Tuscany Walking and Wine

  • Best price guaranteed
  • No booking fees
5 Based on 1 Review
  • duration 8 days
  • tour type Small group Request as private
  • age requirement 16-95 yrs
  • max group size 16
  • guiding method Fully guided
  • Tour Code BM-17303
  • Footprint Carbonneutral CO2 emissions resulting from all trips on Bookmundi will be offset via investments in carbon reduction projects.
  • Operated in English
  • Starts Pisa, Italy
  • Ends Florence, Italy
HIGHLIGHTS Download trip notes
  • Enjoy short walks in the classic rolling landscapes of southern Tuscany
  • Spend time in historic hill-top towns and cities of Florence and Siena
  • Enjoy wine tastings and delicious Tuscan cuisine
The "Tuscany Walking And Wine" tour starts from Pisa and ends in Florence. It is a walking tour that takes 8 days taking you through Castellina In Chianti, Montalcino, Florence and 5 other destinations in Italy. "Tuscany Walking And Wine" is a guided small group tour that includes accommodation in hotels, 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 and Montalcino

Local cuisine - Enjoy the fresh produce and delicious flavours of Tuscany
  • Day 1 : Trip starts today in Pisa
  • Day 2 : Walk to the hilltop town of San Gimignano; enjoy a wine tasting before driving to Castellina in Chianti
  • Day 3 : Hike along white gravel tracks typical of Tuscany; visit a winery for lunch and a tasting of Chianti wines
  • Day 4 : Visit medieval Siena on market day; drive to Pienza in southern Tuscany
  • Day 5 : Take a panoramic walk from Pienza; optional cheese tasting
  • Day 6 : Hike in the Val D'Orcia from San Quorico D'Orcia to hilltop Montalcino
  • Day 7 : Drive to Florence; orientation walk and free time to explore this fabulous city
  • Day 8 : Trip ends in Florence
  • Hotel Bologna (1 night)
  • Hotel Colle Etrusco Salivolpi (2 nights)
  • Relais II Chiostro di Pienza Hotel (3 nights)
  • Classic Hotel Florence (1 night)
  • 7 Breakfasts, 2 Lunches
  • Minibus
  • Train
  • Explore Tour Leader
  • 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 Tuscany Walking and Wine tour. Travel insurance is mandatory to buy. We recommend purchasing it from World Nomads.
5 - Excellent
Based on 1 review
  • Judith
  • On Jun 10 2020
5 - Excellent
A well paced trip with an excellent guide, I really enjoyed it, despite the covid rules.
REQUEST A PRIVATE, CUSTOMIZABLE DEPARTURE By design, this is a group tour. You can however request a private, customized version of this tour for yourself or your private group of people. Private departures are usually more expensive, but come with these benefits:
  • Personal Itinerary can be tweaked and customized.
  • Protected Travel within your own bubble.
  • Professional Access our Travel Specialists' insider knowledge.
  • Privacy Enjoy a tour focused solely on you or your travel group.
Request a private and/or personalized departure To design a private tour, we'll ask you some more information in the following steps.
Why Book with Bookmundi
What are customers saying about Bookmundi
4.65 Average 664 Reviews
GOOD TO KNOW Download trip notes

No additional cancellation fees apply for this Tuscany Walking and Wine tour. You can cancel the tour up to 63 days prior departure and avoid paying the full amount, but your deposit paid is non-refundable. No refund applies for cancellations within 62 days of departure.


For any tour departures within 29 April 2024, full payment is required. For tours that depart later than 29 April 2024, a deposit of 10% is required to confirm this tour, and the remaining balance will be charged 62 days before trip departure.

Travel Insurance

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 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 traveling to, as part of this itinerary.

For Solo Travelers

A twin share room may not always be available for solo travelers as it depends on the final number of people on the tour. If you have picked twin share room while booking, and that option is not available, we will get back to you after booking. A single room might then be available against an additional fee.

COVID-19 Safety Measures

This trip incorporates the following COVID-19 measures:

  • The average size of this tour is just 12 people.
  • Rigorous hygiene safety measures will be followed in transportation, accommodation and meal venues.
  • All travellers 18 years and older will be required to be either fully vaccinated atleast 14 days prior to departure or have taken a negative test (rapid antigen or PCR)  within 72 hours of departure.
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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