My niece and I are looking for assistance in hotels, hot air balloons ride, Food making class, winery tours in Tuscany. The Cianti Festival is happening during this time frame and we would like to go to that. We want to spend time in San Gamignano, Sienna, Pazano and maybe further east.

We do not offer any custom tour packages nor do we offer assistance in booking just hotels and day tours. We do offer our packages as is.

Could you please advise the demographics for this trip? I'm 37 so not wanting to be with too many older folk or couples.

Generally our demographic leans more towards the 50+ range for a tour like this one but in saying that we have been getting a lot more mixed age groups of late!

What 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

The single supplement would be from £270.00 per person.

What is the 1,460.00 for?

The 1,460.00 would be the cost of the trip.

Do 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

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.

Are single rooms available?

Currently there are single rooms available on this trip, and if further people book we can always request further rooms.

From

$2,870

US $2,600 per person

Tuscany Walking and Wine

8 days

•

From Pisa to Florence

4.6

24 traveler reviews

View all
Best lasagne in Pienza (side street). All wine experiences great but especially enjoyed Montichiello & their cellars.
G
Gill, traveled in May
4.7
View all

From

$2,870

-9%

US $2,600 per person

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

Select Date

1 Adult2 Adults, 1 Child2 Children

Best price guarantee Learn More

Plan your adventure:

Platinum 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
Medium Intensity: Travelers should be comfortable with somewhat-demanding activities
Guided in English
Group Size 7 - 16
Ages 16+

Image of a map showing the route of the tour

Itinerary

Day 1
Pisa
Start point
Piazzale D'ascanio, 1, 56121 Pisa PI, Italy (Pisa Airport, Arrivals Hall, 18:30)
Accommodation
Hotel (Hotel Bologna), Hotel (Hotel Bologna (or similar))
Optional Activities
- Climb Pisa's Leaning Tower
- Explore Pisa in depth
Landmarks
Leaning Tower of Pisa
Campo del Miracoli
Day 2
San Gimignano - Castellina in Chianti
Meals
Breakfast
Accommodation
Hotel (Hotel Colle Etrusco Salivolpi), Hotel (Hotel Colle Etrusco Salivolpi (or similar))
Included Activities
- Hike along the Via Francigena to San Gimignano
- Explore San Gimignano medieval hilltop town
- Wine tasting at Sovestro winery
Optional Activities
- Climb Torre Grossa (tallest tower in San Gimignano)
- Visit the Duomo
- Lunch at cafes in San Gimignano
Landmarks
San Gimignano
Torre Grossa
Sovestro winery
Castellina in Chianti
Day 3
Castellina in Chianti
Meals
Breakfast, Lunch (Light lunch of local cheeses and cold cuts at Castello La Leccia winery)
Accommodation
Hotel (Hotel Colle Etrusco Salivolpi), Hotel (Hotel Colle Etrusco Salivolpi (or similar))
Included Activities
- Guided hike through Tuscan countryside south of Castellina
- Wine tasting at Castello La Leccia winery
- Light lunch of local cheeses and cold cuts
Optional Activities
- Explore the village of Castellina
- Enjoy espresso or aperitivo at a pavement cafe
- Relax at hotel garden and swimming pool
Landmarks
Castello La Leccia Winery
Day 4
Pienza
Meals
Breakfast
Accommodation
Hotel (Relais II Chiostro di Pienza Hotel), Hotel (Relais II Chiostro di Pienza Hotel (or similar))
Included Activities
- Explore Siena medieval city
Optional Activities
- Visit Siena Wednesday market
- Explore Piazza del Campo
- Climb Torre del Mangia bell tower
- Visit Siena Duomo
Landmarks
Siena
Piazza del Campo
Torre del Mangia
Siena Duomo
Pienza
Day 5
Pienza
Meals
Breakfast
Accommodation
Hotel (Relais II Chiostro di Pienza Hotel), Hotel (Relais II Chiostro di Pienza Hotel (or similar))
Included Activities
- Guided 'Gladiator hike' through countryside around Pienza
Optional Activities
- Pecorino cheese tasting at Armellini family's cheese shop in Pienza
Landmarks
Vitaleta Chapel
Day 6
San Quirico d'Orcia to Montalcino
Meals
Lunch (Picnic lunch along the trail)
Accommodation
Hotel (Relais II Chiostro di Pienza Hotel (or similar))
Included Activities
- Explore San Quirico d'Orcia
- Hike through Val d'Orcia
- Picnic lunch along the trail
Optional Activities
- Wine tasting of Brunello di Montalcino
Landmarks
San Quirico d'Orcia
Val d'Orcia
Montalcino
Day 7
Montalcino to Florence
Meals
Breakfast
Accommodation
Hotel (Classic Hotel Florence), Hotel (Hotel San Giorgio (or similar))
Included Activities
- Orientation walk in Florence with tour leader
- View Ponte Vecchio
- View Cathedral of Santa Maria del Fiore
Optional Activities
- Walk up to Piazzale Michelangelo for city views
- Further exploration of Florence
Landmarks
Ponte Vecchio
Cathedral of Santa Maria del Fiore
Piazzale Michelangelo
Day 8
Depart Florence
End point
Viale Machiavelli 25 50125 Firenze, Italy (Classic Hotel Florence, Hotel reception, 09:00)
Meals
Breakfast

