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Classic Chianti

8 Days & 7 Nights 4 Read 2 reviews
  • Walk on classic wine routes from Radda in Chianti to Siena
  • Hand-picked accommodations, all in sublime locations
  • In the heart of Chianti, sample the premium, world-class wines
  • Hike into the glorious medieval city of Siena, a Gothic open-air museum
  • Timeless and classic landscapes of vineyards, olive groves and cypresses
Follow Tuscan trails through the unforgettable wine region of Chianti to Siena, whose historic centre is a UNESCO World Heritage Site. This tour is an intoxicating mix of exceptional experiences as you walk from village to village through this striking region of Chianti. Known as Tuscany’s “third” city, after Florence and Siena, it is formed of castles, fortresses, Romanesque Churches, olive groves and row upon row of vines, interspersed with pretty wooded valleys. This alluring region has been producing world-famous velvety red wines since the 13th century and there will be plenty of opportunities during your walks to visit local vineyards and to enjoy some wine-tasting.
On this tour you follow trails through classic and timeless Chianti landscapes. It's perfect for anyone who walks regularly and wants to explore at their own pace. There are plenty of places of historic interest to discover amidst picture-postcard scenery, and many chances to visit vineyards along the way. All coupled with comfortable and welcoming accommodation, and mouth-watering food and wine. There are ascents/descents to the hill towns, due to the nature of the rolling Tuscan scenery. It’s best ahead of time to do some practice walks including stairs and ascents and descents like those you will experience on the trip whilst carrying your day bag. There are a couple optional loop walks that can be sat out if a rest day is needed. If time allows, then we’d suggest adding an additional day at the end of the trip in historic Siena to soak up the atmosphere and rejuvenate before continuing with onward travel.

Tour Type:

Slower Adventures | Where walking and cycling meet easy-going exploring, our Slower Adventures are the perfect combination. Most days are filled with picturesque journeys with some free time to dive into the destination and experience the people, local food and culture as you go.


Inn to Inn Walking | Walk from place-to-place changing accommodations each night. Generally staying in B&B’s, inns, and guesthouses.

This trip is suitable for:

Solo Travellers

As a guide, we would suggest that the minimum age of traveler this tour would be suitable for is: 12 Years

Ideal if you have an interest in:

  • Foodie
  • Wine

Activity Level & Terrain

This trip is graded ‘easy to moderate’ overall. The terrain is undulating with regular ascents and descents, and summer temperatures can be high. You should therefore be in good physical fitness to fully enjoy the walking on this tour. Most of the route follows gravel and farm tracks and trails, and minor roads from time to time. It’s best ahead of time to do some practice walks including stairs and ascents and descents like those you will experience on the trip whilst carrying your day bag. The walks are an average of 15-16 kms each day and a couple of them are optional and could be skipped if an additional rest day is required. However, should you also wish to skip a walk between towns then you will be responsible for taking a taxi or bus (if possible) to the next place.


The route is not waymarked, except for some sections on dedicated trails. However, we provide the Macs Adventure Smartphone App making it simple to follow the route using a smartphone. Rest assured that by downloading the route maps in our app, that this will continue to work even in areas without any mobile or internet reception. For extra reassurance there are also turn-by-turn route notes within the app too for the walks.


Stay in charming small hotels, guesthouses and agriturismos. We carefully select small and friendly accommodation that offers great value, so you enjoy every minute. All ae located in glorious settings, be it a town, a hamlet, or the wonderful city of Siena.

Additional Nights

Many of our walkers choose to add extra nights along the walk to sample more of the wonderful walking and attractions available in Chianti. If time allows, then we would recommend adding an additional night at the end of the tour in Siena to further explore this iconic city.

Solo Walkers & Single Rooms

This trip is available to solo walkers, although there is a supplement due to the fact that some of the costs (such as transfers) are not shared. Single rooms are available on request and a supplement is payable.


The delicious Chianti food and wine is undoubtedly a highlight of this holiday.

Breakfast is included each morning and normally consists of a traditional European style continental breakfast or buffet breakfast that often includes coffee, tea, yoghurt, granola, meat, cheese, and baked goods. In some cases, a hot dish (eggs, pancakes, etc.) will be served or offered á la carte. 

Lunches and dinners are not included in this trip. We recommend finding cafés or restaurants located in the towns or along the walking route, or to purchase snacks and a picnic lunch to bring along on the walks from local supermarkets and markets. Alternatively, most accommodations will be happy to provide a packed lunch on request and this can be booked on arrival. Dinner is available either at your accommodation or nearby restaurants. Further details can be found within your information pack and the Macs Adventure Smartphone App.

