Walkers in Montefioralle

Chianti Walking & Wine

8 days
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Traveller ratings
4.7 / 5 from 38 reviews >
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Way to Travel:
Guided Group
Walking & Trekking
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Discover picturesque towns and delicious wines in Tuscany

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.


  • Walk the classic rolling hills of Tuscany
  • Stay in a converted farmhouse
  • Enjoy the fabulous Chianti wines

Key information

  • 7 nights renovated farmhouse with panoramic swimming pool
  • 5 days gentle walking and sightseeing
  • Low altitude throughout
  • Centre-based holiday

What's included

  • All breakfasts, 5 dinners, 3 wine tastings
  • All accommodation 
  • All transport and listed activities
  • Tour leader throughout
  • Flights from London (if booking incl. flights)

What's not included

  • Travel insurance
  • Single accommodation (available on request)
  • Visas or vaccinations
Call for general departures:
(354) 567 8978
Call for tailormade trips:
+44 (0)20 8772 3874
Trip Notes

Click on the button below for detailed Trip Notes containing all the particulars about this trip, including kit lists and practical information.

Note: these can vary by departure; you can check out the specific Trip Notes for your chosen adventure on the dates & prices page.


Days of Walking & Trekking



Manmade paved tracks, tarmac, forest trails to grave

Day by day breakdown
Day 29.0km/5.0miles
Day 312.0km/7.0miles
Day 48.0km/4.0miles
Day 64.0km/3.0miles
Day 710.0km/6.0miles

Responsible Travel

At Exodus we believe in the power of Responsible Travel.

Every time we travel, we are part of a global movement that creates jobs, builds more sustainable societies, encourages cultural understanding and safeguards common natural and cultural heritage. To learn more about what Responsible Travel means to Exodus click here… 


  • Day 1

    Fly to Pisa; transfer to Castellina in Chianti

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

    Meals included: Dinner
  • Day 2

    Visit mediaeval market town of Greve in Chianti and the hilltop village of Montefioralle; afternoon wine tasting in Castellina

    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. We return to our farmhouse in time for a tasting of the local wine before dinner.

    Meals included: Breakfast Dinner
  • Day 3

    Walk to Radda in Chianti, the heart of the Chianti area

    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.

    Meals included: Breakfast
  • Day 4

    Travel to Siena and explore the stunning historic centre; learn about Tuscan and Italian wines at the Wine School

    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.

    Meals included: Breakfast Dinner
  • Day 5

    Free day to visit other Chianti villages or relax by the pool

    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.

    Meals included: Breakfast
  • Day 6

    Discover the magnificent city of Florence, considered the birthplace of the Renaissance

    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.

    If you would like to visit the Uffizi galleries we recommend that you prebook your ticket online to avoid lengthy queues. Tickets can be purchased through http://www.b-ticket.com/b-ticket/uffizi/venue.aspx. Please ensure that your allocated time slot is between 11.45 and 16.00.

    Meals included: Breakfast Dinner
  • Day 7

    Walk to picturesque San Gimignano with free time to explore Palazzo Comunale, Pinacoteca and Torre Grossa

    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. 

    Meals included: Breakfast Dinner
  • Day 8

    Transfer to Pisa; fly to London.

    Transfer to Pisa; fly to London.

    Meals included: Breakfast
Trip Notes

Click on the button below for detailed Trip Notes containing all the particulars about this trip, including kit lists and practical information.

Note: these can vary by departure; you can check out the specific Trip Notes for your chosen adventure on the dates & prices page.

Essential Info



No visa required for British passport holders.
Please note in Italy it is compulsory to carry ID with you at all times.



There are no specific health risks.

Eating and Drinking

All breakfasts 5 dinners and 3 wine tastings are included.

Breakfast is usually a continental style buffet. Of the 5 included dinners, three are taken at Villa Casalta and a reasonable amount of wine is included. Two are taken in local restaurants (drinks not included). Vegetarian choices are available - please advise us of dietary requirements on booking.


