Chianti Walking & Wine
Chianti Walking & Wine
Chianti Walking & Wine
8 Days Starting and ending in Castellina
Visiting: Pisa, Castellina in Chianti, Greve in Chianti, Radda in Chianti, Province of Siena, Chianti, Metropolitan City of Florence, San Gimignano
Tour operator:
Tour code:
TDC
Guide Type:
Fully Guided
Group size:
5 - 16
Physical rating:
Leisurely / Moderate
Age range:
18-99
Special diets catered:
Please inform Exodus of specific dietary requirements
Tour operated in:
EnglishTrip Styles:
Interests:
Activities:
From:
$2617
$2245 (USD)
Operator discount: -$372
-14%
Tour Overview
With its Renaissance cities, mediaeval villages and cypress-lined avenues snaking through vineyards, southern Tuscany is the perfect place for a relaxing guided walking holiday. Based at the tranquil Villa Casalta, on our tour we visit beautiful San Gimignano, the market town of Greve in Chianti, the UNESCO World Heritage Site of Siena and the magnificent city of Florence. During the week we sample several varieties of the world-renowned local Chianti and have the opportunity to learn more about Italian wine at the Wine School of Siena.
Highlights
Itinerary
Day 1 : Start Castellina In Chianti.
Location: Pisa, Castellina in Chianti
Accommodation: Villa Casalta
Meals Included: Dinner
Start at Villa Casalta, our beautiful villa 2km from Castellina in Chianti.
In the evening our guide will hold a welcome meeting to discuss the week
ahead, give advice on the local area and answer any questions.
Day 2 : Visit Mediaeval Market Town Of Greve In Chianti And The Hilltop Village Of Montefioralle; Afternoon Wine Tasting In Castellina.
Location: Greve in Chianti
Accommodation: Villa Casalta
Meals Included: Breakfast, Dinner
Today we head to the mediaeval market town of Greve in Chianti walking
through a magnificent setting of olive groves and vineyards. On the way, we
will stop in the fortified hilltop village of Montefioralle, considered the
most ancient 'borgo' in Chianti. After lunch we enjoy a wine tasting in
a local winery before heading back to our farmhouse for dinner.
Day 3 : Walk To Radda In Chianti, The Heart Of The Chianti Area
Location: Radda in Chianti
Accommodation: Villa Casalta
Meals Included: Breakfast
This morning we will set out for a local history walk to the heart of the
Chianti area, covering the route from Villa Casalta to Radda in Chianti. We
will take a walk through local woodlands where we can admire the so famous
emerald vineyards valleys. In the afternoon we will have the chance to taste
the much acclaimed Chianti Classico wine at a local winery.
Day 4 : Travel To Siena And Explore The Stunning Historic Centre; Learn About Tuscan And Italian Wines At The Wine School.
Location: Province of Siena
Accommodation: Hotel
Meals Included: Breakfast, Dinner, Villa Casalta
After breakfast we make our way to the centre of Siena for a day exploring
this fascinating city. We have time to visit the numerous museums and
stunning Duomo and to relax in one of the many outdoor cafés in Piazza del
Campo, home of the world famous Palio horse race. Please note that shoulders
should be covered for entering the Duomo. You may also like to visit the many
boutiques specializing in local products and cutting edge Italian fashion. In
the afternoon we also have the opportunity to learn about Tuscan wines on a
1-hour fun interactive course at the Tuscan Wine School.
Day 5 : Free Day To Visit Other Chianti Villages Or Relax By The Pool.
Location: Chianti
Accommodation: Villa Casalta
Meals Included: Breakfast
Today is free to rest any tired legs at the poolside. Alternatively, your
leader can advise on local Chianti wine tasting tours and cooking classes or
offer assistance for unguided walks or daytrips.
Day 6 : Discover The Magnificent City Of Florence, Considered The Birthplace Of The Renaissance.
Location: Metropolitan City of Florence
Accommodation: Villa Casalta
Meals Included: Breakfast, Dinner
Our destination today is the magnificent city of Florence, the birthplace of
the Italian Renaissance with an enormous wealth of historical sites, museums,
galleries, churches and architectural delights. Most of the great artists,
thinkers and builders from Renaissance history passed through or lived in
Florence when it was under the rule of the Medici family, the most famous
patrons of the 16th century. But Florence is not just a Renaissance
showpiece: once you have had your fill of the historical trail there are many
other things to see and do. The city has not ceased to be a centre of
learning, and there is a university, many art and language schools and a
large student population to liven up the café-bars, restaurants and
nightclubs. There are also some great markets and chic boutiques. From April
to July, Florence also holds one of Europe's major cultural events, a
festival of opera and classical music called the Maggio Musicale Fiorentino.
There are no guided tours organised for the day but there's an option to join
one of the free walking tours in the morning. This will then leave you enough
time to visit the Uffizi galleries. If you wish to do so we recommend that
you prebook your ticket online to avoid lengthy queues. An ideal slot time
would be around 2 pm. it can be earlier if you're not interested in joining
the morning free walking tour. Tickets can be purchased throughÂ
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Day 7 : Walk To Picturesque San Gimignano With Free Time To Explore Palazzo Comunale, Pinacoteca And Torre Grossa.
