Classic Chianti: Florence to Siena

On this tour not only will you have the chance to explore the two great medieval cities of Florence and Siena, but you will also take walks following 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.

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.

Solo Travellers

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

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.

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.

Meals

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.

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.

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.

In order to reach Florence, you can fly into Pisa or Rome Airports. There is also an airport in Florence, however, flights in and out of this airport are limited.

From Florence, you can reach the city centre by train or bus within 15 minutes. From Pisa, you can take a special “people mover” from the airport to the Pisa Centrale Train Station and then a train to Florence. They leave every 30 mins and the journey takes approximately 1H15. From Rome, you can take a Leonardo Express Train into Rome centre and then a train to Florence. They leave frequently and the journey will take approximately 2H.

Please check the Trenitalia website for timetable planning.

From Siena it’s best to depart from Pisa or Rome Airports. There is also an airport in Florence, however, flights in and out of this airport are limited.

If departing from Pisa Airport, trains from Siena leave around every 30 mins, with one change and the journey takes approx. 1 hour 45. To reach the airport take the PisaMover from the main train station (takes 5 minutes).

Alternatively, Rome has two airports. To reach Fiumicino Airport take a train from Siena to Florence and change trains here to reach Rome central station, Roma Termini. Trains leave approximately every hour and take about 3 hours 30. From Roma Termini take another train to the airport (taking about 30 minutes). To get to Ciampino Airport there’s a bus from Roma Termini.

From Siena to Florence there are trains taking about 1 hour 30. Some trains are direct whereas others go via Empoli. There’s a shuttlebus from the centre of Florence to the airport (taking around 25 minutes). It stops beside the main railway station of Santa Maria Novella.

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.

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.