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7 Days & 6 Nights
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Chianti In Style

  • Walk on Tuscany's Chianti Classico wine routes
  • Outstanding 4* & 5* hotels in exquisite locations
  • Chianti wine tour and tasting at one of the finest vineyards in the region
  • Enter the glorious medieval city of Siena on foot, a Gothic open-air museum
  • Sample Tuscan flavours during dinner at a Michelin star restaurant
Walk Tuscan wine trails through the timeless landscapes of Chianti to Siena, staying in ‘In Style’ accommodation. This very special tour combines walking with opportunities to eat authentic Tuscan cuisine at a Michelin star restaurant, tour a vineyard and of course sample the world-renowned wines, and stay in the outstanding hotels. An intoxicating mix of exceptional experiences. This alluring region has been producing world-famous velvety red wines since the 13th century. Situated between Florence and Siena, Chianti, is formed of castles, fortresses, Romanesque churches, olive groves, and row upon row of vines, interspersed with pretty wooded valleys.


Day 1 Arrive in Siena; transfer to Gaiole in Chianti Day 2 Transfer to Radda; walk back to Gaiole in Chianti via Vertine 9 miles / 14 km Day 3 Gaiole in Chianti Loop Walk via Badia a Coltibuono Monastery & Riecine Winery 9 miles / 15 km Day 4 Walk to Hotel Le Fontanelle, near Pianella 11 miles / 18 km Day 5 Free day at Hotel Le Fontanelle Day 6 Walk to Siena 9 miles / 15 km Day 7 Onward travel from Siena

This trip has a carbon score of 6kg per person per night, meaning it’s one of our best trips! For comparison, a carbon count of 6kg is equivalent to 4.5 ham and cheese sandwiches from the store. Here at Macs, we pride ourselves on being a responsible travel company and continue to adopt, develop and innovate ways to positively impact the environment. Find out more information on how we've carbon counted our trips.


Other Information

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  • Chianti In Style
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Reasons to believe in Macs Adventure:
The Biggest Choice

The Biggest Choice

Self-guided walking & cycling is all we do - we have over 500 tried & tested trips.
Our Heritage

Around Since 2003

We’re still founder led & the world’s number one self-guided operator with mountains of experience.

21,000+ Customer Reviews

Plus, with a Feefo Platinum Service Award & British Travel Awards, you know you're in good hands.
Positive Impact

Positive Impact

We use independent suppliers to support communities along our routes, as well as work with organisations to help maintain & restore paths.
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