Landmarks
Leaning Tower of Pisa
Campo del Miracoli

Landmarks
San Gimignano
Torre Grossa
Sovestro winery
Castellina in Chianti

Landmarks
Castello La Leccia Winery

Landmarks
Siena
Piazza del Campo
Torre del Mangia
Siena Duomo
Pienza

Landmarks
Vitaleta Chapel

Landmarks
San Quirico d'Orcia
Val d'Orcia
Montalcino

Landmarks
Ponte Vecchio
Cathedral of Santa Maria del Fiore
Piazzale Michelangelo

What's Included

Expand All

Accommodation
Guide
Meals
Additional Services
Transport
Optional Extras

What's Not Included

Flights
Insurance
Additional Services

Where You'll Stay

All accommodations are subject to change

Hotel Bologna
Hotel
day 1
Hotel Bologna (or similar)
Hotel
day 1
Hotel Colle Etrusco Salivolpi (or similar)
Hotel
Days 2, 3
Hotel Colle Etrusco Salivolpi
Hotel
Days 2, 3
Relais II Chiostro di Pienza Hotel (or similar)
Hotel
Days 4, 5, 6
Relais II Chiostro di Pienza Hotel
Hotel
Days 4, 5
Hotel San Giorgio (or similar)
Hotel
day 7
Classic Hotel Florence
Hotel
day 7

Operated by

Explore!

Platinum Operator

Rating: 4.5(8,639 reviews)
Response time: within 1 day
Response rate: 100%
Cancellation policy

Traveler Reviews

4.6

Overall rating based on 24 Reviews

Itinerary
4.6
Transport
4.9
Guide
4.9
Accommodation
4.1
Food
4.2
Tour Operator
4.5

