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Tuscany Wine and Cooking Tour 5 Days

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

Explore Florence, Montepulciano, San Gimignano, and Pienza on a five-day private Tuscany journey with four nights in Siena.

About this tour

Spend five days tracing Tuscany’s sunlit landscapes, historic towns, and food culture on a private journey from Rome. With a driver handling the road, you can focus on the scenery and the character of each stop.

The itinerary includes Florence, Montepulciano, San Gimignano, and Pienza, with four nights based in Siena at a 3-star hotel. Travel in an air-conditioned minivan and enjoy the flexibility of a private tour. A licensed local guide can be arranged for visits at an additional cost, offering deeper context along the way. Pickup and drop-off are available at your hotel or the airport, and an infant seat can be requested.

This Tuscany wine and cooking tour pairs independent exploration with the ease of private transport. Confirm any oversized luggage with the operator before departure, then set out to discover the towns and landscapes that make Tuscany memorable.

Highlights

  • Explore Florence, Montepulciano, San Gimignano, and Pienza
  • Settle into Siena for four nights
  • Travel through Tuscany with a private driver
  • Request a licensed local guide for visits

What's included

Included

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

Not included

  • Private guide: 60 EUR per hour, minimum 3 hours, paid in cash to the driver
  • Additional touring time: 50 EUR per hour, paid in cash to the driver
  • 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
  • One infant seat available on request
  • Maximum luggage allowance: one suitcase and one carry-on bag per traveler
  • Oversized or excess luggage may be restricted; check with the operator before travel
  • The tour starts in Rome and includes four nights in Siena

Frequently asked questions

Where does the tour start?

The tour starts in Rome and includes hotel or airport pickup and drop-off.

Where will I stay?

The itinerary includes four nights in a standard double room at a 3-star hotel in Siena.

Can I add a tour guide?

A licensed local guide can be requested for 60 EUR per hour, with a 3-hour minimum. Pay the driver in cash.

Can I extend the touring time?

Additional touring time is available for 50 EUR per hour, payable in cash directly to the driver.

What luggage can I bring?

Each traveler may bring one suitcase and one carry-on bag. Ask the operator in advance about oversized or excess luggage.

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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