Tuscany Walks & Chianti Wines

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  • No booking fees
4.7 Based on 38 Reviews
  • duration 8 days
  • tour type Small group Request as private
  • age requirement 18-95 yrs
  • max group size 16
  • guiding method Fully guided
  • Tour Code BM-7835
  • Footprint Carbonneutral CO2 emissions resulting from all trips on Bookmundi will be offset via investments in carbon reduction projects.
  • Operated in English
  • Starts PANCOLE, Italy
  • Ends PANCOLE, Italy
HIGHLIGHTS Download trip notes
  • Walk the classic rolling hills of Tuscany
  • Stay in a family run 3
  • Hotel
  • Enjoy fabulous chianti wines
  • Visit Siena and Florence
Start and end in PANCOLE, the tour "Tuscany Walks & Chianti Wines" is a guided trekking and hiking tour that takes 8 days. You will travel through Siena, Greve In Chianti, PANCOLE and 4 other destinations in Italy. "Tuscany Walks & Chianti Wines" is a small group tour which includes accommodation in hotels, transport, meals and others.

With Renaissance cities, medieval villages and cypress-lined avenues winding through vineyards, southern Tuscany is the perfect place for a relaxing guided walking holiday. Based at the welcoming family-run Hotel Le Renaie, we visit beautiful San Gimignano, Radda in Chianti, the Unesco World Heritage site of Siena and the magnificent city of Florence. During the week, we sample several varieties of the local chianti and learn more about Italian wine on an interactive course at a wine school.

Interested in extending  your adventure?Whether you are looking to ease into your destination at a more leisurely pace or to allow extra time to unwind, consider booking additional nights in Pisa or Florence: Pre-tour package Post-tour package City extension package
Visit the Trip Notes and speak to your sales representative for more details on the packages, including costs, availability, additional activities, and any special arrangements that can be made. All options are subject to availability.

Join us to celebrate Exodus’ 50th anniversary! The departure starting in Pancole on 24 August 2024 features extra inclusions to mark the occasion: a cruise with aperitif along the Arno River in Florence, a local birthday celebration and a special edition Exodus kitbag.

Did you know you can travel by train to this trip? Find out more here
  • Day 1: Start in Pancole
  • Day 2: Walk a section of the Via Francigena; afternoon local wine tasting
  • Day 3: Walk to Radda in Chianti
  • Day 4: Travel to Siena and explore the stunning historic centre; learn about Tuscan and Italian wines at a wine school
  • Day 5: Free day to visit other Chianti villages or relax by the pool
  • Day 6: Discover the magnificent city of Florence
  • Day 7: Walk to picturesque San Gimignano: afternoon wine-tasting
  • Day 8: End in Pancole
  • All accommodation
  • All breakfasts, five dinners, three wine tastings
  • All transport and listed activities
  • Tour leader throughout
  • Travel insurance
  • Single accommodation (available on request)
  • Visas or vaccinations
  • Local taxes (approximately €10 per person, see Trip Notes)
  • Pre & Post Package
  • Extension Package
4.7 - Excellent
Based on 38 reviews
  • Anonymous
  • On Sep 27 2020
5 - Excellent
Fantastic trip - even more appreciated in these times of COVID restrictions!
I travelled solo on this trip departing on 12 Sept 2020, having booked it quite late as Italy was one of the few venues Brits could travel to without any COVID-related quarantine requirements either end. I was not disappointed. ... Read more
  • Anonymous
  • On Jul 07 2019
5 - Excellent
A fabulous combination of walking the Tuscan countryside, combined with wine tastings and city visits. Alejandro was a brilliant leader. Villa Castalta is a perfectly adequate base for a walking holiday. The meals at the Villa... Read more
  • Anonymous
  • On Jul 03 2019
5 - Excellent
One of the best...
For me, there are three criteria that make a great trip by this operator: the members of the group, the leader, and the location/activities. The members of the group on this trip were wonderful: great company, entertaining, and... Read more
  • Anonymous
  • On Jun 22 2019
5 - Excellent
Excellent trip - But a bit more than gentle walking
We had a great of walking and wine tasting in the Chianti region with our excellent guide Alejandro. Our accommodation at Villa Castela was probably the best we have enjoyed with this tour company - great location, tranquil,... Read more
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.
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GOOD TO KNOW Download trip notes

No additional cancellation fees apply for this Tuscany Walks & Chianti Wines tour. You can cancel the tour up to 93 days prior departure and avoid paying the full amount, but your deposit paid is non-refundable. No refund applies for cancellations within 92 days of departure.


For any tour departures within 28 May 2024, full payment is required. For tours that depart later than 28 May 2024, a deposit of 25% is required to confirm this tour, and the remaining balance will be charged 92 days before trip departure.

Travel Insurance

Tuscany Walks & Chianti Wines 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 Walks & Chianti Wines 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.

COVID-19 Safety Measures

This trip incorporates the following COVID-19 measures:

  • This tour has received the World Travel and Tourism Council’s ‘Safe Travels’ stamp, which provides travellers with assurance that COVID-19 health and hygiene protocols have been adhered to.
  • Group sizes are kept small to maintain a low risk ‘small group bubble’, with an average of 10 guests in each group.
  • Hygiene safety measures and distancing will be followed in transportation, accommodation and meal venues.
  • Several COVID-19 distancing measures have been adopted on this package tour to keep travellers safe.
  • All travellers will be required to be fully vaccinated no less than two weeks prior to travel.
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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