April and May departures can expect warm days and although rain is possible, it seldom lasts long. Nights may still be rather cool. We strongly recommend a fleece-lined jacket or warm sweater in these months. June sees the start of summer and July and August can become quite hot by mid afternoon, so this time is kept free for lunch. Although rain is unusual, torrential cloudbursts are not unknown. September and October are cooler and wetter, yet visibility is often better. Swimming is usually still possible at this time.

Is this trip for you?

This trip offers a good mix of city and countryside walks. During the days with walking included, the terrain and type of path will vary from manmade paved tracks, tarmac, forest trails to gravel. The walks are not technically difficult although some ascents and descents should be expected, so a reasonable amount of fitness is required. Please be aware that the Radda walk, on day 3 can be challenging due to the length and the hilliness of the walk.
The area is quite hilly and the majority of drives, although short, follow twisty mountain roads through wooden areas. Tuscany can also be very hot, possibly high 30s (degC) in the summer.

Call for general departures:
(354) 567 8978
Call for tailormade trips:
+44 (0)20 8772 3874
Trip Notes

Click on the button below for detailed Trip Notes containing all the particulars about this trip, including kit lists and practical information.

Note: these can vary by departure; you can check out the specific Trip Notes for your chosen adventure on the dates & prices page.


Villa Casalta

You will spend 7 nights at Villa Casalta, a renovated farmhouse with swimming pool and en suite facilities. The villa is family-run and known for the fine home-made food prepared with traditional ingredients and locally produced wines and olive oil. Free Wi-Fi available. 

Call for general departures:
(354) 567 8978
Call for tailormade trips:
+44 (0)20 8772 3874
Trip Notes

Click on the button below for detailed Trip Notes containing all the particulars about this trip, including kit lists and practical information.

Note: these can vary by departure; you can check out the specific Trip Notes for your chosen adventure on the dates & prices page.

Expert Blog Entries

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  • Reviewed June 2018
    Richard Moore

    Beautiful Tuscany

    This eight-day trip to Tuscany took place in the Chianti hills some 2,000 feet above sea level, just outside Castellina. Our base was Villa Casalta, a beautiful converted farmhouse which boasts extensive views in all directions and an unheated swimming pool that provided invigorating dips at the end of the day. There were three lovely walks during the week, ranging from five to seven miles in length, over a variety of terrain, all finishing at local mediaeval villages, such as Greve, Radda and San Gimignano, and there were day trips to Siena and Florence, which were enhanced by excellent local guides. On each of the first three days there were also fascinating wine-tasting sessions at different locations. On our final day we had three hours to explore Pisa before our flight home.

    What was the most inspirational moment of your trip?

    There were so many inspirational moments. Here are a few: 1. the panoramic views on our walks 2. the Duomo (especially the Piccolomini Library) and the Piazza del Campo in Siena 3. the views of Florence from San Miniato al Monte, plus Giotto's Campanile beside the Duomo in the centre of the city 4. the frescoes in the Collegiata church in San Gimignano

    What did you think of your group leader?

    Our group leader, Liz Proctor, was exceptional in every way. Her briefings before each day's outing contained all the information we needed, and her advice was always very sound. She seemed to have an encyclopaedic knowledge of all the Tuscan roads, tracks and paths we travelled on, as well as restaurants and other places of interest when we arrived at our destination. She was an excellent driver, and we always felt in safe hands. She was very patient with those who walked more slowly than others and concerned for everybody's welfare. Her fitness was such that she was able to retrace her steps with apparent ease at the end of a walk in order to retrieve the minibus (while the rest of us were having lunch and looking round the place we'd arrived at!).

    Do you have any advice for potential travellers?

    Our weather was pretty mixed, so an anorak was an essential piece of clothing, and there were moments on some of the muddier, rockier paths of our walks when we would have been happier wearing walking boots than simply trainers.

    Is there anything else you would like to add?

