Hill Towns of Tuscany

8 Days & 7 Nights 4.5 Read 48 reviews
  • Explore the famed hill towns of Southern Tuscany on foot
  • Scenic walks between Renaissance and medieval towns, vineyards, and olive groves
  • Relax and recharge in the thermal baths at Bagno Vignoni
  • Time to reflect and listen to the sound of monastic chants in Sant’ Antimo Abbey
  • Fantastic cheese, pasta, and wine including Brunello di Montalcino and Nobile di Montepulciano
Explore Tuscany’s timeless rolling scenery, walking between Renaissance and medieval hilltop towns, before arriving in iconic Siena. The journey winds through a unique linear, almost geometric landscape of hills, vineyards, and olive trees. Highlights include the historic spa baths at Bagno Vignoni and the Romanesque Sant’ Antimo Abbey. Follow rewarding trails through the lesser-known wine regions and join the Via Francigena pilgrimage path for part of the journey. Take time, slow down and discover the tastes and textures of Tuscany, one of Italy’s most iconic regions.
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. All coupled with comfortable and welcoming accommodation, and mouth-watering food and wine. There are ascents/descents to the hill towns at the start and end of the walks, 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. However, most walks can be shortened and there is an optional walk 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, 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 and, minor roads occasionally. On days 2, 4 and 5 the walking is graded more towards the ‘moderate’ side as these are more challenging days. There are options to shorten the walks most days by joining the luggage transfer to get closer to your destination. The walk on day 6 is optional.


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. For extra reassurance there are turn-by-turn route notes within the app too for the majority of 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.

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 Tuscany. We would recommend spending extra nights in Pienza, Montalcino and/or Siena. Please notify us at the time of booking should you wish to add extra nights.

Single Rooms & Solo Walkers

This trip is based on double occupancy (two people sharing a room with one bed). If separate rooms are required, then a single supplement is payable. If a twin room is needed (same room with two separate beds), please notify us at the time of booking so we can request this option. This trip is available to solo walkers.


The delicious Tuscan 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 ranging from 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
  • Transfer as per your itinerary
  • Door to door baggage transfers as per your 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 and local partner in the event of a problem
  • Travel insurance (required) and personal equipment
  • Lunches, dinners, drinks, and snacks
  • Tourist taxes (charged locally at hotels)
  • Travel to and from start and finish points
  • Any additional transfers or public transport required to shorten the walks or skip a stage
  • Additional nights before, during or after the tour
  • Private transfers to the start and from the end points of the tour
  • Room upgrades

When To Go

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 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

We recommend flying to Florence, Rome, or Pisa and catching the train from the city centre railway station to Montepulciano (usually changing in Chiusi).

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.

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.

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.

Montepulciano is on a minor rail line and the station is a few kilometres outside of town. We have included a transfer from the train station to the town centre. We need you to advise us as soon as possible after booking as to which train you will be arriving on in order for the transfer to be arranged accordingly.

Alternatively, if you’d rather not use the included transfer from Montepulciano Train Station then rather than getting off the train in Montepulciano there are buses that run from Chiusi Train Station to Montepulciano Bus Station or you can take a taxi. The journey is about 25 minutes. Please let us know if you don’t require the transfer.

Approx. journey times to Montepulciano are:

From Florence 1hr50 - 2hr15

From Rome 1hr50 - 3hr15

From Pisa 2hr50 - 3hr20

Train timetables are available at Trenitalia. Please note that not all buses run on a Sunday or they may have a reduced timetable.

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).


Getting from the End

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.

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

The distances and ascent/descents are approximations of the recommended routes. Please be prepared by packing all necessary items, for example, proper rain gear (jacket and pants), sun hat, sunscreen. Your information pack has a detailed equipment list which includes standard walking gear such as good walking boots or shoes, warm and waterproof clothes for the cooler months and lightweight clothing for summer, and a day pack.


The tour information pack has a detailed equipment list which includes standard walking gear such as good walking boots or shoes, warm and waterproof clothes, and a day pack.

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.

How fit do I need to be?
How far in advance do I need to book?
What equipment do I need?
What happens if I can’t walk a stage?


Day 1 Arrive in Montepulciano, transfer to the town centre Day 2 Walk from Montepulciano to Pienza 9 miles / 15 km Day 3 Walk from Pienza to Bagno Vignoni Thermal Baths 9 miles / 14 km Day 4 Walk from Bagno Vignoni to Sant’ Antimo Abbey; transfer to Montalcino 8 miles / 13 km Day 5 Walk from Montalcino through the Crete Senesi to near Buonconvento 10 miles / 16 km Day 6 Walk from Monte Oliveto Maggiore Monastery to near Buonconvento 6 miles / 10 km Day 7 Transfer to Grancia di Cuna Medieval Farm; walk to Siena 10 miles / 16 km Day 8 Onward travel from Siena

The Macs Way

  • Tried & Tested Adventures Tried & Tested Adventures
  • Freedom Freedom
  • Book with Confidence Book with Confidence
  • Expertise Expertise
  • Positive Impact Positive Impact
Built with our expert knowledge, to suit you.
  • Knowledgeable and helpful specialist trip planners
  • Wide variety of tours to suit all interests and experience levels
  • Start on any date that suits you
  • Choose your ideal trip length and difficulty
  • Range of accommodation comfort levels
  • Choice of trip styles
Authentic adventure travel experiences on your own terms
  • Choose your own travel companions
  • Walk, cycle and explore at your own pace
  • Make your own decisions
  • Choose your own path
  • Indulge your passions
Feel secure in making the right choice for your precious adventure time
  • 18,000+ unbiased trip & service reviews
  • Feefo Platinum Award 2023
  • 25,000+ travelers trust us each year
  • As featured in the Guardian, Times, Nat Geo Traveler
  • Founder owned & operated since 2003
  • 100+ passionate team members across the US, UK & Europe
You can be confident that every detail of your journey has been expertly planned
  • Carefully planned adventures
  • Quality, hand-picked accommodations
  • Seamless and reliable arrangements
  • Comprehensive trip information & insider tips
  • Detailed maps, route notes and mobile GPS app
  • Helpful 24/7 support should you need it
Travel the right way and make a positive impact
  • Travel responsibly
  • Explore off the beaten track
  • Support locally owned businesses
  • Engage with local communities
  • Minimize your impact
  • Maximize the benefit of your travel
  • Challenge yourself & grow
$ - USD - US Dollar
Country/Region name: