Walkers in Montefioralle

Chianti Walking & Wine

8 days
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4.7 / 5 from 50 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
  • Local taxes (approx. EUR 10 per person, see Trip Notes)
Call for general departures:
020 8772 3936
Call for tailormade trips:
020 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

    Start Castellina in Chianti

    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.

    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. After lunch we enjoy a wine tasting in a local winery before heading back to our farmhouse for 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 youprebook your ticket online to avoid lengthy queues. Tickets can be purchased through https://webshop.b-ticket.com/webshop/webticket/eventlist?production=1. 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

    End Castellina in Chianti

    Trip ends at Villa Casalta.

    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. 

Summer months

Tuscany can be very hot during summer months, especially from June to August but heatwaves can happen also in April and May. During summer months temperatures can possibly reach high 30s (degC). We will try and start our walks earlier to avoid the hottest hours of the day but please be aware that temperatures and humidity will be high. You should feel comfortable and be used to walk in the heat. Agriturismo type of accommodations, as based in the countryside, are not normally equipped with air conditioning therefore rooms can be quite warm at times. Presence of mosquitos in summer may increase (significantly), we recommend taking mosquito repellent with you.

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. 

Call for general departures:
020 8772 3936
Call for tailormade trips:
020 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:
020 8772 3936
Call for tailormade trips:
020 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 October 2018
    Janice Eastman

    Wine and walking

    A well balanced holiday betwern sight seeing and walking. Excellent accommodation.

    What was the most inspirational moment of your trip?

    The organisation and diversity

    What did you think of your group leader?

    Knowledgable and professional

    Do you have any advice for potential travellers?

    Take walking boots not trainers

    Is there anything else you would like to add?

    Didnt think the cookery lesson (which was an additional extra) was worth 85 euros. Taking turns between 4 of us to knead dough was like being treated as a child. Still waiting for the receipes!
  • Reviewed October 2018
    Michelle Nogier

    Italy October 2018

    The Chianti Walking and Wine Tour was truly incredible. It was a vacation for my personal sensory system....to touch the ground that leads to...….the smell of the crisp Italian forest air, the taste of the locally sourced wine and fresh cheese, to see the vineyards, the cypress trees and the villas and to hear the sound of silence and peace, that can only be found walking the Tuscany Country. The tour was about being aware and in the moment, then taking those memories and sharing them with friends.

    What was the most inspirational moment of your trip?

    The whole trip was inspirational. For me to comprehend we walked where only the local people walked. The only other tourists were the nine people within the group and our group leader. That's it....no crowds, no noise....how much more inspirational can that be...

    What did you think of your group leader?

    Mark Middleton....super, great and loved his job. This made us enjoy the tour even more.

    Do you have any advice for potential travellers?

    From personal experience....proper hikers or really supportive runners. The walks can be more adventurous than expected.

    Is there anything else you would like to add?

    Villa Casalta is amazing - built in 1749!! Pictures and words cannot explain. Roberta and Margarita always made it feel like coming home. Absolutely loved it...
  • Reviewed October 2018
    Lynn Roulstone

    A leisurely week in beautiful Tuscany

    This holiday is ideal if you are not sure if you want a walking or a sight-seeing holiday. There are three walks, all of which are well within the capabilities of a reasonably fit person. These walks take in the vineyards, olive groves and woods of this part of Italy and also go via small towns with plenty of opportunity for good lunches or shopping. There are also visits to Sienna, Florence and San Gimignano. In the first there is a guided walk included, the second also has the choice to do a guided walk and the third is a lovely small town for wandering or looking at the frescos in the Duomo. The three wine-tastings are all very good, and there is plenty of opportunity to do more either local to the farmhouse where the trip is based or on the visits to the small towns along the way. For food lovers the meals were all very good and vegetarians are well catered for.

    What was the most inspirational moment of your trip?

    Looking at the frescos in the Duomo at San Gimignano. I was blown away by the clarity of the story-telling and the beauty of the painting. The guided tour of Sienna was excellent. There was so much packed into the three hours, included an excellent stop for coffee and cake. Castelina where the trip was based had some interesting Etruscan tombs that, despite having no artefacts remaining, are well worth a visit.

    What did you think of your group leader?

    Liz was the best driver I have come cross, ferrying us about with great efficiency. She knows the local area well so was able to fit in a quick visit to see the Leaning Tower of Pisa on the way to the airport, an unforeseen bonus. This local knowledge came in useful when suggesting things to do on our day off and during the walks, where she ensured that we were able to see lots of interesting things along the way. All together one of the best tour guides I have met.

