Chianti Walking & Wine

Chianti Walking & Wine

8 Days From



Chianti Walking & Wine

8 Days Starting and ending in Castellina

Visiting: Italy

Tour operator:

Exodus Adventure Travels

Tour code:


Guide Type:

Fully Guided

Group size:

5 - 16

Physical rating:

Leisurely / Moderate

Age range:


Special diets catered:

Please inform Exodus of specific dietary requirements

Tour operated in:



Sightseeing, Walking

From: $2617 $2183 Operator discount: -$372 Mid-Year Mayhem Discount: -$62 -17%

NB: Prices correct on 18-Jun-2024 but subject to change.

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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.


  • Stay in a converted farmhouse

  • Enjoy the fabulous Chianti wines

  • Walk the classic rolling hills of Tuscany


Day 1

Fly to Pisa; transfer to Villa Casalta, 2kms from Castellina in Chianti
(transfer approx. 1hr30mins).

Day 2

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

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

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

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

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 through


Day 7

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. 

Day 8

Transfer to Pisa; fly to London.

Please note that at times, especially during summer months, the inbound
flight can be late in the evening. In this instance you will have additional
time to spend in Pisa. Leader will take care of all arrangements in terms of
transport from/to the airport and the city centre and luggage storage. It may
also happen that, for logistical reasons, on return we will have to be at the
airport earlier than normally scheduled. This will mean a longer waiting time
before checking in. 

What's Included

  • Flights from London (if booking incl. flights)

  • All transport and listed activities

  • All breakfasts, 5 dinners, 3 wine tastings

  • All accommodation 

  • Tour leader throughout

What's Not Included

  • /Local taxes (approx. EUR 14 per person, see Trip Notes)/

  • Single accommodation (available on request)

  • Travel insurance

  • Visas or vaccinations


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.


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


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

  • Are children permitted to take part in the tour?

    Minimum 18 years old people can go on this tour.

  • 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.

  • 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.

  • Are the local guides on the tour English speaking?


  • Are vaccinations required for this tour?

    There are no specific health risks.

  • Are flights included in this tour?

    International flights are not included with this tour.

  • 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.

  • 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.

  • What is the maximum group size?


  • 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.

  • How long has the tour company been trading?

    Exodus has been trading since 1974

  • 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.

  • 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.

  • 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

Chianti walking and wine

The setting in the converted farmhouse is absolute

The setting in the converted farmhouse is absolutely idyllic - but remember that September is the beginning of autumn and the altitude is high, so you really need to pack something warm for the evenings. The staff are really friendly and very helpful and the accommodation is clean. I did find the twin beds narrow and the shower a little cramped : but then you get used to it. The meals at Castella were excellent, especially the antipastas, and the buffet on the first night was to die for - but overall I was disappointed at the vast amount of meat and the lack of fresh salads/vegetables. We found the same trend even when eating out ..... meat, meat , meat. Perhaps the wine compensated for it? I'm sure I got my 5 -a-day from the wine alone!! it flowed! Oh, and don't forget the gelatos! I must say we had a fantastic guide- nothing was too much for him. We'd slog away at the "undulations" (the in-word on our tour)and spent 2-3 hours relaxing in the town, while he'd WALK back again to pick up the minibus. And the wine-tastings were brilliant: we've all learnt about chianti classico. Fantastic cheeses and delicious olive oils were provided. No tasting was the same! Honestly, we all got on so well. Thanks Mark for making our tour so enjoyable and such fun.

Right First Time!

This was our first actual trip with Exodus and it

This was our first actual trip with Exodus and it was all that we hoped for, and more. The balance of walking, wine tasting and culture was spot on! Villa Casalta accommodation was great - simple in a traditional way, owner and Marguerite warmly welcoming and helpful, beautiful swimming pool (used by several of us even though it was end of Sept), entertaining dog (Stella) and cat, with only a slow off-road 20 minute walk to pretty town of Castellina.


