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Tuscany Food and Wine Tour 5 Days

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

Explore Tuscany’s food and wine with a private driver, tasting local specialties in Montepulciano, Pienza, and San Gimignano.

About this tour

Discover Tuscany through its celebrated wines, regional dishes, and historic towns on a five-day independent journey with a private driver. This Tuscany Food and Wine Tour visits Florence, Montepulciano, Pienza, and San Gimignano, pairing flexible travel with memorable local tastings.

In Montepulciano, visit a countryside wine cellar for a guided tasting alongside pecorino cheese, cured meats, and bruschetta, with an introduction to traditional winemaking. Continue to Pienza, known as the City of Cheese, to taste Pecorino Toscano and take in views across the Val d'Orcia countryside. In San Gimignano, sample wines at a family-owned vineyard, accompanied by local produce and handmade pasta dishes. Florence adds another distinctive stop to the route.

A private driver makes it easier to move between these Tuscan destinations at your own pace. Accommodation is in a standard double room at a 3-star hotel, and breakfast is included. A licensed guide can be added for an extra charge. Choose this Tuscany Food and Wine Tour for a flavorful way to experience the region’s towns, landscapes, and food traditions.

Highlights

  • Taste wines and local specialties in 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

  • Food and drink
  • Private tour
  • Breakfast

Not included

  • 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
  • Accommodation is a standard double room in a 3-star hotel
  • A maximum of 2 bags per person is allowed: 1 suitcase and 1 carry-on
  • Oversized or excess luggage may be restricted; check with the operator before travel
  • Extra itinerary time costs 90 EUR per hour, payable in cash directly to the driver
  • An optional guide costs 90 EUR per hour, with a 3-hour daily minimum; pay in cash directly to the guide

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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  • 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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