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Best price guarantee Learn More
- Gold Operator
- Explore!
- Explorer
- Curated to ignite your sense of adventure
- Group Tour
- Join a group and forge lifelong friendships
- Fully Guided
- An experienced guide will be with you for the entire tour
- Low Intensity
- Travelers can expect some light physical activities
- Guided in English
- Group Size 7 - 16
- Age range 16 to 85
Highlights
- Stroll through vineyards, rolling fields and cypress trees
- Sample some of Italy's finest wines from Chianti to Brunello
- Wander the streets of medieval and renaissance cities
- Enjoy the fresh produce and delicious flavours of Tuscany
Itinerary
- Introduction
- 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
What's Included
- Accommodation
- Guide
- Meals
- Additional Services
- Transport
- Free eSIMTourRadar offers the lead traveler (the person who booked) a free 1GB eSIM for the trip. The eSIM is redeemable only through the TourRadar app 72 hours before departure.
- Optional Extras
What's Not Included
- Flights
- Insurance
- Additional Services
Where You'll Stay
Hotel Bologna
Hotelday 1Hotel Colle Etrusco Salivolpi
HotelDays 2, 3Relais II Chiostro di Pienza Hotel
HotelDays 4, 5, 6Classic Hotel Florence
Hotelday 7Hotel San Giorgio
Hotelday 7
Operated by
Explore!
Number of tours
531
Age Range
16 to 85 years old
Response time
within 1 day
Response rate
92%
Explore is a global adventure travel company with 42 years’ experience in...
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Customer Reviews
- Overall RatingExcellent
- ItineraryExcellent
- GuideExcellent
- TransportExcellent
- AccommodationExcellent
- FoodExcellent
- AJohn· April 30th, 2023Knowledgeable local guide who was extremely helpful and passionate about his home countryShow moreTrip date: April 2023Review collected by Explore!
- AEva· April 30th, 2023Outstanding natural beauty of the region. Pienza, lovely little townShow moreTrip date: April 2023Review collected by Explore!
- AElizabeth· April 30th, 2023All of the landscape and the beautiful sites of Tuscany, together with all the towns that we visited. The wine tasting was that we did on the Monday, together with the additional one that was included because the walking was cut short on the Tuesday were all excellent. We also had an additional, paid for winetasting on Friday which you might want to think about including as well. Perhaps if this is advertised as a walking and wine tour, there should be at least three inclusive wine tastings throughout the week.Show moreTrip date: April 2023Review collected by Explore!
- AKim· May 3rd, 2023So many. Every day provided new highlightsShow moreTrip date: April 2023Review collected by Explore!
- ADavid· May 6th, 2023Walking beautiful countryside. Guide very well informed.Show moreTrip date: April 2023Review collected by Explore!
- AGrace· May 7th, 2023I was happy with all the accomodation, the food was great, Matteo went above and beyond to ensure that everyone had an amazing timeShow moreTrip date: April 2023Review collected by Explore!
- AAndrew· May 28th, 2023The hotels were very nice, especially the one in PienzaShow moreTrip date: May 2023Review collected by Explore!
- AMadison· May 28th, 2023The hotel in Pienza was outstanding!!Show moreTrip date: May 2023Review collected by Explore!
- ASally· May 29th, 2023Siena and the two major walking days - Thursday and Friday - and the excellent meals throughout the week. I think the food was superb.Show moreTrip date: May 2023Review collected by Explore!
- AGill· May 30th, 2023Matthau was an excellent guide Best Insalada Caprese in San Gimignano Best lasagne in Pienza (side street) Best accomodation & breakfast in the Relais in Pienza ( eggs, bacon, cheese, ham, fresh fruit, Nat yogurt & much more) & a luxury to have 3 nights there! All wine experiences great but especially enjoyed Montichiello & their cellars - wine tasting also top notch Great walking and beautiful countryside Enjoyed free time in Sienna & Florence & managed to fit in a visit to Santa Maria Novella (fabulous cloisters and frescos) & the UffiziShow moreTrip date: May 2023Review collected by Explore!
