Does it mean tour will provide car let us driving? If yes, one car per person ? Or you will group us , then one car per group?

For all the times when the group has to drive to a location, you will be transported as a group as a whole on a midi bus. You will not have to do any driving yourself on the tour.

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

US $2,900 per person

Tuscany Walking and Wine

8 days

•

From Pisa to Florence

4.5 (25 reviews)

View all
Best lasagne in Pienza (side street). All wine experiences great but especially enjoyed Montichiello & their cellars.
Gill•traveled in May4.7
View all

From

US $2,900 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 departure month

1 Adult2 Adults, 1 Child2 Children

Pay only 10% today. The rest is due 75 days before departure. Learn more

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Plan your adventure:

Platinum Operator: Explore!
Hiking & Trekking: Conquer epic trails and breathtaking landscapes
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+

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Image of a map showing the route of the tour

Itinerary

Intro
Introduction
Day 1
Pisa
Pisa
Start point
Piazzale D'ascanio, 1, 56121 Pisa PI, Italy (Pisa Airport, Arrivals Hall, 18:30)
Accommodation
Hotel 3* (Hotel Bologna)
Optional Activities
- Climb the Leaning Tower of Pisa
- Explore Pisa in more depth
Landmarks
Leaning Tower of Pisa
Campo del Miracoli
Pisa Central Station
Day 2
San Gimignano - Castellina in Chianti
San Gimignano - Castellina in Chianti
Meals
Lunch
Accommodation
Hotel 3* (Hotel Colle Etrusco Salivolpi)
Included Activities
- Hike along the Via Francigena pilgrimage route to San Gimignano
- Wine tasting at Sovestro winery
Optional Activities
- Visit Torre Grossa
- Visit the Duomo in San Gimignano
Landmarks
San Gimignano
Torre Grossa
Duomo of San Gimignano
Sovestro Winery
Castellina in Chianti
Day 3
Castellina in Chianti
Castellina in Chianti
Meals
Breakfast, Lunch (Light lunch of local cheeses and cold cuts at Castello La Leccia winery)
Accommodation
Hotel 3* (Hotel Colle Etrusco Salivolpi)
Included Activities
- Hike through countryside on strade bianchi routes
- Wine tasting and lunch at Castello La Leccia winery
Optional Activities
- Explore the village of Castellina
- Swim in the hotel pool
Landmarks
Castello La Leccia Winery
Day 4
Castellina in Chianti - Siena - Pienza
Castellina in Chianti - Siena - Pienza
Accommodation
Hotel 3* (Relais II Chiostro di Pienza Hotel)
Included Activities
- Orientation visit to Siena with free exploration
Optional Activities
- Visit the Piazza del Campo
- Visit the Torre del Mangia
- Visit the Duomo in Siena
Landmarks
Piazza del Campo
Torre del Mangia
Duomo of Siena
Pienza
Day 5
Pienza
Pienza
Meals
Breakfast
Accommodation
Hotel 3* (Relais II Chiostro di Pienza Hotel)
Included Activities
- Panoramic loop hike around Pienza (the 'Gladiator hike')
Optional Activities
- Cheese tasting at Armellini family cheese shop in Pienza
Landmarks
Vitaleta Chapel
Day 6
Montalcino - Val d'Orcia - San Quirico d'Orcia - Pienza
Montalcino - Val d'Orcia - San Quirico d'Orcia - Pienza
Meals
Breakfast, Lunch (Picnic lunch along the trail)
Accommodation
Hotel 3* (Relais II Chiostro di Pienza Hotel)
Included Activities
- Wine tasting of Brunello di Montalcino wine in Montalcino
- Hike through Val d'Orcia to San Quirico d'Orcia with picnic lunch
Landmarks
Montalcino
Val d'Orcia
San Quirico d'Orcia
Day 7
Pienza - Florence
Pienza - Florence
Meals
Breakfast
Accommodation
Hotel 3* (Hotel San Giorgio)
Included Activities
- Orientation walk of Florence with tour leader
Optional Activities
- Visit the Ponte Vecchio
- Visit the Cathedral of Santa Maria del Fiore
- Walk to Piazzale Michelangelo for city views
Landmarks
Ponte Vecchio
Cathedral of Santa Maria del Fiore
Piazzale Michelangelo
Florence Centrale Railway Station
Day 8
Florence
Florence
End point
Viale Machiavelli 25 50125 Firenze, Italy (Classic Hotel Florence, Hotel reception, 09:00)
Meals
Breakfast
Landmarks
Florence Centrale Railway Station
Pisa Galileo Galilei International Airport
Florence Peretola Airport

Landmarks
Leaning Tower of Pisa
Campo del Miracoli
Pisa Central Station

Landmarks
San Gimignano
Torre Grossa
Duomo of San Gimignano
Sovestro Winery
Castellina in Chianti

Landmarks
Castello La Leccia Winery

Landmarks
Piazza del Campo
Torre del Mangia
Duomo of Siena
Pienza

Landmarks
Vitaleta Chapel

Landmarks
Montalcino
Val d'Orcia
San Quirico d'Orcia

Landmarks
Ponte Vecchio
Cathedral of Santa Maria del Fiore
Piazzale Michelangelo
Florence Centrale Railway Station

Landmarks
Florence Centrale Railway Station
Pisa Galileo Galilei International Airport
Florence Peretola Airport

Accommodation
Guide
Meals
Additional Services
Transport
Optional Extras

What's Not Included

Flights
Insurance
Additional Services

Where You'll Stay

Hotel Bologna
Hotel 3*
day 1
Hotel Colle Etrusco Salivolpi
Hotel 3*
Days 2, 3
Relais II Chiostro di Pienza Hotel
Hotel 3*
Days 4, 5, 6
Hotel San Giorgio
Hotel 3*
day 7

All accommodations are subject to change

Operated by

Explore!

