Southern Tuscany Walking and Wine

  • Best price guaranteed
  • No booking fees
5.0 Based on 1 Review
  • COVID-19protected
  • Wine tasting tour
  • Walking tour
  • Natural landmarks sightseeing
  • Cultural, religious and historic sites
See Itinerary
  • duration 8 days
  • tour type Group
  • age requirement 14+ yrs
  • max group size 17
  • guiding method Live Guide/Instructor
  • Starts Pisa, Italy
  • Ends Florence, Italy
HIGHLIGHTS Download trip notes
  • 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
Start in Pisa and end in Florence, the tour Southern Tuscany Walking And Wine is a guided walking trip that takes 8 days. You will travel through Florence, Castellina In Chianti, Pienza and 5 other destinations in Italy. Southern Tuscany Walking And Wine is a small group tour which 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
5 - Excellent
Based on 1 review
5 - Excellent
  • Judith
  • On Jun 10 2020
“A well paced trip with an excellent guide, I really enjoyed it, despite the covid rules.”
Select Tour Version:
  • Day 1 : Trip starts today in Pisa
  • Day 2 : Walk to San Gimignano; wine tasting
  • Day 3 : Walk in the heart of Chianti country
  • 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 Breakfasts, 2 Lunches
  • Royal Victoria Hotel (1 night)
  • Villa Cristina (2 nights)
  • Relais II Chiostro di Pienza Hotel (3 nights)
  • Classic Hotel Florence (1 night)
  • 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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GOOD TO KNOW Download trip notes

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.


For any tour departures within 13 July 2021, full payment is required. For tours that depart later than 13 July 2021, a deposit of 10% is required to confirm this tour, and the remaining balance will be charged 59 days before trip departure.

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.

COVID-19 Safety Measures

This trip incorporates the following COVID-19 measures:

  • The average size of this tour is just 12 people.
  • Wearing a mask, hand washing and sanitizing has been implemented on this tour. Frequently touched surfaces are regularly disinfected. Hygiene safety measures and distancing will furthermore be followed in transportation, accommodation and meal venues.
  • Various COVID-19 distancing measures have been implemented on this trip to ensure the safety of each traveller.
  • This tour has implemented COVID-19 protocols that are guided by the WTTC (World Travel & Tourism Council), UNWTO (World Tourism Organisation), the European Commission and local government regulations. It amongst others take into account personal protection, extensive disinfecting and social distancing measures.
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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