Tuscan Wine & City Experience – Siena

3 days

Enjoy a chauffeured wine tour through Tuscany from the historic medieval city of Siena…

Trip Highlights

  • Return flights to Pisa or Florence (no hold luggage included)

  • Three-day car hire package

  • Two nights in a central four-star hotel in the beautiful heart of medieval Siena

  • On your first evening, enjoy a fantastic introduction to the Tuscan wines in a private cellar in a local enoteca

  • Explore in style with a private chauffeured wine tasting tour through the stunning vineyards of Brunello and discover the secrets of Tuscan viticulture

  • Savour local Tuscan food with lunch in the middle of the vineyards

from $1,458 per person

This is a guide price based on two people travelling together and sharing a room. Flights are included with this package.


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Trip details

Day 1

Fly into either Pisa or Florence airport and pick up your hire car before driving to your four-star hotel in Siena. You’ll be whisked off to an authentic local enoteca for your first taste of Tuscan wines alongside local canapés. The perfect pre-dinner Tuscan wine-tasting!

Day 2

Your day starts with a private guided wine experience with an English-speaking driver/guide, including visits and tastings at a selection of boutique wineries around the Chianti Classico or Brunello producing region and a traditional Tuscan lunch with accompanying wine and olive oil tasting. (Our clients often opt to extend this trip to include two days in the vineyards.)

Day 3

The day is yours to explore the city. Why not explore the Gothic architecture of the world’s most unique piazza, Piazza dal Campo in Siena. Return the car to the airport before heading home.

Ready to Plan your Trip?

All of the holidays we create are completely tailor-made to you

This sample itinerary is intended to give you a flavour of what we can do.

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Recent Google Reviews

SmoothRed planned a truly fabulous trip from Paris through Brittany to Normandy and back to Paris. Every part of the trip was wonderful and seamlessly executed. It was a trip of a lifetime! Without any hesitation or qualifications, we heartily recommend SmoothRed. They customized an extraordinary family trip.

Dorothy Weinstein

Very well organised trip to Tuscany, getting in 2 wine regions. Lovely hotel with amazing view. The best part was our guide Paula who ensured our wine tasting tours were with smaller wineries which have authenticity and care for the environment. Highly recommend SmoothRed!

Warren De Villiers

To Adam & the SmoothRed Team. Our recent trip to Bordeaux and the Medoc/St Emillion has been a wonderful trip & experience. One I would have no hesitation in saying is top class. I would certainly use SmoothRed & their travel associates in future wine tasting trips. The entire group…

Paul Green

SmoothRed did an outstanding job providing chauffeured driven wine tour through Bourgogne and the Rhone valley (France). The multiple vendors they used were all Courteous, Prompt, and very fluent in English. This 7 day trip went without problems. I would highly recommend SmoothRed.

Dan Lepley

We came to Bordeaux for part of our honeymoon and took the First Growth Bordeaux tour. SmoothRed worked with us to curate a trip based on our desires. The 8 Chateaux we visited, the 3 delicious lunches, and the hotel were wonderful, but what set the trip apart was our…

Tibita Kaneene

“Thanks for taking the time and trouble to call. You really have set the standard by which we compare all other companies!! Thank you so much for organising a fantastic itinerary with such an interesting and varied range of stop-overs. We are already starting to think about next year’s trip to France so would welcome any suggestions.”

Hilary Alder

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