Tuscany: Hilltop Towns | Walking Tour, Self Guided

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.

What To Expect

Travel restrictions and resources, to and from any destination

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 Style:

Self Guided | Go at your own pace on an independent tour.

Activity:

Multi Center Walking | You will spend multiple nights in one or more of the locations on this walking tour

This trip is suitable for:

Solo Travelers, Multi-Generational, First Timers

Ideal if you have an interest in:

Foodie Adventures
Wine, Whiskey & More...
Wellness & Spa
Historical Journeys
Special Occasions

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.

Navigation

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.

Accommodations

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.

Meals

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.

Included

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

Excluded

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

Extras

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 March to October.

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

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.

Equipment

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.

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Itinerary

Day 1 Arrive in Montepulciano, transfer to the town centre Day 2 Walk from Montepulciano to Pienza 9 miles / 15 km

Leave Montepulciano through one of the historic gates before heading out into the surrounding countryside. From the San Biagio Church, follow a quiet trail pass vineyards and olive groves to the peaceful village of Montichiello. Why not pause here for a relaxed lunch or perhaps just a quick cappuccino before continuing to the hilltop town of Pienza.

Pienza is a UNESCO World Heritage Site with unique Renaissance architecture. The town is well known for its delicious pecorino cheese and truffles; this is a great spot to indulge in Tuscan treats!

For anyone wanting to take an easier walk today it’s possible to transfer to Montichello and walk from here to Pienza.

Shorter walk from Montichiello: 6kms/4mi Ascent/Descent: 472m/522m

Walk from Montepulciano: 15kms/9mi Ascent/Descent: 472m/522m

Overnight Pienza

Accommodations

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Hotel Corsignano | 4 Star | Hotel

Recently renovated the Hotel Corsignano is a newly certified a “Green” Hotel. This beautiful 4- star Hotel is beautifully furnished and extremely comfortable, set in the frame of Tuscany's most beautiful and unspoilt area, reaching from Pienza to the Orcia-Valley.

Hotel Residence San Gregorio | 3 Star | Hotel

Hotel Residence San Gregorio is situated a few hundred meters away from the ancient walled town of Pienza, in the heart of Tuscany. It offers an ideal exclusive environment to spend a night or a few days immersed in the magical atmosphere of a renaissance town, considered to be an architectural jewel.

Hotel Rutiliano Pienza | 3 Star | Hotel

This small hotel is set in a quiet position, surrounded by a peaceful garden and yet just a few steps from the historic town centre. There is an outdoor swimming pool with sun loungers and deckchairs to relax on. In the warmer months breakfast is served outside on the terrace. There is a wellness centre with Turkish bath, sauna, and treatments available (additional costs apply). There is also a bar and breakfast room. The comfortable bedrooms are equipped with air conditioning.

Day 3 Walk from Pienza to Bagno Vignoni Thermal Baths 9 miles / 14 km

This is a particularly great walk as most of the time it’s possible to see both where you've been and where you are aiming for. Setting out on the walk from Pienza; admire the views across the valley with its typical Tuscan scenery of cypress trees, rolling farmland, and olive groves. Along the way stop in San Quirico d'Orcia. A walled town with an elegant 12th century church and ornate gardens. It is a great place to spend some time exploring.

Pass through Vignoni with its iconic stone tower before arriving in the spa town of Bagno Vignoni. The thermal baths complex is the perfect location soak up the Tuscan warmth and relax after a day’s walking.

For anyone wanting to take an easier walk today it’s possible to transfer to San Quirico d'Orcia and walk from here to Bagno Vignoni.

Shorter walk from San Quirico d'Orcia: 5kms/3mi Ascent/Descent: 311m/488m

Walk from Pienza: 14kms/9mi Ascent/Descent: 311m/488m

Overnight Bagno Vignoni

Accommodations

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Hotel Albergo Le Terme | 3 Star | Hotel

Surrounded by the warm steam from the thermal spring, continuing the legend of healthy water, one finds the ancient construction of the Rossellino, home of Pope Pius II Piccolomini, today known as the Hotel "Le Terme". The rooms are decorated in classical style and the restaurant specialises in traditional Tuscan style food where simple ingredients are combined into delicious dishes. All complimented by delicious wines from the surrounding villages.

Osteria dell'Orcia | 4 Star | Hotel

Hotel Relais Osteria dell’Orcia occupies a finely restored 16th century horse and carriage station, located along the Via Francigena, in the vicinity of Bagno Vignoni, where, in centuries past, pilgrims from Northern Europe traveling to Rome regularly sought rest and refreshment.

In the late 1990’s, Hotel Osteria dell’Orcia Relais became the subject of an extensive restoration project, which successfully reinstated the building’s original charm and, at the same time, allowed for the careful integration of the latest in modern comforts and technology

Today’s Hotel Osteria dell’Orcia Relais is an intimate, four star establishment, providing quality guest accommodation in just 16 bedrooms, each of which is individually furnished in romantic Tuscan country style.