    Do you have any advice for potential travellers?

    The walking is a little hilly, but someone with a reasonable level of fitness will not find it a problem. There are a lot of mosquitos about (and we were there late in the season) so come prepared with repellent etc. Castelina, where the trip is based, is a town well worth exploring, the Etruscan tombs are more interesting than you might think. The archaeological museum is small, but worth a visit, as the entrance fee includes being able to go to the top of the tower, where there are some excellent views. If you like ice-cream be sure to visit the gelateria in town, it is very good.

    Is there anything else you would like to add?

    I thought the tour was a good balance of sight-seeing, walking and wine-tasting. We didn't go on the Florence trip as we know the city quite well, and really appreciated a day getting to know the local area better.
  • Reviewed September 2018
    Philippa Kurys

    1st time Exodus experience

    This was our first holiday with Exodus. Usually we are independent travellers so we were both a bit nervous about a group 'organised ' trip but we needn't have worried. We had a great group of people; different backgrounds and nationalities which made for an interesting week of getting to know each other. Our fabulous guide Mark was absolutely brilliant, patient, helpful and very accommodating, keeping us out of too much sun, well watered and well informed about the various places we visited. Roberta, our host at the villa was absolutely lovely and looked after us wonderfully with the help of Margarita. We really had a great week and as well as being very impressed with our trip we've also been inspired by the experiences of Exodus from our fellow travelers; definitely food for thought for future trips.

    What was the most inspirational moment of your trip?

    We loved Siena, such a beautiful city, full of history, culture and of course wine. We really enjoyed the walking tour with Alicia, she was so passionate about her home and the history of the districts. We had a great wine school experience and just thoroughly enjoyed our day there.

    What did you think of your group leader?

    Mark was just brilliant, we really can't praise him highly enough. He really looked after us all, making various arrangements for individuals, giving us lots of local history and information and taking the time to check information and relay info after we'd returned from the trip.

    Do you have any advice for potential travellers?

    Take insect repellent as there were definitely more biting bugs than we'd anticipated. Have room in your case for wine and olive oil, managed to get 10 bottles home in total between 2 of us but there were so many lovely wines to try, you don't want to miss out.

    Is there anything else you would like to add?

    Just that we were very impressed with the whole holiday and felt it was very good value for money. We also did the cookery school on our free day which was great fun and another opportunity to meet some new people and learn about Tuscan food.
  • Reviewed September 2018
    Denise Stafford

    Beautiful Tuscany

    Wonderful week - three lovely walks through the Italian countryside and some delicious wine tasting! The wonderful Hill top towns we walked to and through were beautiful and, Siena and Florence were amazing. However, the latter was very busy, but that I suspect is due to the place.

    What was the most inspirational moment of your trip?

    Arriving at the airport in Pisa to a welcome and then meeting others in the group. I knew it would be a good week. Looking down on Florence from the car park enjoying good food, wine and company

    What did you think of your group leader?

    Our tour leader Mark was well organised, knowledgeable and made everything interesting and great fun. his attention to detail was second to none and he knew where to find the best coffee, cakes, wine, ice cream everywhere we went!

    Do you have any advice for potential travellers?

    The walking is not flat so be prepared to walk up and down hills! Mosquitos and insects abound, so some insect repellant and bit cream is a must! A liking for red wine and good food certainly helps, as does enjoying breakfast outside looking over the beautiful Tuscan hills.

    Is there anything else you would like to add?

    Great trip and would certainly recommend.
  • Reviewed September 2018
    Beth Laker

    Totally Tuscany ...

    One week of great walks , great hospitality and great food .. superb leader in Mark and combined with the warmth of the late summer sun we couldn’t ask for a better way to spend a holiday than to walk the vineyards and taste the grape 🍇

    What was the most inspirational moment of your trip?

    After a wonderful walk through working vineyards we spent an afternoon in the company of new friends in a small wine merchants shop , just us , eating Tuscan bread and cold meats drizzled with truffle oil and tasting truly glorious Turscan Chianti’s ... blissful

    What did you think of your group leader?

    Mark was a really excellent guide - just as we have come to expect with Exodus . His attention to detail and his generous spirit of care with regard to differing walking paces made him a great guide - his knowledge of the area and his quiet manner working behind the scenes to make everything run like clockwork is a credit to the Company

    Do you have any advice for potential travellers?