Silvana
October 14th, 2025
For the most part it was well planned and the walks and accommodations were good. The last night in Florence the...
Show more
Traveled in October 2025
Reply from: Explore!
Thank you for taking the time to write us a four star review! We are so glad to see you enjoyed the walks exploring this beautiful region of Italy, and that most of the accommodations added to your experience. We do select our hotels based on location and authenticity and I apologise if the standards at the last hotel on your trip did not meet the expectations for this adventure. I have passed your feedback on to our Local Partners to monitor for the future and see if any changes are required. Thank you again for taking the time to send us your thoughts, as it is the only way for us to ensure that our trips are running to the high standard which we would expect. Hopefully we see you on another Explore adventure again soon!
Show more
Cynthia
October 14th, 2025
The description of the walk should have been more clear. This was not a match to the description of the hiking.
Traveled in October 2025
Reply from: Explore!
Thank you for taking the time to share your feedback with us. Although, I am sorry to hear that you felt disappointed with the description of the walks on this trip. We do our best to provide clear and detailed information in our Trip Notes, including walking times, distances, and terrain, so our customers know what to expect for each trip. We also have a specific section “Is This Trip for You” section to help customers assess whether the trip matches their expectations and abilities. That said, we appreciate your comments and I have passed this on to the Product Manager to see if we can make any improvements on the communication on this trip. Thank you again for your comments and we look forward to welcoming you on to another trip in the future.
Show more
P
Philip
October 5th, 2025
The trip was enjoyable, however the group had a fairly large mix of hiking abilities making the hiking portions a bit...
The trip was enjoyable, however the group had a fairly large mix of hiking abilities making the hiking portions a bit on the slow side. The accommodations were good, but the standout was our guide, Enrico who was excellent. While this was his first time guiding this particular tour, he did a fantastic job making sure everyone's needs were met and we got the most out of what the tour has to offer.Show more
Traveled in September 2025
Reply from: Explore!
Thank you for taking the time to share your feedback with us. We’re glad to hear you enjoyed your trip and that you found the overall experience positive. It’s especially great to hear that Enrico made such a strong impression, we will be sure to pass your kind comments on to him. We appreciate your comments about the range of hiking abilities within the group this has been noted and shared with out Product Manager. Thank you again for travelling with us, and we hope to welcome you on another adventure soon.
Show more
A
John
April 30th, 2023
Knowledgeable local guide who was extremely helpful and passionate about his home country
Traveled in April 2023
Review collected by Explore!
A
Eva
April 30th, 2023
Outstanding natural beauty of the region. Pienza, lovely little town
Traveled in April 2023
Review collected by Explore!
A
Elizabeth
April 30th, 2023
All of the landscape and the beautiful sites of Tuscany, together with all the towns that we visited. The wine...
All 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 more
Traveled in April 2023
Review collected by Explore!
A
Kim
May 3rd, 2023
So many. Every day provided new highlights
Traveled in April 2023
Review collected by Explore!
A
David
May 6th, 2023
Walking beautiful countryside. Guide very well informed.
Traveled in April 2023
Review collected by Explore!
A
Grace
May 7th, 2023
I was happy with all the accomodation, the food was great, Matteo went above and beyond to ensure that everyone had...
Show more
Traveled in April 2023
Review collected by Explore!
A
Andrew
May 28th, 2023
The hotels were very nice, especially the one in Pienza
Traveled in May 2023
Review collected by Explore!

Dates & Availability

Select departure month and travellers

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1 Adult2 Adults, 1 Child2 Children

Upcoming departures

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Ends on 6 May, 2026

From Sunday
10 May, 2026
To Sunday
17 May, 2026
This departure date is not available or sold out
Sold out
From:
US $2,600 per person
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From Sunday
24 May, 2026
To Sunday
31 May, 2026
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$2,870
US $2,600 per person
Multiple Room Types
-7%
From Sunday
7 Jun, 2026
To Sunday
14 Jun, 2026
English
Filling Fast
This departure date is available and will 100% depart
Guaranteed departure
From:
$2,870
US $2,670 per person
Multiple Room Types
Instant Confirmation
From Sunday
6 Sep, 2026
To Sunday
13 Sep, 2026
English
Filling Fast
This departure date is available and will 100% depart
Guaranteed departure
From:
US $3,040 per person
Multiple Room Types
Instant Confirmation
From Sunday
13 Sep, 2026
To Sunday
20 Sep, 2026
English
This departure date is available and will 100% depart
Guaranteed departure
From:
US $3,040 per person
Multiple Room Types
From Sunday
20 Sep, 2026
To Sunday
27 Sep, 2026
English
Almost Sold Out
This departure date is available and will 100% depart
Guaranteed departure
From:
US $3,010 per person
Multiple Room Types
From Sunday
4 Oct, 2026
To Sunday
11 Oct, 2026
English
Almost Sold Out
This departure date is available and will 100% depart
Guaranteed departure
From:
US $2,870 per person
Multiple Room Types
Instant Confirmation
From Sunday
11 Apr, 2027
To Sunday
18 Apr, 2027
English
This departure date is available and will 100% depart
Guaranteed departure
From:
US $2,900 per person
Multiple Room Types
Instant Confirmation
From Sunday
9 May, 2027
To Sunday
16 May, 2027
English
This departure date is available and will 100% depart
Guaranteed departure
From:
US $2,900 per person
Multiple Room Types
Instant Confirmation
From Sunday
23 May, 2027
To Sunday
30 May, 2027
English
This departure date is available and will 100% depart
Guaranteed departure
From:
US $2,900 per person
Multiple Room Types

