Southern Tuscany Walking and Wine

  • Best price guaranteed
  • No booking fees
  • duration 8 days
  • tour type Group
  • age requirement 14+ yrs
  • guiding method Live Guide/Instructor
  • Starts Pisa, Italy
  • Ends Florence, Italy
HIGHLIGHTS Download trip brochure
  • 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
  • Hilltop towns Discover San Gimignano, Pienza, Montepulciano and Montalcino
  • Siena and Florence Explore these stunning medieval and renaissance cities
The trip Southern Tuscany Walking And Wine starts in Pisa and ends in Florence. It is a walking trip that takes 8 days taking you through San Quirico d'Orcia, Volpaia, Montepulciano and 8 other destinations in Italy. Southern Tuscany Walking And Wine is a guided small group trip that includes accommodation, transport, meals and others.

A walking holiday that takes in the splendours of southern Tuscany, an iconic landscape of a rolling hills, avenues of cypress trees and medieval hilltop towns. Ramble through the vineyards of Chianti, along ancient pilgrimage trails and explore the captivating cities of Siena and Florence. Wine tastings - Sample some of Italy's finest wines from Chianti to Brunello Hilltop towns - Discover San Gimignano, Pienza, Montepulciano and Montalcino Local cuisine - Enjoy the fresh produce and delicious flavours of Tuscany
4.5 - Excellent
Based on 177 reviews
Gill's review for another Explore tour
4 - Very Good
  • Gill
  • On Dec 04 2019
“Very Good”
Joanne's review for another Explore tour
5 - Excellent
  • Joanne
  • On Jan 05 2020
“This was our first trip with Explore - and indeed our first Group trip. Everything was amazing. The amount of cycling was perfect, rest stops, support teams, photo opportunities, planning.....everything.
A group of four people is a little 'intense' however on the whole we navigated the relationships well within the group.
One of the highlights for us was Binh himself. He was such an amazing Guide/Tour Leader - words don't really convey how important he was to our enjoyment of the experience. For us, his personal stories made Vietnam's history come alive, and yet he took care to convey many perspectives on the recent history of the country and people. We were able to meet his parents and visit his home which was really a very special moment.
Binh is a real asset to Explore. He is articulate, skilled, very caring and respectful - to the people of Vietnam, to the tour participants and support teams, and to the organisation Explore. With development and growth opportunities he could go very far as a mentor and leader in the company and in the tour industry.”
Derek's review for another Explore tour
4 - Very Good
  • Derek
  • On Jan 13 2020
Select Tour Version:
  • Day 1 : Join trip Pisa airport; drive to Castellina in Chianti
  • Day 2 : Walk in the heart of Chianti country
  • Day 3 : Walk to San Gimignano; wine tasting
  • Day 4 : Visit medieval Siena; drive to Pienza in southern Tuscany
  • Day 5 : Walk to Montepulciano via Montichiello
  • Day 6 : Hike in the Val D'Orcia to hill-top Montalcino
  • Day 7 : Drive to Florence; orientation walk
  • Day 8 : Trip ends in Florence
  • 7 Breakfast, 2 Lunch
  • Minibus, Train
  • Explore Tour Leader / Trek Guide
  • Any international flights to Pisa and from Florence are not included in this price. We always recommend that you arrive 1 day prior to your tour starting date.
  • Travel insurance is not included in this Southern Tuscany Walking and Wine tour. Travel insurance is mandatory to buy. We recommend purchasing it from World Nomads.
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No additional cancellation fees apply for this Southern Tuscany Walking and Wine tour. You can cancel the tour up to 60 days prior departure and avoid paying the full amount, but your deposit paid is non-refundable. No refund applies for cancellations within 59 days of departure.


A deposit of 133 USD is required to confirm this tour. The remaining balance will be charged 59 days before departure. For any departures within 09 October 2020 full payment is required.

Travel Insurance

Southern Tuscany Walking and Wine tour requires that you have adequate and valid travel insurance covering medical and personal accidents, including repatriation costs and emergency evacuation. We recommend using World Nomads' travel insurance.


For this Southern Tuscany Walking and Wine tour getting the required visa(s) is the responsibility for each individual traveller, as visa requirements vary depending on your nationality. We recommend to check with your local embassies representing the countries that you are travelling to, as part of this itinerary.

If you have any question about this tour or need help with planning a trip, please do not hesitate to get in touch with us. We're ready to help.
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