Hill Towns of Tuscany

Perfect for anyone who hikes regularly and wants to explore at their own pace. There are plenty of places of historic interest to discover amidst picture-postcard scenery, coupled with comfortable and welcoming accommodation and mouth-watering food and wine. There are some considerable ascents/descents (up to 520m or 1,700ft) to the hill towns at the start and end of the walks due to the nature of the rolling Tuscan scenery. It’s best to do some practice hikes ahead of time, including stairs, ascents and descents like those you will experience on the trip while carrying your day bag. However, most hikes can be shortened, and there is an optional hike that can be sat skippedif a rest day is needed. If time allows, we suggest adding a day at the end of the trip in historic Siena to soak up the atmosphere and rejuvenate before continuing with onward travel.

Classic Routes | If you’re the active, outdoorsy type, who’s interested in taking on the great routes of the world or looking for a challenge, then our Classic Routes are for you. We’re talking the West Highland Way in Scotland, the world renown Tour Du Mont Blanc and Germany's Moselle Cycle Path, to name but a few!

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

Solo Travellers, Families with Teens

The minimum age for this tour is: 12 Years

This trip is graded ‘easy to moderate’ overall, however it should be noted that the terrain is hilly and summer temperatures can be high. Most of the route follows dirt tracks and trails along with minor roads occasionally. On days 2, 4 and 5 the hiking is graded ‘moderate’ as these are more challenging days. There are options to shorten the hikes most days by joining the luggage transfer to get closer to your destination. The hike on day 6 is optional.

Stay in charming small hotels, guesthouses and an agriturismo. We carefully select small and friendly accommodation that offers great value, so you enjoy every minute.

Meals

The delicious Tuscan food and wine is undoubtedly a highlight of this vacation.

Breakfast is included each morning and normally consists of a traditional European style continental breakfast ranging from coffee, tea, yogurt, 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 hiking route, or to purchase snacks and a picnic lunch from local markets to bring along on the hikes. 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 routes are waymarked in some areas, but not in others. 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.

This tour is available to start anytime between April to October, and possibly March, but we will need to check for you that the hotels have opened for the season as several in Tuscany only open at Easter, so it depends when this falls and if they have decided to open sooner.

Peak Season Availability

As Tuscany is a very popular destination, we suggest booking as soon as possible to ensure availability for specific dates.

Time of Year

The spring 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 favorable time of year, boasting cooler weather and a striking landscape made up of autumnal colors. July and August can be very hot for hiking and therefore aren’t 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. 

The trip starts in Montepulciano. We recommend flying to Florence or Rome and transferring to their city center railway station to catch a train to Montepulciano.

If landing at Florence’s Airport (FLR): there’s a tram that departs approx. every 10min that will take you to Florence’s main railway station – the Santa Maria Novella (takes 20min).  From there you can catch a train to Montepulciano (usually changing onto a different train with a layover in Chiusi or Sinalunga). Total travel time from SMN train station to Montepulciano train station ranges between approx. 2hr15 - 3hr30, depending on train changeover time in the connecting city.

If landing in Rome (note Rome has two airports): From Rome Fiumicino Airport (FCO), take a train to the central station Roma Termini (takes about 30min). From Ciampino Airport (CIA), there’s a bus to Roma Termini (takes about 40min). From there you can catch a train to Montepulciano (usually changing onto a different train with a layover in Chiusi or Siena). Total travel time from Roma Termini train station to the Montepulciano train station ranges between approx. 2hr15 - 3hr30, depending on train changeover time in the connecting city. If you would prefer not to wait for the connecting train in Chiusi, we can arrange a car transfer to your hotel (additional costs apply). You also have the option to arrange a taxi on your own.

Train timetables are available at Trenitalia.

Montepulciano is on a minor rail line and the station is a few km/miles outside of town. We have included a transfer from this train station to your accommodation in town.

As soon as possible after booking your train ticket, notify Macs what time you will arrive at the Montepulciano Train Station so that we can arrange your included transfer accordingly.

Alternatively, if you’d rather not use the included transfer from Montepulciano Train Station, you may wish to instead take a taxi or the bus that runs from Chiusi Train Station to Montepulciano Bus Station. The journey is about 25 minutes and payable locally. Please let us know if you don’t require the transfer.

Please note that not all buses run on a Sunday, or they may have a reduced timetable.

If you’d prefer to avoid public transport to Montepulciano, a private transfer can be requested. Please let us know at the time of booking if you would like to add this option (addtional costs apply). 

From Siena take the train back to Florence, Rome, or Pisa. Once again it will be necessary to travel from the central stations in these cities back to the airports (see ‘Getting to the Start’ for further information about this). Please see Trenitalia’s website for timetables.

Approx. total journey times from Siena are:

To Florence 2hr15 - 3hr15

To Rome 2hr15 - 3hr20

To Pisa 2hr00 - 3hr15

Siena Train Station is in the valley below the city centre and there are escalators between the two or there are local buses.

To Florence Santa Maria Novella there is usually a direct train that goes via Empoli and takes around 1 hour 30.

To Roma Termini in Rome it’s normally necessary to change trains in Chiusi-Chianciano Terme.

To Pisa there is usually a direct train that goes via Empoli and takes around 1 hour 40.

One bag of up to 20kg/44lbs 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.