Sign Up

After creating an account, you'll be able to track your payment status, track the confirmation and you can also rate the tour after you finished the tour.
Confirm Password*
First Name*
Last Name*
* Creating an account means you're okay with our Terms of Service and Privacy Statement.

Already a member?



Sign Up

After creating an account, you'll be able to track your payment status, track the confirmation and you can also rate the tour after you finished the tour.
Confirm Password*
First Name*
Last Name*
* Creating an account means you're okay with our Terms of Service and Privacy Statement.

Already a member?


Adding item to wishlist requires an account

Chianti Walking & Wine Week-Long Tour

Min Age : 18
Inquiry Form×
Full Name*
Email Address*
Phone Number*
Your Enquiry*
Booking Form×
The tour is not available yet.

Instant Book


Discover picturesque towns and delicious wines in Tuscany

With its Renaissance cities, medieval 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, the tour visits 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 you’ll 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.

There is also a more-intense set of Wonderful Day Walks Through Tuscany’s Idyllic Mountains available.

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

Day 1Start Castellina in Chianti

Start at Villa Casalta, a beautiful villa 1 1/4 miles from Castellina in Chianti. In the evening the guide will hold a welcome meeting to discuss the week ahead, give advice on the local area and answer any questions.

Meal included: dinner

Day 2Medieval market town, hilltop village, afternoon wine tasting

Today you head to the medieval market town of Greve in Chianti walking through a magnificent setting of olive groves and vineyards. On the way, you 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 the farmhouse for dinner.

Meals included: breakfast dinner

Day 3Walk to Radda in Chianti

This morning you 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. You will take a walk through local woodlands where you can admire the so famous emerald vineyards valleys. In the afternoon you will have the chance to taste the much acclaimed Chianti Classico wine at a local winery.

Meal included: breakfast

Day 4Travel to Siena, learn about wine at the Wine School

After breakfast you make our way to the center 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 youalso 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 5Free 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 day trips.

Meal included: breakfast

Day 6Magnificent city of Florence, birthplace of the Renaissance

Your 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 center 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.

Meals included: breakfast dinner

Day 7Walk to picturesque San Gimignano

After a transfer to the quaint hamlet of San Donato, you 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 8Final Good-Byes

Your trip will end at Villa Casalta in Chianti.

Meal included: breakfast

What's Included

All breakfasts, 5 dinners, 3 wine tastings

All accommodation

All transport and listed activities

Tour leader throughout

Not Included


Travel insurance

Visas or vaccinations (if required)

Single accommodation (available on request)

Local taxes (approx. EUR 10 per person)

Q & A

How strenuous is this tour?

This trip is graded Activity Level 2 (leisurely). 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 man-made paved tracks, streets, 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.

What is the hotel like?

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 of 2020 season, for logistic reasons, in terms of accommodation you may stay at: Albergo Il Colombaio, located within a short walking distance to the town of Castellina in Chianti and offering the same facilities and standards as Villa Casalta. 

Is there a single supplement?

Where a single supplement is available, paying for a single only guarantees a room for single use. It does not always mean a twin or double room will be provided for sole occupancy. Single supplement starts at $484.50

What is on the menu?

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.

What must I bring?

  • Light walking boots (a pair of good walking trainers will suffice)
  • Small daypack for camera
  • Refillable water bottle
  • Sunscreen
  • Swimwear
  • Hat
  • Sunglasses
  • Warm clothes
  • Electrolyte sachets (to put in water during summer months)
  • Insect repellent (in summer months there might be mosquitoes, horse fly and wasps)
  • Long trousers for some walks as ticks may be present in the woodland

Is this responsible tourism?

Tourism can be a real help to local communities, providing income, positive cultural exchanges and a financial incentive to protect their natural environment. On this trip, you 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 your visit is benefiting the local communities. The owners are conscious of their environmental impact and tries their best to minimize 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.

Availability Calendar

8-Day Trip | Depart September 5, 2020 $1679

8-Day Trip | Depart September 12, 2020 $1679

8-Day Trip | Depart September 19, 2020 $1679

8-Day Trip | Depart October 3, 2020 $1649

8-Day Trip | Depart October 10, 2020 $1549

Terms & Conditions

Tour run by Exodus Travels. Order of activities and paths subject to change depending on number of groups booked each week. Departures will be guaranteed to go ahead once it reaches minimum numbers. Adequate and valid travel insurance is compulsory for all Exodus travelers and it is a condition of accepting your booking that you agree you will have obtained adequate and valid travel insurance for your booking. We recommend you take out insurance as soon as your booking is confirmed. You will need to pay a deposit at the time of booking of at least 10% per person of your selected travel arrangements (minimum $300 per person or equivalent). 

Cancellation policy:

More than 70 days before departure date: Loss of deposit unless booking (and deposit) is transferred to a new booking within 12 months of the date the original booking was canceled.

Between 70 and 42 days before departure date (inclusive): 50% of the holiday cost

Between 41 and 28 days before departure date (inclusive): 60% of the holiday cost

Between 27 and 15 days before departure date (inclusive): 80% of the holiday cost

14 days or less before departure date (or failure to join the holiday) (inclusive): 100% of the holiday cost


Sign up today and be the first TO BE FIRST

Special members only offers

Hand picked vacations & wellness news just for you

Wellness travel tips & advice

Travel inspiration




Lorem ipsum dolor sit amet, consectetur adipiscing elit.

Thank you for subscribing!