.

Frequently asked questions

Available
From€1,100
per person