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Wine Trails of Classic Tuscany LTY

Visiting: Italy
Trip Duration 8 Days

Walking holiday in Tuscany

Rolling hills, medieval hill-top towns and enjoying great food and wine are all part of this walking holiday among the iconic landscapes of southern Tuscany. We ramble through the vineyards of Chianti, along avenues of cypress trees and on ancient pilgrimage trails. We also explore historic Montalcino and Montepulciano, take in the sights of marvellous Siena and soak up the atmosphere of Renaissance Florence.

Tour Highlights

  • Tuscan landscapes - Walks amongst vineyards, rolling fields and avenues of cypress trees
  • Wine tastings - Sample some of Italy's finest wines from Chianti to Brunello
  • Hill-top towns - Discover San Gimignano, Pienza, Montepulciano and Montalcino
  • Siena and Florence - Explore these stunning medieval and renaissance cities
  • Local cuisine - Enjoy the fresh produce and delicious flavours of Tuscany


Itineraries on some departure dates may differ, please select.

Show more
  • 1
    Join trip Pisa airport; drive to Castellina in Chianti

  • 2
    Walk in the heart of Chianti country; wine tasting

  • 3
    Walk to San Gimignano; wine tasting

  • 4
    Visit medieval Siena; drive to Pienza in southern Tuscany

  • 5
    Walk to Montepulciano via Montichiello

  • 6
    Hike in the Val D'Orcia to hill-top Montalcino

  • 7
    Drive to Florence; orientation walk

  • 8
    Trip ends in Florence

Trip notes

Each departure date has its own dedicated trip note, detailing all you need to know about that trip. Whether you've already booked, or weighing up your options, please choose carefully the relevant itinerary for you.

We have the following different versions of the Wine Trails of Classic Tuscany trip available at present.

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Customer rating:
Wine Trails of Classic Tuscany
Included meals 7 2 0
Breakfast Lunch Dinner
Train, Minibus
3 nights Standard Guesthouse
4 nights Standard Hotel
Trip Staff
Explore Tour Leader / Trek Guide
Maximum Altitude on Trek (m)
Group Size
Generally 10 - 16