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

Walk through the famous Brunello wine region, passing vineyards and olive groves, before entering the Tuscan landscape of the “Crete Senesi” with its rolling hills and farmland, dotted with patches of woodland and quaint little villages. The walk finishes up at Fattoria Pieve a Salti Agriturismo near Buonconvento. Our characterful accommodation is the ideal spot to relax after a long walk, alternatively why not explore a bit more and visit nearby Buonconvento. This photogenic village is still nearly entirely surrounded by the ancient city walls with only a small section being destroyed in World War II. There’s also a pretty little church and two small museums here - Religious Art Museum of the Val d’Arbia and the Museum of Sharecropping.

Alternatively, there is an easier walking option today, which is slightly shorter and is a gentle downhill route into Buonconvento village. Spend some time exploring here before transferring to Fattoria Pieve a Salti.

Shorter walk to Buonconvento: 12kms/7mi Ascent/Descent: 43m/396m

Walk to Pieve a Salti: 16kms/10mi Ascent/Descent: 277m/522m

Please note that on the rare occasions that the Fattoria Pieve a Salti Agriturismo is fully booked the accommodation will instead be in a small hotel centrally located in Buonconvento. In which case it will be the shorter walking option used today.

Overnight Buonconvento

Accommodations

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Fattoria Pieve a Salti | 3 Star | Agriturismo

Fattoria Pieve a Salti is an agriturismo that has been converted from restored farm ruins into a stunning country hotel complex including a swimming pool and health centre. The rooms are furnished in traditional rustic Tuscan farm style.

Albergo Roma | 3 Star | Hotel

This small hotel is on Buonconvento's main street, so is ideally located for exploring on foot. Its comfortable bedrooms have been decorated in a clean, modern style but have also highlighted the building historical features. They have air conditioning and WiFi access.

Hotel Ghibellino | 3 Star | Hotel

Hotel Ghibellino is a modern 23 room three-star hotel in the centre of Buonconvento. It has an excellent reputation and the comfortable air-conditioned rooms are a relaxing haven.

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

Today starts with a short transfer to the well-preserved medieval fortified farm at Grancia di Cuna. It’s on the site of what was once a 12th century hospice and hospital for pilgrims on the Via Francigena. It’s worth taking the time to explore this historic site before beginning the walk to the UNESCO listed city of Siena.

Alternatively, it’s possible to take a transfer today to Colle di Malamerenda, which is closer to Siena. It’s an easier walking option, which is both shorter and less hilly and will allow more time to explore Siena on arrival.

Walk through a landscape of rolling hills and small hamlets as the unmistakable sight of Siena appears in the distance. Walk past vineyards and olive groves along the way. Finishing at the main medieval gate to the city, the Porta Romana, makes for a fantastic photo opportunity. A great end to a great tour!

Shorter walk from Colle di Malamerenda: 9kms/6mi Ascent/Descent: 134m/113m

Walk from Grancia di Cuna: 16kms/10mi Ascent/Descent: 234m/113m

Instead, there’s the option to arrange a private transfer today or grab a taxi (additional charges apply) to go directly to Siena and skip the walk, in favour of spending more time exploring this iconic city.

If time allows, we recommend adding an additional night in Siena, as this is an ideal location to relax in a café beside the main square or to explore the winding streets at a leisurely pace after completing this walking trip.

Overnight Siena

Accommodations

A sample of our typical carefully chosen accommodation in this location. Where you stay will vary depending on availability, but will be a similar standard.

Hotel Chiusarelli | 3 Star | Hotel

This 3-star hotel is situated in Siena town centre. Built around the year 1870 as a NeoClassical villa and completely restored in 2004, it keeps its original style as well as its beautiful frescoed rooms. In its 48 rooms you find every kind of a comfort: bathtubs or showers, linen, hairdryer, safe, air conditioning/ central heating, telephone, satellite TV, and bedrooms with a Wi-Fi Internet connection.

Hotel Santa Caterina | 3 Star | Hotel

This 18th-century residence was transformed into a hotel with all modern comforts. It’s ideally located for walkers, adjacent to Porta Romana gate into the historic city. It’s just a few minutes' walk from Piazza del Campo. The hotel prides itself on their attentive staff. The comfortable bedrooms are decorated in a traditional Tuscan style which is complimentary to the building’s historical features. They have air conditioning and WiFi access. There is a large panoramic garden where a bar service is available along with in the TV lounge. Upon request, a in bedroom massage service is available (additional charges apply and advance booking is recommended).

Hotel Athena | 4 Star | Hotel

Located inside Siena's historic walls, Hotel Athena offers an elegant Italian restaurant and a furnished terrace with views of the town and the surrounding valley. Internet is free. With air conditioning, rooms are spacious and elegantly furnished with warm colour schemes and tiled floors. Rooms on the upper floors offer beautiful views.

Day 8 Onward travel from Siena