    The food at Villa Casalta was generally good, but we did feel there was a lack of fresh fruit and vegetables on the occasions when we had supper there.
  • Reviewed May 2018
    Michael Littleton

    Great Experience

    This was a wonderful trip through the countryside of Tuscany. The Villa Casalta owner and her staff member was friendly and caring.

    What was the most inspirational moment of your trip?

    I really enjoyed the hiking. The countryside was beautiful! It reminds me of the foothills of the Appalachian Mountains in NC.

    What did you think of your group leader?

    Liz Proctor was a great group leader. She is a very good organizer and "den mother" for the members of the group.

    Do you have any advice for potential travellers?

    We boarded the wrong train going to Pisa before the start of the tour. It was on the same track and approximate departure time for our train. We had tickets for a regional train and it was a express train. The conductor charged us the cost of the ticket and 50 euros penalty for each person. It appears to be a money generator from the unwary!
  • Reviewed May 2018
    James Kearney


    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!

    What was the most inspirational moment of your trip?

    Just viewing the wonderful Tuscan hill and valleys.

    What did you think of your group leader?

    Incomparable! Liz was the BEST!!

    Do you have any advice for potential travellers?

    Come and enjoy!!
  • Reviewed October 2017
    Alex Henderson

    Best decision ever

    Exodus tours were recommended to me, and as someone who knows little about wine but loves to drink it I was keen on this trip. I also fancied some exercise and activities thrown in. I was slightly dubious about going alone but soon realised when I got there that exodus caters for people like me. I would say the trip is scaled correctly in terms of activity level, I particularly enjoyed the panzano and San gimignano walks. There's also loads to do on your free day, I rented a vintage fiat from castellina, some of the group went riding and others cooking so plenty of options. Couldn't recommend this trip enough.

    What was the most inspirational moment of your trip?

    All wine tastings are inspirational.

    What did you think of your group leader?

    He was amazing. There was (which I'm told is quite common on Exodus tours) a very diverse group of people of different ages and interests. Mark made sure everyone was looked after and entertained, he was also great at pointing out particular spots of interest (museums, gelato shops, enotecas, city tours) that made sure everyone got the most out of the time we had. He was also great with the walks, found the group pace early on so no one felt left behind.

    Do you have any advice for potential travellers?

    If you're going in mid sept as I did, dress like an onion. It's boiling in the direct sun and goes down about 10 in the shade and in the evenings sometimes. Still pleasant though, light jumpers are your best friends.
  • Reviewed September 2017
    Diane Leaver

    Chilled week in beautiful Tuscany

    Just returned from a really enjoyable trip. Stunning scenery, picturesque hillside towns, delicious food and wine and a great group of travelling companions. Mark our group leader was a lovely guy, whose 'can do' approach, knowledge and personality added to the overall enjoyment.

    What was the most inspirational moment of your trip?

    The vista over Florence from the arrival point was stunning.

    What did you think of your group leader?

    Mark was a really efficient and knowledgeable leader with a great personality. I felt that he'd handle difficult situations well, although thankfully there weren't any!

    Do you have any advice for potential travellers?

    The accommodation is in the hills and it can be a bit chilly up there in the mornings and evenings. Although the pace of the trip was chilled, we still packed a lot in, so you will probably welcome the free day.

    Is there anything else you would like to add?

    Mark fitted in an extra wine tasting for us which was welcomed by the group. Perhaps this could be added as part of the itinerary.
  • Reviewed September 2017
    Maggie Burghuber

    Chianti walking and wine

    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.

    What was the most inspirational moment of your trip?

    The scenery was so beautiful. Vineyards and olive groves lining the hillsides. Tall, slender Cyprus trees pointing their way up to the sky - hilltop villages, many of them walled. While walking the vistas would open up, one after the other and I never grew tired of taking them all in

    What did you think of your group leader?

