Chianti Walking & Wine

Name: Chianti Walking & Wine
Brand: Exodus
Rating: 4.6 (66 reviews)

Expert Local Guides

Award Winning Adventures

Nature First Adventures

Support Local Communities

8 Days from

USD 2,049

incl. Taxes

4.6/5 from

Walking & Trekking

Ways to Travel :

Guided Group, Private Group Adventures

Activity :

Walking & Trekking

Activity Levels :

2 out of 7 - Leisurely / Moderate

Group Size :

5 - 16

Ages :

18+

Trip Code :

TDC

Discover picturesque towns and delicious wines in Tuscany

With Renaissance cities, medieval villages and cypress-lined avenues winding through vineyards, southern Tuscany is the perfect place for a relaxing guided walking holiday. Based at the tranquil Villa Casalta, 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 local chianti and learn more about Italian wine on an interactive course at a wine school.

Did you know you can travel by train to this trip? Find out more here

Highlights

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

Key Information

Seven nights in a renovated farmhouse with a swimming pool
Five days gentle walking and sightseeing
Low altitude throughout
Option to travel by train to your adventure

Countries visited: Italy

What's Included

All breakfasts, five dinners, three wine tastings
All accommodation
All transport and listed activities
Tour leader throughout

What's Not Included

Travel insurance
Single accommodation (available on request)
Visas or vaccinations
Local taxes (approximately €14 per person, see Trip Notes)

5 Days of Walking & Trekking

Pace:

Leisurely/Moderate

Terrain:

Paved tracks, forest trails and gravel

Day 2

9 km / 5.6 miles

Day 3

12 km / 7.5 miles

Day 4

8 km / 5 miles

Day 6

4 km / 2.5 miles

Day 7

10 km / 6.2 miles

People, Places & Planet

We work hard to create trips that have a positive impact on the people and places we visit and look after the planet we explore. Learn more about our sustainable travel ethos and practice here and find out about the work of the Exodus Travels Foundation here.

Some sustainable travel highlights of this trip include:

People

How this trip helps improve life for local communities.

Local guides keep you well informed about local traditions and cultural-social sensitivities.
This trip brings income and opportunity to the destination community through the inclusion of locally owned hotels, restaurants, and other enterprises, and by championing locally produced food wherever possible. We spend seven nights at the family-run Villa Casalta, a farmhouse in the heart of Chianti.
We arrange three wine tastings, where we learn about local wines and how they are made. This includes a session in the farmhouse, one in a local winery and a short course at the Tuscan Wine School. These are great opportunities to support local suppliers and to encourage the traditional methods of local wine production.

Places

How this trip helps protect and conserve local landscapes and nature.

By travelling in a small group, we ‘tread lightly’ to minimise our impact on local resources and the environment.
We work with our partners on the ground to proactively reduce waste; this includes eliminating all single-use plastic water bottles by providing refills for reusable bottles.
Erosion on and adjacent to popular paths is a growing problem in certain places and therefore our trip leaders encourage clients to stick to advised routes to minimise this.
We rewild 1,075sqft (100sqm) per passenger to compensate for all trip and flight emissions.
Read about our commitment to nature protection and restoration here, including our rewilding commitment for every customer who travels with us.

Planet

How we seek to keep the carbon footprint of this trip low.

Accommodation and restaurants in the itinerary use locally sourced food which has not been transported long distances.
The farmhouse owners are environmentally conscious and try to minimise negative effects on their natural surroundings by paying attention to recycling and energy conservation.
Walking trips like this have very little detrimental impact on the environment and the locals, as it is a quiet, low impact activity requiring comparatively few resources to support.
Read about our climate action here, including our carbon reduction and compensation commitments.

Tips for sustainable travel on this trip

Leave no trace: We do all we can to ensure we leave no rubbish in the wild and beautiful places we visit; we ask that you do the same. If there are no recycling facilities in-country, consider bringing recyclable materials home with you.
Plastic waste reduction: Please bring a reusable water bottle on this trip, also consider avoiding single-use hotel toiletries, which generate a large amount of plastic waste.