  • Accommodation in en suite rooms in charming hotels, guesthouses and agriturismos on a twin share basis
  • Daily breakfasts
  • Door to door baggage transfers as per your itinerary
  • Transfers as per itinerary
  • Access to maps, GPX tracks and daily route information with the Macs Adventure smartphone navigation app
  • All your trip documents including a detailed information pack provided digitally through your online Macs “My Account”
  • Telephone support from our offices in the event of a problem
  • Travel insurance (required) and personal equipment
  • Travel from the tour finishing point
  • Lunches, dinners, drinks, and snacks
  • Tourist taxes (charged locally at hotels)
  • Any additional transfers or public transport required to shorten the walks or skip a stage
  • Additional nights before, during or after the tour
  • Private transfer from the end point of the tour to the airport
  • Room upgrades

When To Go

This tour is available to start anytime between April and October.

Peak Season Availability

As Tuscany is a very popular destination, we suggest booking as soon as possible to ensure availability for specific dates. Availability in Siena is very difficult around the times of the 'Palio' horse races held annually normally in early July and then again in mid-August.

Time of Year

The springs months of April, May and June offer warm sunshine, fewer crowds, and pleasant walking conditions. May is when most wildflowers are coming into bloom. The autumn months of September and October are also a favourable time of year, boasting cooler weather and a striking landscape made up of autumnal colours. July and August are good months to go but can be very hot for walking and therefore aren’t best suited for everyone. You will have to start early to miss the heat of the day and carry a lot of water (additional weight) with you. Although the towns and villages are buzzing at this time of year which is great to see.

Getting to the Start

On this tour an included transfer will bring you from Siena to Radda-in-Chianti, your starting point. 

To reach Siena fly into Pisa or Rome Airports. There is also an airport in Florence, however flights in and out of this airport are limited.

If arriving at Pisa from the airport take the PisaMover to the main train station (takes 5 minutes). Turn left when exiting arrivals and the PisaMover is at the end of the airport. From Pisa Centrale Train Station trains to Siena leave around every 30 mins, with one change and the journey takes approximately 1 hour 45.

Rome has two airports. From Fiumicino Airport take a train to the central station Roma Termini (taking about 30 minutes). From Ciampino Airport there’s a bus to Roma Termini. From Rome centre change trains in Florence to go to Siena. Trains leave approximately every hour and take about 3 hours 30.

If landing at Florence Airport, there’s a shuttlebus into the centre of Florence (taking around 25 minutes). It stops beside the main railway station of Santa Maria Novella. From Florence a train to Siena takes about 1 hour 30. Some trains are direct whereas others go via Empoli.

Please check the Trenitalia website for timetable planning. Please note that not all buses/trains run on a Sunday, or they may have a reduced timetable.

Getting from the End

As the tour finishes in Siena, use the same travel information as shown in ‘Getting to the Start’ to reverse the journey back to the chosen departure point.

Luggage Transfer

One bag of up to 20kg per person will be transferred from each accommodation to the next.

At Macs Adventure, we work in partnership with many luggage transfer providers who set a limit on how many bags/suitcases they will transfer per person, and also the weight of the bag/suitcase.  Your booking includes transfer of 1 bag per person.  It is very important that you read the luggage information specific to your tour before departure. If you do not adhere to these limits, there is a great possibility that you will be charged locally both for extra bags or if they are too heavy. This limitation can be a challenge, especially as airlines generally have limits that are higher. However, our luggage providers have reasons for these limits (usually due to the Health and Safety of their employees), which we must respect.

General Information


Our pre-departure information pack details advice and a packing list on what to bring. This includes warm and cold walking gear, hiking boots, rain gear, day pack and other specifics.

Travel Insurance

It is a requirement of booking this tour with Macs Adventure that you have suitable travel insurance which covers you for the activity and emergency evacuation and hospital care.

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Day 1 Arrive in Radda in Chianti and overnight Day 2 Radda in Chianti loop walk via Castelvecchi & Volpaia Vineyards 8 miles / 13 km Day 3 Walk to Gaiole in Chianti via Vertine 9 miles / 14 km Day 4 Gaiole in Chianti loop walk via Badia a Coltibuono Monastery & Riecine Winery 9 miles / 15 km Day 5 Walk from Gaiole to Lecchi in Chianti 6 miles / 10 km Day 6 Transfer to Pievasciata or San Sano; walk to Siena 10 miles / 15 km Day 7 Free day in Siena Day 8 Onward travel from Siena

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