Platinum Operator

Rating: 4.5 (11,880 reviews)
Response time: within 1 day
Response rate: 68%
Cancellation policy: Learn more

Traveler Reviews

4.5

Overall rating based on 25 Reviews

Itinerary
4.6
Transport
4.8
Guide
4.9
Accommodation
4.1
Food
4.2
Tour Operator
4.5

Michelle4.5•September 2025
The walks, the wine tasting experience at Rocce dell Macie in Chianti region. Change from itinerary a great choice.
Traveled in September 2025
Review collected by Explore!
Margaret4.5•January 2025
Great group, lovely guide and a fabulous location. Wine tasting a highlight and viewpoints visited.
Traveled in September 2025
Review collected by Explore!
Silvana4.0•October 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
Cynthia3.0•October 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
Philip4.0•October 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
John4.7•April 2023
Knowledgeable local guide who was extremely helpful and passionate about his home country
Traveled in April 2023
Review collected by Explore!
Eva4.7•April 2023
Outstanding natural beauty of the region. Pienza, lovely little town
Traveled in April 2023
Review collected by Explore!
Elizabeth4.8•April 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!
Kim4.5•May 2023
So many. Every day provided new highlights
Traveled in April 2023
Review collected by Explore!
David4.8•May 2023
Walking beautiful countryside. Guide very well informed.
Traveled in April 2023
Review collected by Explore!

Dates & Prices

Select departure month

1 Adult2 Adults, 1 Child2 Children

Upcoming departures

Hurry, deals only available for a limited time!

Ends on 11 Nov, 2026

Instant Confirmation
From Sunday
9 May, 2027
To Sunday
16 May, 2027
English
This departure date is available and will 100% depart
Guaranteed departure
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US$3,140 per person
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Price based on Shared Room
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From Sunday
23 May, 2027
To Sunday
30 May, 2027
English
This departure date is available and will 100% depart
Guaranteed departure
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US$2,900 per person
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Price based on Shared Room
Instant Confirmation
From Sunday
6 Jun, 2027
To Sunday
13 Jun, 2027
English
This departure date is available and will 100% depart
Guaranteed departure
From:
US$3,140 per person
Sign up to unlock savings
Price based on Shared Room
Instant Confirmation
From Sunday
5 Sep, 2027
To Sunday
12 Sep, 2027
English
This departure date is available and will 100% depart
Guaranteed departure
From:
US$3,140 per person
Sign up to unlock savings
Price based on Shared Room
Instant Confirmation
From Sunday
12 Sep, 2027
To Sunday
19 Sep, 2027
English
This departure date is available and will 100% depart
Guaranteed departure
From:
US$3,140 per person
Sign up to unlock savings
Price based on Shared Room
Instant Confirmation
From Sunday
19 Sep, 2027
To Sunday
26 Sep, 2027
English
This departure date is available and will 100% depart
Guaranteed departure
From:
US$3,140 per person
Sign up to unlock savings
Price based on Shared Room
Instant Confirmation
From Sunday
3 Oct, 2027
To Sunday
10 Oct, 2027
English
This departure date is available and will 100% depart
Guaranteed departure
From:
US$3,140 per person
Sign up to unlock savings
Price based on Shared Room

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What our customers ask about this tour

The content in our FAQ section is subject to change.

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C
Chris
Asked on July 18th, 2026
Does it mean tour will provide car let us driving? If yes, one car per person ? Or you will group us , then one car per group?
Transport
- Explore!Operator•Written July 2026
  For all the times when the group has to drive to a location, you will be transported as a group as a whole on a midi bus. You will not have to do any driving yourself on the tour.
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.

Good to know

Tour ID: 124710

The practical details for your trip across Italy: money, plugs and flexible ways to pay, all in one place.

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Pay in installments
Spread the cost in interest-free biweekly installments of $157.
Deposit only
Book now with just a 10% deposit. The remaining balance is due 75 days before departure.
€ - Euro
You’ll encounter Euro in Italy.
Plug type L
You’ll need an adapter for these sockets in Italy.

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
  Used in Italy
Visa
Whether you need a visa depends on your nationality and how long you stay. We can’t process visas for you, but here’s a quick indication for this trip.
This is only an indication. Visa rules depend on your passport, trip length and purpose. Always confirm with the official embassy or consulate before you travel.
Payment information
Pay now
A 10% deposit
Balance due
75 days before departure
Installments
Interest-free, every two weeks
Currency
USD
Booking fee
None
Book now with just a 10% deposit and pay the rest later. The remaining balance is due 75 days before departure, charged automatically to your card, or you can split it into interest-free biweekly installments of $157 at checkout. Everything is charged in USD, and TourRadar never adds a booking fee. Any trip departing before January 18th, 2027 will need to be paid in full at checkout.
Accepted for Explore! tours
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Cancellation Policy
Cancellation terms may vary per tour. Please check for the full cancellation policy here.
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Our travel protection from our award-winning partner, XCover, means you and your travel companions can book with peace of mind knowing there’s protection available in case your trip doesn’t go to plan. At checkout you will be able to select between different options in case you or the tour are eligible for insurance. In case no option is available, you are always able to purchase travel insurance outside of TourRadar.
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From

US $2,900 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 departure month

1 Adult2 Adults, 1 Child2 Children

Pay only 10% today. The rest is due 75 days before departure. Learn more

Best price guarantee Learn More

Plan your adventure:

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Where You'll Stay

Traveler Reviews

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What our customers ask about this tour

Pay in installments

Deposit only

€ - Euro

Plug type L

Currency

Plugs & adapters

Visa

Payment information

Accepted for Explore! tours

Cancellation Policy

Insurance

Best price guarantee

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