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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, Pecorino, and regional specialties on a five-day private-driver tour through the countryside and historic towns.

About this tour

Spend five days following Tuscany’s food and wine traditions, from vineyard tastings to the celebrated cheeses of Pienza. With a private driver and four nights in a 3-star hotel, this independent tour connects Florence, Montepulciano, Pienza, and San Gimignano at a flexible pace.

In Montepulciano, visit a countryside wine cellar for a guided tasting paired with local specialties such as pecorino, cured meats, and bruschetta. Continue through the Val d’Orcia countryside to Pienza, known as the City of Cheese, for a taste of Pecorino Toscano. In San Gimignano, sample wines at a family-owned vineyard, with local produce and handmade pasta dishes. Breakfast, private transportation in an air-conditioned minivan, and hotel or airport pickup and drop-off are included.

This Tuscany food and wine tour offers a relaxed way to explore regional flavors while your driver handles the travel between towns. A private guide and extra touring time can be arranged for an additional fee. Choose this five-day Tuscany food and wine tour for a flavorful introduction to the region’s vineyards, landscapes, and local specialties.

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

  • Private tour
  • Hotel or airport pickup and drop-off
  • 4 nights of accommodation in a standard double room at a 3-star hotel
  • Driver
  • Air-conditioned minivan transport
  • Breakfast
  • Food and drink experiences as specified

Not included

  • Private guide
  • Additional touring time
  • 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 before travel
  • A private guide is available for an additional fee; the listing gives conflicting rates of 60EUR/hour and 90EUR/hour, with a 3-hour daily minimum stated for the latter
  • Additional touring time is available for an extra fee; the listing gives conflicting rates of 60EUR/hour and 90EUR/hour
  • The listing says extra hours and guide fees are payable in cash directly to the driver

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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