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Rome Medieval Tuscany Tour with Siena & San Gimignano 4 Days

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  • Rome, Italy
  • 4 days
  • Updated November 2, 2026

Explore Siena, San Gimignano, and other medieval Tuscan towns on a four-day journey from Rome with wine tastings and three hotel nights.

About this tour

Discover Tuscany’s medieval towns on a four-day journey from Rome, with historic streets, hilltop views, and regional wine along the way. This Rome Medieval Tuscany Tour visits Orvieto and its cathedral, then continues to Cortona before exploring Siena and San Gimignano.

Travel by air-conditioned minivan with a local driver-guide, and enjoy three nights of accommodation and Wi-Fi on board. The itinerary also takes in Volterra, a major center of Etruscan history, the Chianti Valley for wine tasting, and the walled town of Lucca. On the final day, explore Pienza, Montepulciano, and Montalcino, known for its fortress and opportunities to taste its red wine, before returning to Rome.

With a small-group format and a mix of celebrated towns and lesser-known stops, this Rome Medieval Tuscany Tour offers a rich introduction to the region. Gather your travel details and get ready to experience Tuscany’s history, landscapes, and flavors.

Highlights

  • Explore Siena, San Gimignano, Volterra, and other medieval Tuscan towns
  • Visit Orvieto Cathedral and Cortona on the way to Siena
  • Taste wines in the Chianti Valley and Montalcino
  • Discover Lucca, Pienza, and Montepulciano
  • Travel between destinations in an air-conditioned minivan

What's included

Included

  • 3 nights of accommodation
  • Free Wi-Fi on board
  • Wine tastings
  • Transport by air-conditioned minivan
  • Local driver-guide
  • Food and drink as specified in the itinerary

Not included

  • Food and drinks not specified in the itinerary
  • Hotel city taxes
  • Gratuities and porterage
  • Hotel pickup and drop-off

Ratings on each provider

The ratings and review counts each booking site shows for this tour.

Important information

  • Moderate physical fitness is recommended
  • Wheelchair accessible
  • A multilingual guide may operate the tour
  • Passport name, number, expiration date, and country are required at booking for all participants
  • At least 2 people are required per booking
  • Meet in the hotel lobby

How this score is calculated

This tour has no TourTruth score yet: Viator doesn't show a usable rating for it. It gets a score as soon as a provider lists one.

How the score works
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  • Listings on different providers are combined in proportion to their review counts.
  • Tours with few reviews are pulled toward the average until more reviews come in, so a handful of perfect reviews can't top the list.
  • The result is shown from 0 to 10. Tours without a usable provider rating are not scored.

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