Walkers in Montefioralle

Chianti Walking & Wine


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8 days
incl. taxes
4.6 / 5 from 61 reviews
Walking & Trekking
Suitable for:
Age 18+
Activity level:
Leisurely / Moderate
Activity Rating - Leisurely/Moderate
Trip code: 
Way to Travel:
Guided Group
Walking & Trekking
Group size:
Min age:

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
  • Countries visited: Italy

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:
1 800 267 3347
Call for tailor made trips:
1 800 267 3347
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

Tourism can be a real help to local communities, providing income, positive cultural exchanges and a financial incentive to protect their natural environment. Ours is a 'total approach' to responsible tourism, covering everything from the way we plan and operate our trips to the practices of Exodus as a company. 

On this trip, we spend the nights in Villa Casalta, a family run farmhouse in the heart of Chianti. Where meals are provided, ingredients used are locally sourced and follows local traditional recipes wherever possible. This ensures that our visit is benefitting the local communities. The owners are conscious of their environmental impact and tries their best to minimise it as much as possible through efforts to recycle and conserve energy within the property. 

The wine tasting sessions arranged are a great opportunity to support local producers and promote the traditional methods of local wine production. Walking trips have very little detrimental impact on the environment and local residents as it is a quiet, low impact activity requiring comparatively little resources to support.

In March 2019, Exodus Travels launched the Exodus Travels Foundation where we support initiatives all around the world. But it cannot exist without travellers who care. Get involved or learn more about what Responsible Travel means to Exodus 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.

    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 https://webshop.b-ticket.com/webshop/webticket/eventlist?production=1

    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




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. 

Following a review of all our trips we have categorised this trip as generally not suitable for persons of reduced mobility. However if you are a regular traveller on such trips, please contact customer services to discuss the trip and your personal condition.

Call for general departures:
1 800 267 3347
Call for tailor made trips:
1 800 267 3347
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. 

Please note that on some of the earliest departures (in April) and latest departures in October, we may use an alternative accommodation: Albergo Il Colombaio - located within a short walking distance to the town of Castellina in Chianti and it offers the same facilities and standards as Villa Casalta. We have used this property on previous trips and received very positive feedback. 

Call for general departures:
1 800 267 3347
Call for tailor made trips:
1 800 267 3347
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

  • Reviewed September 2019
    Michele Wilson

    Lovely group

    I had a wonderful holiday with a fun group of people. Our leader Teresa & Mike the driver ( who also walked with us) organised everything brilliantly and were very patient walking at the perfect pace. The Tuscan countryside is breathtaking, as are the beautiful hilltop villages and towns. The only downside was the food at our accommodation, which was poor. On the plus side the food in the local restaurants chosen by Exodus was delicious. The wine tasting was great and very informative.

    What was the most inspirational moment of your trip?

    The last day walking through the beautiful undulating hills and vineyards to San Gimignano.

    What did you think of your group leader?

    Teresa was excellent and came up with very good suggestions for restaurants & where to get the best gelatos!
  • Reviewed September 2019
    Ronda Fogel

    It promised so much ...

    Unfortunately Exodus dropped the ball on this particular tour. A combination of a new inexperienced tour leader, dirty poorly maintained accommodation (Agriturismo is not an excuse for dirty or poorly maintained accommodation!) and inedible food. My expectation of the actual tour itself was different from the reality. No transport to and from town on days off.

    What was the most inspirational moment of your trip?

    There was nothing inspirational about this trip.

    What did you think of your group leader?

    It was our group leader's second tour in the area. He was inexperienced and lacked local knowledge, at times he seemed overwhelmed.

    Do you have any advice for potential travellers?

    Don't go! There are far better tours on offer than this one.

    Is there anything else you would like to add?

    Exodus needs to sort out the accommodation and food with the host. Give the tour leader more support.
  • Reviewed July 2019
    Chris Nixon


    A fabulous combination of walking the Tuscan countryside, combined with wine tastings and city visits. Alejandro was a brilliant leader. Villa Castalta is a perfectly adequate base for a walking holiday. The meals at the Villa are basic but wholesome. The restaurant used in the village were all different and very good. The best being Il Re Gallo. The 3 main walks are all interesting, each finishing in an interesting town for lunch and gelato! Despite the high temperatures during our week (highs of upper 30s) all the walks were at a a relaxed pace with plenty of stops along the route.