Location: San Gimignano
Accommodation: Villa Casalta
Meals Included: Breakfast, Dinner
After a  transfer to the quaint hamlet of San Donato, we walk through the
farm grounds following the pathway to Montauto and on up to the picturesque
mediaeval town of San Gimignano. The walk is not long and should take
approximately 3 hours. The afternoon is spent exploring this beautiful town
including visits to the Palazzo Comunale, Pinacoteca and Torre Grossa and
there is some free time to wander and soak up the atmosphere.Â
Day 8 : End Castellina In Chianti.
Location: Castellina in Chianti, Pisa
Meals Included: Breakfast
Trip ends at Villa Casalta.
What's Included
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Flights from London (if booking incl. flights)
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All transport and listed activities
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All breakfasts, 5 dinners, 3 wine tastings
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All accommodationÂ
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Tour leader throughout
What's Not Included
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/Local taxes (approx. EUR 14 per person, see Trip Notes)/
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Single accommodation (available on request)
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Travel insurance
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Visas or vaccinations
Accommodation
Surrounded by Tuscan hills, Hotel Le Renaie occupies a privileged spot in the little village of Pancole, just 4mi (6.5km) from San Gimignano. Here, the Sabatini family has created an intimate, friendly retreat with just 25 air-conditioned rooms and plenty of places to mingle.
Under the beautiful Italian summer sun, the swimming pool area (which has a separate hot tub) is the perfect place to cool down; alternatively, find a shady spot in the flower-filled gardens to sit, chat or read a book. Come evening, gather in the bar-restaurant for delicious Tuscan cuisine and a glass or two of excellent local wine. It’s a popular stop for Pancole residents, so you know it’s good. There are also games tables (table football, billiards and ping pong) to keep the entertainment going or you can take your drinks onto the bar terrace for views over the garden, which is filled with hydrangeas and citrus plants.
Amenities
Swimming pool (usually open May to mid-October)
Restaurant serving traditional Tuscan meals
Bar/cafeteria for light snacks and lunches (open every day)
Games tables
Worth knowing
A limited number of rooms have a balcony (facing the pool or garden) and these are assigned by the hotel
Pool opening dates are subject to local weather conditions and pool maintenance requirements; cooler months may not be suitable for swimming
Food
All breakfasts, 5 dinners and 3 wine tastings are included.
Breakfast is usually a continental-style buffet. The five included dinners
are taken at Villa Casalta (drinks not included). Vegetarian choices are
available - please advise us of dietary requirements on booking.
Check out our Q&As
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Are children permitted to take part in the tour?
Minimum 18 years old people can go on this tour.
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Are flights included in this tour?
International flights are not included with this tour.
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Who is Exodus Travels?
At Exodus Travels, we've been exploring the world for nearly 50 years. From Walking and Trekking, Cultural and Cycling, Responsible Wildlife, to Polar and our new Premium Adventures, we are proud to offer award-winning small group and self-guided tours to 100+ countries worldwide.
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Is there a supplement for solo travellers?
If you would like to be paired with a tour member of the same gender, there is no additional charge. A single supplement can be requested if you would like your own room.
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What is the maximum group size?
16
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Do you require a visa for this holiday?
No visa required for British passport holders. Please note in Italy it is compulsory to carry ID with you at all times.
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Can you assist with pre or post tour accommodation?
We are happy to assist with pre and post tour accommodation. Please enquire for detailed information.
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Are the local guides on the tour English speaking?
Yes.
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Are vaccinations required for this tour?
There are no specific health risks.
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What happens if I need to change my holiday date once I’ve booked?
If you wish to make any changes to your booking, particularly if you need to alter any flights booked through us, please let us know as soon as possible. There is a booking or flight amendment fee of £40 per change and flight amendments often incur extra airline costs depending on the changes to be made and if the ticket has been issued or not.
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How long has the tour company been trading?
Exodus has been trading since 1974
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What documents will I receive before I travel?
Your final joining instructions and flight details, if booked with us, will then be sent out 2 to 3 weeks before departure. If you would like a hard copy posted, or if you require these any earlier, please contact the customer operations team. We advise that if you are booking connecting travel before receiving these, please ensure you leave plenty of time.
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Do you operate a “single share” option and how does it work?
Travellers are welcome to opt to share a room with a tour member of the same gender for no additional charge. If you'd like your own room, we can request a single supplement so that you will have your own room throughout.
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Can I join the tour once it has departed?
You are welcome to meet the group after the tour has departed however there is no reduction in rate for joining a tour after the departure date.
Reviews from Travellers on this Tour
Dates & Availability
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Oct 18, 2025 - Oct 25, 2025Book with Confidence
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Transfer as credit to Future Tours
Exodus allows you to transfer existing payments to a future tour to avoid cancellation fees if you can't travel and inform exodus, 43 days before departure.
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Low Deposit
Exodus requires a minimum deposit of 25% or the full booking value, whichever is less, with the final balance not due until 90 days before departure.
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Cancellation Policy
We don't charge a cancellation fee, here is a summary of exodus charges.
Up to 70 days before tour starts: Forfeit 100% of deposit.