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What our customers ask about this tour

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Try a different search term or ask a question to this adventure's experts

S
Steve
Asked on July 7th, 2025
My niece and I are looking for assistance in hotels, hot air balloons ride, Food making class, winery tours in Tuscany. The Cianti Festival is happening during this time frame and we would like to go to that. We want to spend time in San Gamignano, Sienna, Pazano and maybe further east.
Tour Details
Travel Support
- Explore!Operator•Written July 2025
  We do not offer any custom tour packages nor do we offer assistance in booking just hotels and day tours. We do offer our packages as is.
L
Luis
Asked on May 29th, 2025
Could you please advise the demographics for this trip? I'm 37 so not wanting to be with too many older folk or couples.
Age Range
Tour Details
- Explore!Operator•Written May 2025
  Generally our demographic leans more towards the 50+ range for a tour like this one but in saying that we have been getting a lot more mixed age groups of late!
A
Andy
Asked on July 3rd, 2022
What 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
Accommodation
Price / Availability
Single supplement
- Explore!Operator•Written July 2022
  The single supplement would be from £270.00 per person.
L
Liam
Asked on March 15th, 2022
What is the 1,460.00 for?
Price / Availability
Tour Details
- Explore!Operator•Written March 2022
  The 1,460.00 would be the cost of the trip.
J
Joel
Asked on February 26th, 2022
Do 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
Group size
Tour Details
Transport
- 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, 2022
Are single rooms available?
Accommodation
Single supplement
- 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.

From

$2,870

-9%

US $2,600 per person

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

Select Date

1 Adult2 Adults, 1 Child2 Children

Best price guarantee Learn More

Plan your adventure:

Good to Know

Tour ID: 124710

Currency
€
Euro
Italy
Plugs & Adapters
As a traveler from USA, Canada, England, Australia, New Zealand, South Africa you will need an adaptor for type L.
Type L
Italy
Visa
- Unfortunately we cannot offer you a visa application service. Whether you need a visa or not depends on your nationality and where you wish to travel. Assuming your home country does not have a visa agreement with the country you're planning to visit, you will need to apply for a visa in advance of your scheduled departure.
- Here is an indication for which countries you might need a visa. Please contact the local embassy for help applying for visas to these places.
Payment information
- For any tour departing before July 16th, 2026 a full payment is necessary. For tours departing after July 16th, 2026, a minimum payment of 10% is required to confirm your booking with Explore!. The final payment will be automatically charged to your credit card on the designated due date. The final payment of the remaining balance is required at least 75 days prior to the departure date of your tour. TourRadar never charges you a booking fee and will charge you in the stated currency.
- Some departure dates and prices may vary and Explore! will contact you with any discrepancies before your booking is confirmed.
- The following cards are accepted for "Explore!" tours: Visa, Maestro, Mastercard, American Express or PayPal. TourRadar does NOT charge you an extra fee for using any of these payment methods.
Cancellation Policy
- Your money is safe with TourRadar, as we only pay the tour operator after your tour has departed.
- TourRadar is an authorized Agent of Explore!. Please familiarize yourself with the Explore! payment, cancellation and refund conditions.
Accessibility
Some tours are not suitable for mobility-restricted traveler, however, some operators may be able to accommodate special requests. For any enquiries, you can contact our customer support team, who are ready and waiting to help you.
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Pisa

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San Gimignano - Castellina in Chianti

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Castellina in Chianti

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Pienza

Included Activities

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Pienza

Included Activities

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San Quirico d'Orcia to Montalcino

Included Activities

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Montalcino to Florence

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