    What was the most inspirational moment of your trip?

    The trip to Siena was excellent, with a very good guide in Sara. It was great to find out about the history of the city and the different districts. During our visit, they were preparing for the Palio, which added to our interest. The visit to the Tuscan Wine School in the afternoon was very informative. This did not take anything away from the other city visit to Florence, where we had another excellent , but different type of guide, Elizabetta, who told us about the history of Florence with great charm and wit.

    What did you think of your group leader?

    Alejandro was fantastic. The walks were well paced and we had sensible early starts, considering the heat. He was very informative about the flowers and trees along the route. And feed us cherries and white mulberries. His choice of restaurants in Castellina was excellent.

    Do you have any advice for potential travellers?

    As others have remarked, good walking boots or shoes are advised for the hill walks. Plus you will need long trousers on the first part of the walk to Radda. (Read the trip notes!) A torch is useful for walking back from Castellina at night.

    Is there anything else you would like to add?

    If you want a walking holiday combined with visits to Siena and Florence, this is the trip to go on.You also learn about Chianti and experience varying types of Italian food.
  • Reviewed July 2019
    Martin Dennis

    One of the best...

    For me, there are three criteria that make a great Exodus trip: the members of the group, the leader, and the location/activities. The members of the group on this trip were wonderful: great company, entertaining, and considerate. Mark was the perfect leader (see below). The location was stunning with beautiful Tuscan villages, towns and cities. How can the combination of wine and walking be beaten? (OK, maybe cycling and wine at a push...)

    What was the most inspirational moment of your trip?

    So many: approaches to archetypal Tuscan villages; stunning views of Florence, San Gimignano and Siena. Hearing scops owls and nightingales (why are both so difficult to spot?!). Wonderful food and wine.

    What did you think of your group leader?

    The perfect guide: helpful, knowledgeable, considerate, funny, flexible and an exemplary driver (reversing with trailer into a space at Pisa airport, first time and in front of an audience!).

    Do you have any advice for potential travellers?

    Take a bigger case to accommodate the chianti, cheese, olive oil you'll want to bring back. I didn't buy dresses or handbags but some did!

    Is there anything else you would like to add?

    Book now!
  • Reviewed June 2019
    Carole Grimwood

    Excellent trip - But a bit more than gentle walking

    We had a great of walking and wine tasting in the Chianti region with our excellent guide Alejandro. Our accommodation at Villa Castela was probably the best we have enjoyed with Exodus - great location, tranquil, lovely pool, big room, comfy bed and simple but delicious food.

    What was the most inspirational moment of your trip?

    Sienna was fabulous.

    What did you think of your group leader?

    Alejandro was an excellent hard working guide who went the extra mile

    Do you have any advice for potential travellers?

    We were 'blessed' with very hot weather in early June (high 30s and 37 deg on our last day) which made some of the very undulating walking hard work for us and definitely not 'gentle'.
  • Reviewed June 2019
    Gill & Don Yuile

    Our first Exodus trip

    This trip met all our expectations and requirements and was a really good holiday for us. The daily organisation and all the experiences were excellent, we cannot praise Liz enough for her competence at making the week so good. The walks were amazing, just at the right level for us and we felt spot on with the leisurely/moderate rating. The hotel was beautifully situated, traditionally furnished, clean and homely, the staff were very nice, helpful and pleasant. Just a few quibbles that have prevented us awarding the top rating: the hotel breakfast was good, although a bit more variety would have been nice, but the evening meals taken in the hotel were fairly basic. The meals taken outside in local restaurants were fantastic. Our pre trip information supplied from Exodus gave us the wrong departure terminal at Heathrow, which we realised just two days before departure, however, this was dealt with efficiently and we appreciated how well it was handled. All in all an excellent week, we enjoyed it immensely and are looking at our next adventure!