Itinerary

Start at Villa Casalta, our beautiful villa 1.2mi (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

Today we head to the medieval market town of Greve in Chianti, walking through a magnificent setting of olive groves and vineyards. On the way, we stop in the fortified hilltop village of Montefioralle, considered the most ancient borgo (village) in Chianti. After lunch, we enjoy a wine tasting in a local winery before returning to our farmhouse for dinner.

Meals Included: Breakfast, Dinner

This morning, we enjoy a local history walk to the heart of the Chianti area, covering the route from Villa Casalta to Radda in Chianti. We cut through woodlands, where we can admire the emerald vineyard valleys. In the afternoon, we can taste the much-acclaimed chianti classico wine at a local winery.

Meals Included: Breakfast

After breakfast, we head to the centre of Siena for a day exploring this fascinating city. We have time to visit the numerous museums and stunning duomo (cathedral) and to relax in one of the many outdoor cafes in Piazza del Campo, home of the Palio horse race. Please note, shoulders should be covered when entering the cathedral. You may also like to visit the many boutiques specialising in local products and Italian fashion. In the afternoon, we learn about Tuscan wines on a one-hour interactive course at the Tuscan Wine School.

Meals Included: Breakfast, Dinner

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

Our destination today is Florence, birthplace of the Italian Renaissance. Most of the greats from the movement lived or passed through here: Leonardo da Vinci, Michelangelo, Sandro Botticelli and more. Learn all about it by joining one of the free local tours, which typically take in the highlights.

Join one of the morning tours and you'll have time to visit the Uffizi, an art gallery housing works by Renaissance masters, including The Birth of Venus by Botticelli and the gruesome Medusa by Caravaggio. If you do wish to visit, we recommend prebooking your ticket online to avoid lengthy queues. An ideal slot time would be around 2pm if you're joining the morning walking tour. Tickets can be purchased at www.uffizi.it/en/tickets.

Meals Included: Breakfast, Dinner

After a transfer to the quaint hamlet of San Donato, we walk through farm grounds following the pathway to Montauto and on up to the medieval town of San Gimignano. The walk is not long and should take approximately three hours. The afternoon is spent exploring this beautiful town, including visits to the Palazzo Comunale, a 13th-century stone palace that's home to the Pinacoteca (Art Gallery) and 177ft (54m) tall medieval Torre Grossa. There’s free time to wander and soak up the atmosphere.

Meals Included: Breakfast, Dinner

The trip ends after breakfast. Bid Villa Casalta a fond farewell and begin your return journey home.

Meals Included: Breakfast

Essential Info

Visa

Vaccination

Eating and Drinking

All breakfasts, five dinners and three 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.

Weather

April and May departures can expect warm days and although rain is possible, it seldom lasts long. Nights may be 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 walks, the terrain and path type include paved tracks, forest trails and gravel. The walks are not technically difficult, although there are some ascents and descents, so a reasonable amount of fitness is required. Please be aware, the Radda walk on Day 3 can be challenging due to the length and hilliness of the walk. The area is quite hilly and most drives, although short, follow twisty mountain roads through wooden areas.

Summer temperatures

Tuscany can be very hot in summer, especially from June to August but heatwaves can also happen in April and May. Temperatures can reach the high 30Cs (around 100F). We try to start our walks earlier to avoid the hottest hours of the day but temperatures and humidity will be high. You should feel comfortable and be used to walking in the heat. Agriturismo accommodations are not normally equipped with air conditioning, therefore rooms can be quite warm at times. The number of mosquitos may increase (significantly) in summer, so we recommend bringing repellent.

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.

James Nutting

Reviewed October 2022

Tourist

Well planned tour with a very professional guide

Most Inspirational Moment

Visiting Sienna

Thoughts on Group Leader

Very Professional

Tina Henderson

Reviewed September 2022

Amazing Walking & Wine Tasting in Tuscany

This holiday was everything it promised & more. The accommodation was fabulous & in a beautiful setting. 15 minutes walk from beautiful village of Castinella with a selection of shops & restaurants. The walks were well organised, taking in some amazing sights. We also really enjoyed the walking tours in Siena & Florence. Our leader, Jordan, was amazing. Informative, helpful & made everything fun. He brought the group together and we all came back having made new friends. Tuscany is stunning, the wine tastings were interesting & I would thoroughly recommend this trip.

