Tuscany Wine Tour - Discovering Siena and Chianti

5 days

Enjoy a chauffeured wine tour through Tuscany from the historic medieval city of Siena to the magical oasis in the Chianti countryside.

Trip Highlights

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

  • Five-day car hire package (option for private transfers on request)

  • 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

  • Stay in a luxury five-star magical oasis in the Tuscan countryside

  • 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 $2,189 per person

This is a guide price based on 2 people travelling together, in double/twin room occupancy. Use this itinerary to inspire your bespoke Tuscany wine tour.

Enquire online now

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. The perfect pre-dinner Tuscan wine-tasting!

Day 2

A day at leisure to explore the city of Siena.  Learn the historical traditions behind the famous Palio, or why not explore the Gothic architecture of the world’s most unique piazza, sip an espresso in Piazza del Campo, or if you are feeling energetic climb the 14th-century Torre del Mangia with spectacular panoramic city views.


Day 3

Self drive into the heart of the Chianti Classico producing region. Enjoy elegant accommodation in a magical oasis in the Chianti countryside, perched on a hilltop encircled by vineyards. Unwind by the pool, or spend the afternoon immersed in the countryside using complimentary bikes, take the paths through the grounds and into the surrounding hills, we can also prepare a picnic for you to enjoy along the way!

Day 4

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 producing region and a traditional Tuscan lunch with accompanying wine and olive oil tastings. In the early evening a chance to unwind in the spa,  a complete wellness range with heated indoor pool, jacuzzi, sauna, Turkish bath.

Day 5

Wake up and enjoy breakfast with the fabulous Tuscan hills from the panoramic restaurant. After breakfast the countryside is yours to explore, or perhaps visit the city of Florence before travelling back to the airport.

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.

Enquire Now +44 (0) 20 8877 4940

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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    Start creating your tailor made wine-tasting tour today.
    Call our team on +44 (0)20 8877 4940

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