It appears that your web browser does not support JavaScript, or you have temporarily disabled scripting. The Explore website requires JavaScript enabled to operate correctly.

Find a tour

Where would you like to go?
What type of tour do you like?
When would you like to go?
More search options
543 Matching trips
Site Search

Other tours you might like


Discover our latest brochures available online now, with hundreds of adventures to choose from.


Be the first to hear about great new tours, competitions, special offers and unique departures.

Customer Reviews

Average Rating: Red-stars

Total number of reviews: 2,720

Gift Vouchers

The perfect gift idea for any occasion. Send gift vouchers and create fantastic memories with vast tours and experiences to choose from.

Trails of Classic Tuscany LTY

Visiting: Italy
Tour Duration 8 Days

Centre-based Week In Tuscany

Rolling hills, medieval towns and great food are all part of this walking holiday amongst the UNESCO-listed landscapes of southern Tuscany's Val d'Orcia. Based at a comfortable agriturismo surrounded by classic Tuscan countryside, we enjoy walks through sun-drenched fields, along avenues of cypress trees and ancient pilgrimage trails. We also explore the historic hill-top town of Montalcino, Renaissance jewel of Pienza and visit Siena by local train.

Tour Highlights

  • Tuscan Landscapes - Five day walks amongst the iconic UNESCO-listed landscapes of the Val d'Orcia
  • Montalcino - Fabulous hill town where you can sample the famous Brunello wine
  • Pienza - Stroll the streets of this historic Renaissance town
  • Agriturismo - Charming and comfortable accommodation in a stunning rural location


Show more
  • 1
    Join tour Pisa Airport; transfer to Buonconvento

  • 2
    Walk amongst classic Tuscan landscapes along the Via Francigena

  • 3
    Montalcino Walk and visit to Sant Antimo Monastery

  • 4
    Free day to visit Siena by train

  • 5
    Walking in the Tuscan Badlands

  • 6
    Walking from Pienza amongst the cypress tree avenues

  • 7
    Walk from San Qurico D'Orcia

  • 8
    Tour ends Pisa Airport

Tour notes

Each departure date has it's own dedicated tour note, detailing all you need to know about that tour. 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 Trails of Classic Tuscany tour available at present.

Please select a date:

Customer rating:
Trails of Classic Tuscany
4.5 out of 5 based on 9 ratings. Read reviews
Included meals 7 3 4
Breakfast Lunch Dinner
7 nights Standard Hotel
Tour Staff
Explore Tour Leader / Trek Guide
Maximum Altitude on Trek (m)
Group Size
Generally 10 - 16