From sign up to last day this trip was fabulous. O

From sign up to last day this trip was fabulous. Our guide worked tirelessly to insure that our group of 16 was always taken care of on the hike and at the villa. Liz Procter was a completely professional guide who made everyone feel comfortable!! The scenery in Tuscany was gorgeous, and Villa Casalta was a treat to have as a base for the entire week! Hope to use Exodus Travel again and soon!

Chianti walking and wine

Another excellent Exodus trip. Some good walking t

Another excellent Exodus trip. Some good walking through Tuscany combined with other activities such as a guided tour of Siena, visit to Florence, visited to wineries and much more. Accommodation in Villa Casalta was good on the above scale.

Tuscany Walking and Wine

A really enjoyable and varied week in Tuscany. Th

A really enjoyable and varied week in Tuscany. Three lovely walks through forests and vineyards. Stunning hilltop villages and market towns. Excellent wine tastings and winery visits, each a little different, and we certainly drank a lot of local Chianti. Liz, our guide, was efficient, knowledgeable, capable and so friendly. We had plenty of time to explore the cities of Siena and Florence at our own pace, and on our free day most of us opted for a cookery class at a local restaurant. Enormous fun and the lunch we helped produce, was amazing. The family run farmhouse where we stayed was full of character, and they made us so welcome. The evening meals were generous and based on local produce and served with their own estate wines.

Super relaxing walking and wine in Chianti with brilliant tour leader

Brilliant tour leader, lovely group of travellers,

Brilliant tour leader, lovely group of travellers, excellent hotel, and varied mix of activities.


The trip had a really good balance of activities,

The trip had a really good balance of activities, with plently to do while still leaving you time to relax and chill out. Tuscany is so beautiful and Fattoria Voltrona was a great place to stay. I would definitely recommend this trip to my friends.

Excellent well balanced trip

This trip is a good mix of walking, city culture,

This trip is a good mix of walking, city culture, great wine tasting and good food. The walks are leisurely - undulating - through lovely county side and vineyards. Not too long but long enough to know you have done something. Local guided tours had been arranged in Siena and Florence which made it more focused since there is really only time for a taster! - definitely go back for a longer trip to see all they both have to offer. The arranged wine tastings were very informative especially the one at the Tuscany wine school in Siena - we will be on the look out for the wines we tasted. The local restaurants used all served excellent food as did the Vila Casalta where we stayed. We also took part in an italian cooking lesson run by Edith on our free day. Well worth going to - but she only takes cash. Our guide Liz - was very experienced, very informative and knowledgeable. All in all an excellent holiday.

A very enjoyable holiday!

A very enjoyable week away. Comfortable rustic acc

A very enjoyable week away. Comfortable rustic accommodation with friendly staff set in the beautiful surrounding Chianti countryside. A relaxed balance of healthy moderate walking, interesting wine tasting and well planned city visits.

First trip with Exodus

We had a thoroughly enjoyable varied trip though t

We had a thoroughly enjoyable varied trip though the walking was more challenging than we anticipated. The uphill and down dale rocky walking was harder for us as we are both in our 70s and these days we have not done so much of this type of walking. Nevertheless, we had an excellent guide in Liz Proctor who made sure that we paced our walking and with her knowledge of the countryside and terrain through woodland, olive groves and vineyards combined with a good humoured small group of 6 persons made our walking very enjoyable. The wine tasting and classes were very informative and fun. On the city days in Sienna and Florence we had excellent guided walks and an in-depth insight into the culture and history ofthese 2 beautiful cities both of which we have visited twice before. The weather was more chilly than expected and the farmhouse although welcoming was not warm enough in the morning or when we came home each

Read all 62 reviews

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    Exodus Adventure Travels allows you to transfer existing payments to a future tour to avoid cancellation fees if you can't travel and inform exodus adventure travels, 43 days before departure.

  • Low Deposit

    Exodus Adventure Travels 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.

  • Cancellation Policy

    We don't charge a cancellation fee, here is a summary of exodus adventure travels charges.

    Up to 70 days before tour starts: Forfeit 100% of deposit.

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