Most Inspirational Moment

Walking the beautiful hills of Tuscany.

Thoughts on Group Leader

Jordan was absolutely fantastic. Nothing was too much trouble. He kept us informed about where & when etc & his knowledge of the area made it fun & interesting. We had a great group & Jordan brought us all together. It was a fun trip.

Advice for Potential Travellers

Just enjoy, it is such a beautiful place.

Sharon Cox

Reviewed July 2022

Chianti and Walking

An amazing holiday. Great scenery. Lovely walks. Great accommodation and lovely people. Jordan was a fantastic Tour Leader and went above and beyond. All in all, a wonderful week. Only down side was that I got bitten by mosquitoes.

Most Inspirational Moment

The whole week was lovely.

Thoughts on Group Leader

Jordan was fantastic! He went above and beyond on several occasions. He was good fun, helpful and joined us at several meals. Brilliant!

Advice for Potential Travellers

Take mosquito repellent that contains Deet. Take Piriton tablets too in case you get attacked like I did. Eat lots of ice cream! It’s fabulous!

Bina Desai

Reviewed June 2022

Tuscany hills

An amazing trip with a variety of things to do. Walking over the Tuscany hills and vineywards, tasted delicious wine, visited beautiful Florence and Sienna, so many lovely restaurants to visit. The Villa was lovely and views stunning. Spent my free day swimming and lovely lunch in the village. Dinners and breakfasts at the Villa was delicious and the wines. It was an outsanding trip.

Thoughts on Group Leader

Liz is amazing, so helpful and full of knowledge. Really looked after us all.

Advice for Potential Travellers

Bring your towel for swimming at the Villa and insect spray whilst out on walks in the summer.

Jerry Dawson

Reviewed September 2020

Fantastic trip - even more appreciated in these times of COVID restrictions!

I travelled solo on this trip departing on 12 Sept 2020, having booked it quite late as Italy was one of the few venues Brits could travel to without any COVID-related quarantine requirements either end. I was not disappointed. It is a perfect blend of walking (3 days – with fantastic views) and city tours (2 days with a guided tour of each available). Villa Casalta is a quality hotel with rooms with a view and a fabulous terrace overlooking the vineyards and skyline where all meals are eaten. The pool is also very relaxing.

Most Inspirational Moment

The walk to San Gimignano on the last day; the guided walking tours of Siena and Florence; and the session at the Tuscan Wine School in Siena. I also loved my pre-breakfast swims in the pool and the sense of peace at Villa Casalta.

Thoughts on Group Leader

Teresa did a great job and was very personable.

Advice for Potential Travellers

There is a kettle in the room - and teabags - but bring some instant coffee if you are a coffee drinker!

Suggestions

I was very impressed how this trip ran so well despite the COVID restrictions.... but don't forget to bring a face mask.

Michele Wilson

Reviewed September 2019

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.

Most Inspirational Moment

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

Thoughts on Group Leader

Teresa was excellent and came up with very good suggestions for restaurants & where to get the best gelatos!

Ronda Fogel

Reviewed September 2019

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.

Most Inspirational Moment

There was nothing inspirational about this trip.

Thoughts on 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.

Advice for Potential Travellers

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

Suggestions

Exodus needs to sort out the accommodation and food with the host. Give the tour leader more support.

Chris Nixon

Reviewed July 2019

Fabulous

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.

Most Inspirational Moment

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.

Thoughts on 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.

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.

Suggestions

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.

Martin Dennis

Reviewed July 2019

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…)

Most Inspirational Moment

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.

Thoughts on 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!).

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!

Suggestions

Book now!

Carole Grimwood

Reviewed June 2019

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.

Most Inspirational Moment

Sienna was fabulous.

Thoughts on Group Leader

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

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'.

Read All Reviews

Covid-19 refund commitment

You will get a refund if you have to cancel your trip due to COVID-19.

Availability