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Tuscany Food and Wine Tour 5 Days

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

Taste Tuscan wines and regional specialties on a five-day private-driver journey through Montepulciano, Pienza, and San Gimignano.

About this tour

Savor Tuscany through its wines, regional specialties, and storybook countryside on a five-day private-driver tour. This Tuscany Food and Wine Tour visits Florence, Montepulciano, Pienza, and San Gimignano, pairing time in celebrated towns with tastings rooted in local traditions.

In Montepulciano, visit a countryside wine cellar for a guided tasting alongside pecorino cheese, cured meats, and bruschetta, and learn about traditional winemaking. In Pienza, known as the City of Cheese, sample Pecorino Toscano before taking in views across the Val d'Orcia. At a family-owned vineyard in San Gimignano, taste local wine and produce, with handmade pasta dishes also featured. A private driver and air-conditioned minivan make it easy to move between these distinct Tuscan settings, while four nights of accommodation are included. A licensed guide is available for an additional fee.

Choose this Tuscany Food and Wine Tour for a flavorful introduction to the region, from cellar tastings to scenic country roads. Book your five-day escape and experience Tuscany one glass and local specialty at a time.

Highlights

  • Taste wines and local specialties at a Montepulciano countryside cellar
  • Sample Pecorino Toscano in Pienza, the City of Cheese
  • Enjoy wine and local produce at a family-owned San Gimignano vineyard
  • Travel between Tuscan towns with a private driver

What's included

Included

  • Hotel or airport pickup and drop-off
  • Private tour
  • 4 nights of accommodation in a standard double room at a 3-star hotel
  • Driver
  • Air-conditioned minivan transportation
  • Food and drink experiences in Montepulciano, Pienza, and San Gimignano

Not included

  • Private guide: 80 EUR per hour
  • Additional touring time: 80 EUR per hour
  • Excess luggage charges, where applicable
  • Food and drinks unless specified
  • Gratuities

Ratings on each provider

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

Important information

  • Suitable for all physical fitness levels
  • Each traveler may bring 1 suitcase and 1 carry-on bag
  • Oversized or excess luggage may be restricted; check with the operator in advance
  • A guide can be added for 90 EUR per hour, with a 3-hour daily minimum; pay the driver in cash
  • Extra itinerary time can be added for 90 EUR per hour; pay the driver in cash

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
  • Each provider rating is turned into a percentile: the share of that provider's ratings it beats, weighted by review counts.
  • 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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