    Mark was fantastic. He had so much energy : was up early, kept the timings so that the full itinerary was completed and more; his sense of humour was encouraging. We all know the Italian for "undulating" now - some of them were "cheeky undulations" - or a "little bit of an undulation". What I really found good was the way Mark would drop back and walk with the slower people to encourage them on. After we had walked 9 or 12 km he'd leave us at a town, so we could get a bite to eat, while he'd walk back to fetch the minibus up. Or he's run on ahead to bring the bus down to a meeting point. Incredible- he must be so fit. And whilst out on the walks he carried extra supplies of snacks for the group, so we could up the sugar intake and find our energy for the next etappe. I couldn't believe the extra mile he went to deliver pizzas on his day off. We were sitting in the town and saw him bent on a mission - staggering out with a pile of pizzas for those who chose not to leave the villa His planning was meticulous and he was so knowledgeable about the area. I would say he helped to make the tour so enjoyable

    Do you have any advice for potential travellers?

    Pack rainwear - Pack a torch Take something warm to wear in the evenings

    Is there anything else you would like to add?

    Just thank you to all who contributed to making this tour happen
  • Reviewed July 2017
    Julian Gale

    Julian Gale

    Great combination of walking, sightseeing and sampling the local food and wine.

    What was the most inspirational moment of your trip?

    Walking through the Tuscan countryside, and in particular the walk to San Gimignano, which ensured some beautiful views. The days in Siena and Florence.

    What did you think of your group leader?

    Liz was an excellent leader. Definitely one who goes above and beyond the call of duty. Very hard working and keen to make sure everyone has an enjoyable holiday. Good at communicating the options and making any necessary arrangements (such as restaurant bookings etc). She even fitted in a quick photo stop at the leaning tower of Piza on our way back to the airport.

    Do you have any advice for potential travellers?

    Worth making sure you also pack a long pair of walking trousers as one of the walks is through long grass areas where ticks might be lurking!

    Is there anything else you would like to add?

    As per my summary points, this is a particularly good option if you are looking for a mix of walking and sightseeing. Plus, if you like Italian food and wine then you are on to a sure fire winner!
  • Reviewed June 2017
    Colin Read

    Chianti walking and wine

    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.

    What was the most inspirational moment of your trip?

    Difficult to pick out one, but probably the excellent locally guided visit to Siena.

    What did you think of your group leader?

    Liz was everything one might wish from a really good group leader: friendly, helpful and knowledgeable. She was also an excellent driver of our Exodus minibus; felt much safer that on some previous trips with Italian drivers.

    Do you have any advice for potential travellers?

    Try to avoid flying with British Airways; we only narrowly escaped the 27th May IT debacle and were grateful to return the Gatwick only 4 hours late. BA short-haul is just another budget airline and not a particularly good one at that.
  • Reviewed May 2017
    Gail Oleszkowicz

    Chianti Walking and Wine

    A great mix of walking, wine tasting and touring Tuscany towns. Scenery just as advertised.

    What was the most inspirational moment of your trip?

    I liked San Gimignano the best of all the towns we visited.

    What did you think of your group leader?

    Liz Proctor was an exceptional leader: she really went out of her way to do everything possible to help everyone who needed it. Safety was a top priority and she was genuinely concerned for everyone's wellbeing.

    Do you have any advice for potential travellers?

    I am not used to walking on rough paths and was unable to train properly ahead of time. I managed but struggled. If you have health issues, do the training beforehand as suggested on the website to get in proper shape.

    Is there anything else you would like to add?

    The farmhouse, hostess, staff and food were exceptional. Very comfortable lodgings.
  • Reviewed October 2016
    Louise Hill

    Autumnal delight

    A fantastic week of walking in golden hued countryside, sampling local wines and enjoying local food. The group was great, the guide (Mark) top notch, the hotel and staff lovely, the organisation seamless - who could ask for more.

    What was the most inspirational moment of your trip?

    Sitting with the whole group outside a restaurant in Siena overlooking the city as the sun went down - throwing the most beautiful golden colours onto the red brick and ochre paintwork of the buildings. Idyllic.