    What was the most inspirational moment of your trip?

    Probably the best thing about this trip was the ratio of walking, city visits and wine tasting. A perfect amount of each meant that it was all most enjoyable.

    What did you think of your group leader?

    Liz was a fantastic guide in all ways: leader experience, local knowledge, language skills, driving, organisation, and making sure every member of the group was comfortable and any special requirements taken care of. She was nice with it!

    Do you have any advice for potential travellers?

    We recomend taking walking boots rather than trainers for the walk days as many of the tracks have loose stones and rocks. Flat shoes recomended for the rest of the time, especially in towns and cities.
  • Reviewed June 2019
    Debbie Henderson

    Fantastic Holiday

    I'd wanted to go to Tuscany for years and this exactly fitted the bill. Wonderful walks, hilltop towns, visiting Siena, Florence and San Gimignano. Wine tastings were informative. Lovely group too. I can definitely recommend!

    What was the most inspirational moment of your trip?

    Seeing the fabulous scenery at every turn!

    What did you think of your group leader?

    Mark was a great leader: fun, courteous, always ready to help out and a very safe driver.

    Do you have any advice for potential travellers?

    The walks can be a bit more of a challenge in the heat...but don't let that put you off.
  • Reviewed May 2019
    Jan Strasser

    A Great trip to celebrate a milestone birthday!

    We had a fantastic time with a great group of people walking along the beautiful hills of Tuscany - visiting quaint hilltop villages - viewing spectacular scenery and partaking in wonderful food and wine

    What was the most inspirational moment of your trip?

    Hard to name just one! I loved the hilltop villages but I also love Florence - something incredible to see around every corner!

    What did you think of your group leader?

    Liz Proctor was our group leader and she is amazing! She knew so much about every single place we visited.

    Do you have any advice for potential travellers?

    If you enjoy walking and great food and wine I highly recommend this trip
  • Reviewed May 2019
    Jane Jewell

    First trip with Exodus

    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 evening.th

    What was the most inspirational moment of your trip?

    The beautiful Tuscan countryside and the Agritourism which has enriched the Tuscan landscape and allowed the families to develop their hardworking but enriching way of life. The natural ecological way of living which is a model of living to aspire to.

    What did you think of your group leader?

    Excellent, very personable, calm and extremely knowledgeable. As well as acting as a extremely competent driver as well as the guiding. We really appreciated the good planning and timing that went into everyday and we trust that Liz is remunerated fully for this double role and responsibility.

    Do you have any advice for potential travellers?

    Read fully the excellent guidance notes sent by Exodus

    Is there anything else you would like to add?

    A truly varied and enjoyable trip in a beautiful country with lovely warm people. We also thoroughly enjoyed the Cooking day we booked on our day off.
  • Reviewed April 2019
    Helen Stevenson

    Wonderful trip!

    The countryside walks were paced perfectly, with time at the end of each to visit beautiful hilltop towns for leisurely lunches and sightseeing . Visits to Siena and Florence provided a taster for these beautiful cities. The wine tasting, particularly the Siena Wine School, was enjoyable, as was the Chianti imbibing throughout the week. Everything at Villa Casalta was very relaxed, owner and her staff friendly and helpful. I appreciated the tea and coffee making facilities set up in the sitting room for Exodus customers. I loved having day off mid week when I spent a leisurely day in Castellina.

    What was the most inspirational moment of your trip?

    No single moment as I enjoyed it all.

    What did you think of your group leader?

    Liz Proctor is brilliant in every way - friendly, enthusiastic, knowledgeable, helpful, and more...

    Do you have any advice for potential travellers?

    To book a time slot for Uffizi Gallery the trip notes suggest between 11.45 and 16.00. Liz has discovered a very good free walking tour of Florence 10.30 to 13.00, which I had to leave at noon. Also 4pm is too late as it's a minimum half hour walk back to the bus for 5pm. I suggest around 2pm would be ideal time slot. I was pleased I took walking poles and used them on all the country walks.

Dates & Prices

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