Dates & Availability
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- Instant ConfirmationFrom Sunday31 Aug, 2025To Sunday7 Sep, 2025EnglishThis departure date is available and will 100% departGuaranteed departureMultiple Room TypesFrom:$4,280
- Instant ConfirmationFrom Sunday21 Sep, 2025To Sunday28 Sep, 2025EnglishAlmost Sold OutThis departure date is available and will 100% departGuaranteed departureMultiple Room TypesFrom:$4,610
- Instant ConfirmationFrom Sunday5 Oct, 2025To Sunday12 Oct, 2025EnglishAlmost Sold OutThis departure date is available and will 100% departGuaranteed departureMultiple Room TypesFrom:$4,280
- Instant ConfirmationFrom Sunday12 Apr, 2026To Sunday19 Apr, 2026EnglishThis departure date is available and will 100% departGuaranteed departureMultiple Room TypesFrom:$4,840
- Instant ConfirmationFrom Sunday10 May, 2026To Sunday17 May, 2026EnglishThis departure date is available and will 100% departGuaranteed departureMultiple Room TypesFrom:$4,840
- Instant ConfirmationFrom Sunday24 May, 2026To Sunday31 May, 2026EnglishThis departure date is available and will 100% departGuaranteed departureMultiple Room TypesFrom:$4,840
- Instant ConfirmationFrom Sunday7 Jun, 2026To Sunday14 Jun, 2026EnglishThis departure date is available and will 100% departGuaranteed departureMultiple Room TypesFrom:$4,510
- Instant ConfirmationFrom Sunday6 Sep, 2026To Sunday13 Sep, 2026EnglishThis departure date is available and will 100% departGuaranteed departureMultiple Room TypesFrom:$4,510
- Instant ConfirmationFrom Sunday13 Sep, 2026To Sunday20 Sep, 2026EnglishThis departure date is available and will 100% departGuaranteed departureMultiple Room TypesFrom:$4,840
- Instant ConfirmationFrom Sunday20 Sep, 2026To Sunday27 Sep, 2026EnglishThis departure date is available and will 100% departGuaranteed departureMultiple Room TypesFrom:$4,840
Best price guarantee Learn More
What our customers ask about this tour
The content in our FAQ section is subject to change.- A
Andy
Asked on July 3rd, 2022What is included in the cost and what isn't? I will be traveling by myself and want a single occupancy room. How much extra for that? What are the accommodations
Explore!Operator•Written July 2022The single supplement would be from £270.00 per person.
- L
Liam
Asked on March 15th, 2022What is the 1,460.00 for?
- Explore!Operator•Written March 2022
The 1,460.00 would be the cost of the trip.
- J
Joel
Asked on February 26th, 2022Do not want to miss the walk, and pretty confident we are fit enough to do it. However, we are cautious. What happens if we cannot make the last couple of kilometers? What is Explore's cancellation policy? At what point do you guarantee the trip will happen? Do you transport luggage from hotel to hotel so that we just carry a day pack? What about lunches
- Explore!Operator•Written February 2022
Luggage is transported from hotel to hotel. You will only carry your day bags. If you cancel outside of 60 days before departure you can cancel with either a credit for future tours, or loss of deposit. After 60 days - the cancellation charges then change: 59-42 days before trip start date – 30%, or loss of deposit if higher. 41-28 days before trip start date – 60%. 27-14 days before trip start date – 90%. Less than 14 days before trip start date – 100%. We would need at least 6 passengers to be able to guarantee this departure date. Lunches are usually a packed lunch or arranged on the day at a local restaurant.
- J
James
Asked on January 21st, 2022Are single rooms available?
- Explore!Operator•Written January 2022
Currently there are single rooms available on this trip, and if further people book we can always request further rooms.
Good to Know
Tour ID: 124710
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