    Take insect repellent - the mosquitos are vicious and will find you !!!

    Is there anything else you would like to add?

    A good mix of walking and culture - with trips to Siena and Florence this tour provides interest throughout ...
  • Reviewed September 2018
    Barry Cox

    Too much Chianti in Chianti . . hic!

    This trip is a superb blend of walking, culture and fun. The villa is wonderful and in a great location a short walk from Castellina in Chianti; I especially liked the outdoors breakfast area but everything about it is so quintessentially Tuscan. The scenery is stunning and visits to Siena and Florence gave the balance of walking and culture with the bonus of the wine tastings which added the fun. The walks were well graded and much as I expected in terms of length, but there was also plenty of free time to enjoy the area. The Chianti flowed at dinner time and made for great evenings for the lovely group I was in even if some nights there was just a tad too much Chianti in Chianti!

    What was the most inspirational moment of your trip?

    Without doubt the Uffizi gallery in Florence; the gallery itself, the location with views over the city, and the art was quite breath-taking. I had to pinch myself to believe that I was standing next to a Leonardo da Vinci, Botticelli, Caravaggio or Michelangelo original. Florence itself is quite breath-taking too.

    What did you think of your group leader?

    Clearly Mark comes with much experience and he hugely enhanced the trip with his variety of much appreciated snacks on the walks, finding cheap and good coffee with clean toilets in Florence, and giving us free time in the afternoons whilst he collected the minibus to take us back to the villa. His advice on where to eat or drink was always spot on. The icing on the cake for me was Mark finding a way for me to spend the last afternoon in Pisa and visit the Leaning Tower, whilst he took my luggage to the airport. Full marks Mark!

    Do you have any advice for potential travellers?

    My calf muscles did ache on a few days so get some exercise in before you go - Tuscany is hilly! Pre-book the Uffizi to avoid the queues - I did and it worked perfectly.

    Is there anything else you would like to add?

    The villa has a great attitude to its guests consuming their own food and drink by the pool, and free tea and coffee is always available. The shower was a bit small for me but this is nit-picking in an otherwise perfect trip.
  • Reviewed September 2018
    Alan Rawlings

    Come prepared

    The walks were more challenging than we anticipated from their description

    What was the most inspirational moment of your trip?

    Finishing the walk to Radda which for us at the ages of 72 and 64 was particularly challenging

    What did you think of your group leader?

    Mark Middleton was an excellent leader and host

    Do you have any advice for potential travellers?

    For this trip make sure you get plenty of practice in particularly going uphill !!!

    Is there anything else you would like to add?

    Although at times it was hard work the trip was on the whole very enjoyable The accommodation and staff were first rate The wine was plentiful and Tuscany was stunning
  • Reviewed June 2018
    sally ashton

    excellent trip

    Wonderful combination of walks, wine , villages and cities, with a nice group of people. Weather sunny but not too hot, allowing half day hilly walks in comfort and the scenery was even better than anticipated, thanks to previous spring rain. The planning was excellent, but there was enough time to do our thing .

    What was the most inspirational moment of your trip?

    Siena. The local guide was charming and painted a lively picture of rivalry between the communities for the Palio. The Campo is stunning

    What did you think of your group leader?

    Liz was great- energetic, well organised, knowledgeable, thoughtful and fun

    Do you have any advice for potential travellers?

    We paid extra for a guided tour of Florence. The city was very crowded , and following the guide in a group was not worth the effort, though she was very (too?) informative. There is not time to view all Florence has to offer in a day. I would advise strolling round to see the Ponte Vecchio, the Duomo, the Piazza della Signoria , then a leisurely lunch followed by a visit to the Boboli and Bardini gardens. Or perhaps a week's stay in winter!

    Is there anything else you would like to add?

    My third Exodus trip. All have been great
  • Reviewed June 2018
    Malcolm Conrad

    A very enjoyable holiday!

    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.

    What was the most inspirational moment of your trip?

    The outstanding beauty of the Chianti region, in particular the magnificent views experienced on our glorious summer day's walk to San Gimignano. Also discovering a taste for the 'rooster label' Chianti wine.

    What did you think of your group leader?

    Liz Proctor our group leader was excellent. With tireless energy she worked really hard to ensure that everyone enjoyed their holiday experience to the full.

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 020 8772 3936