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. 

This trip starts in Montepulciano and includes a transfer from the Montepulciano Train Station (which is located a few km/miles outside of town) to your hotel. To reach Montepulciano, we recommend flying into Rome Airports (FCO or CIA) or Florence (FLR), however, flights in and out of this airport are limited. You can also arrive at the Pisa Airport (PSA), but you'll want to take the train to Florence in order to make your way to Montepulciano. 

If arriving in Florence: 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, there are trains 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. 2H15 – 3H30, depending on train changeover time in the connecting city.

If arriving in Pisa: From the airport take the PisaMover that departs approx. every 10min to the Pisa Centrale Train Station (takes 5 minutes). After exiting Arrivals, follow the signs for the PisaMover, turning left and walking along the passageway to the little Pisamover station at the end of this passageway. You can either take the stairs up or go up to the platform with the elevator. Once upstairs you can buy a ticket from the machine. From Pisa Centrale Train Station, trains to Florence leave around every 30min, and the journey takes approx. 1H15. From there, you'll want to follow the instructions for traveling to Montepulciano from Florence.

If arriving in Rome (note Rome has two airports): From Rome Fiumicino Airport (FCO), take the Leonardo Express Train that’s located inside the airport and departs every 15min to the central train station Roma Termini (takes about 32min). From Ciampino Airport (CIA), there’s a bus to Roma Termini (takes about 40min). From Rome’s Roma Termini Train Station, there are trains 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. 2H15 – 3H30, 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.

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.

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 choose 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 is payable locally. Please let us know if you don’t require the included transfer.

If you’d prefer to avoid public transport from the airport, a private transfer can be requested. Please let us know at the time of booking if you would like to add this option (additional costs apply). Once your trip is confirmed please share your flight information with us, including your arrival time, as soon as you have booked your flights, so that we have those details well in advance and we can arrange the transfer for you ahead of time. 

It's easy to travel from Siena by train to the major airports of Florence, Pisa, and Rome.

The Siena Train Station and Bus Station are located in the valley below the city center. (about a 2km/1.25mi walk from the majority of accommodations we use). To make your way to the station you have a few options (each payable locally): 1) take the escalators 2) take a bus or 3) take a taxi.

Approx. total journey times from Siena are:

To Florence 2H15 – 3H15

• The train to Florence Santa Maria Novella station is usually a direct train that goes via Empoli and takes around 1H30. Some trains are direct whereas others go via Empoli.

To Rome 2H15 – 3H20

• To Roma Termini Train Station it’s normally necessary to change trains in Florence or Chiusi-Chianciano Terme and takes around 3H30.

To Pisa 2H00 – 3H15

• To Pisa’s Train Station there is usually a train that departs approx. every 30min that goes via Empoli and takes around 1H45.

Once again it will be necessary to travel from the central train stations in these cities back to the airports (see ‘Getting to the Start’ for further information about this).

Alternatively, we can arrange a taxi from Siena to your departure city or airport. Please let us know in advance if you wish to include this option for an additional fee.

Please check the Trenitalia website for timetable planning. There are also local buses that you can take for your onward travel and you can find the information here. Please note that not all buses/trains run on a Sunday, or they may have a reduced timetable.

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.