    What did you think of your group leader?

    Mark organised us without making us feel at all "organised" and clearly knew the area well.

    Do you have any advice for potential travellers?

    Take a extra fleece if travelling in October!

Dates & Prices

An overview of flight options

Exodus is committed to making joining our tours as easy as possible, wherever you live. We generally only block book seats from London, but this certainly does not mean that you need to fly from there. Depending on the route and airlines available, there will usually be various options available for those who want to fly from their local airport.

This page aims to provide a useful overview of the options available to our clients. However, the best flight arrangements should be tailored to your personal requirements, so please contact our Sales team for expert advice.


What kind of options do I have ?

1. We can book for you: Flights from anywhere in the world - not via London  

Depending on the route, this may be direct or via an overseas hub like Amsterdam, the Middle East or elsewhere. On short haul routes there may be direct flights with low cost airlines, charter flights or scheduled airlines. Exodus can book most, but not all, of these for you. The most appropriate airline may be different to that which we use for the group flight from London, but many people now travel on different airlines and meet up with their fellow passengers at the destination.

Pros Cons
  • May be the most direct route
  • Often the extra fare compared to the London flight is minimal.
  • As you will be in the hands a single airline for your entire journey, the airline will be responsible for your bags and your connections.
  • You may not be able to join the group transfers. However, we can usually arrange private transfers, or book your flights to try and coincide with the group transfers. See notes on transfer arrangements below.


2. We can book for you: Connecting flights from your local airport to London

Exodus can book connecting flights to London so you can join the group flight there. Connecting times will be followed according to airline advice, or as requested by clients. There are two types of fares we can use for this option: a 'through-fare' or a 'published fare'.
a) A 'through-fare' is where you will be in the main airline's care throughout. You change planes, but your bags are checked all the way through to your final destination. 

b) A 'published fare' ticket is completely seperate from your onward ticket from London. It is usually cheaper than a through-fare but will need to be paid for and issued as soon as it is booked. This can be a problem if your tour has not yet reached minimum numbers. On 'published fares' neither airline is aware that you have connecting flights, so Exodus is responsible for timing your connection, not the airlines involved. The tickets are also usually non changeable and non refundable.

Pros Cons
  • Depending on the fare type, Exodus or the airline is responsible for flight connections.
  • Through fare tickets can be expensive.
  • On a published fare, tickets must be issued immediately; tickets on published fares can be very difficult to change if onward flight times change; bags are not checked though to your final destination.
  • Published fares are non-refundable.


3. Booking some or all of the flights yourself

You can also book connecting air travel yourself, either to London, or all the way to the start point. There may be certain airlines or routes we don't have access to, so this is always an option. However, if you make your own travel arrangements you become liable for any delays, cancellations or missed connections, and Exodus is not required to offer refunds if you have trouble reaching the start of your trip.

Pros Cons
  • You might find cheaper fares, or routes not available to Exodus.
  • You are responsible for any delays or missed connections, and the cost of the tour is not protected should you miss your flight be cancelled.


 Notes on transfer arrangements

Sometimes it is possible to travel on a different airline to the group flight from London. Where this is the case, we need to think about ensuring you meet up with the group with minimum extra cost and hassle.

  • On certain trips, it is easy to arrive on a different flight and still meet the group at the hotel with time in hand. We can usually arrange private transfers (at extra cost) or offer advice on taking a taxi to the start hotel.
  • On other trips (especially in Europe), the transfer meets the group flight and then travels some distance to the first night's accommodation. Where this is the case, our Sales team will try to arrange flights that arrive before (and depart after) the group. However, we do have to make it clear in your final documentation that if your flights are delayed, the transfer cannot wait for you. While Exodus or our local operators will do what we can to help you reach the start point of the tour, any additional costs must be paid by the client. 


Next steps? 

Call our Sales team on: 0203 733 0698

Email your query: [email protected]

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Call us on (354) 567 8978