They Saw Tuscany on Foot: The Ultimate Walking Tour

When I daydream of Italy it’s of images of intimate little towns with narrow streets, patrons spilling onto the pavement restaurants while they enjoy slow-paced lunching, fresh produce, cheese, wine, rolling Tuscan landscapes and iconic cities. Photographer Daniela Zondagh spent a European summer exploring Italy in a unique way – by foot. She shares her images and experiences with us – a real Italian immersion and a great way to really experience Tuscany.  

The Trip

In the European summer we decided to explore Italy by foot. 

After spending a couple of days in Rome we headed to Chiusi by train. Here we were picked up by Beppe who worked for Viadelsole, the company that organises self-guided walks through Tuscany. He drove us to the beautiful little town of Montepulciano where we spent our first night and prepared to start our 6 day walk which would take us from one beautiful hillside town to the next. 

Each morning a representative from Viadelsole came to collect our main luggage and we just need to carry water and a little snack with us. But mostly the walks went through little towns and farms where we could buy fresh produce to have a little picnic lunch or snack before the last stretch. We walked between 12 – 17km per day through the rolling hills of Tuscany with direction and a map of where we needed to go. Routes were mostly on farm tracks through privately owned land – scenery you would never be able to see when just touring by rental car.

Accommodation & Food 

We stayed in all different types of accommodation – from small bed and breakfasts, luxury boutique hotels and we also spend two evenings at an Agriturismo on a farm.

Each little town had it’s own little unique restaurants that served meals made with fresh local produce – a foodie heaven! We didn’t book anything in advance but on arrival in each little town we asked the locals where they ate and we booked a table there. One thing I have learned from traveling is eat where the locals eat – these are always the best places.

The Itinerary 

Day 1 : 

Arrival in Montepulciano.

Day 2 : 

Took us from Montepulciano to Pienza. Pienza is a UNESCO World Heritage Site and only has a population of 2300. The town is renowned for the movie The English Patient which was largely filmed at the nearby Sant’ Anna Monastery and in some parts of the town. Pienza is also well known for the amazing parmesan cheese they produce. Foodie heaven.

Day 3 : 

Pienza to Bagno Vignono took us through picture perfect Tuscan landscape – green hills and cypress trees, stone farmhouses standing alone on hilltops. Bagno Vignoni is a unusual place with a hot spring spa built around a sometimes steaming city square. Ideal for revitalising in hot springs after a strenuous walk.

Day 4 : 

Bagno Vignoni to Montalcino – after walking to Sant Antimo Abbey a driver picked us up to take us to Montalcino. With a population of 5 000, Montalcino is a classic little hillside village – it’s appearance has not changed in the last 500 years. Famous for its Brunello wines.

Day 5 : 

Montalcino to Buonconvento. Walking through farmlands and wineries we reached our Agriturismo where we stayed for two evenings and explored the surrounds over the next couple of days.

Day 6 : 

Monte Oliveto Maggiore to Buonconvento. For a shorter route exploring the surrounds a shuttle came to collect us and drop us off at Monte Oliveto Maggiore – the house of the Olivetians, or white Benedictines – a congregation of monks founded in 1313 by Blessed Bernardo Tolomei in Siena.

Day 7 : 

The final day to Siena started with a shuttle to Crancia di Cuna and then a 16.5 km hike. Arriving in Siena was a sure highlight of our trip. We arrived two days before the world famous Palio Horse race that takes place in Siena on the 16th of August. Jockeys ride bareback in the Piazza del Compo. The vibe in the city was electric and they had started to set up in the Piazza del Campo, the shell-shaped square in the heart of the town at the Palazzo Pubblico with the Torre del Mangia towering high above the square.

Another beautiful scene in Siena is the Siena Cathedral – a medieval church designed and completed between 1215 – 1263 which is absolutely breathtaking to see. We left Siena the day before the Palio race but will certainly to be back there one day for the race.


Don’t carry to much with you daily. Camera, water, some money and something to snack on. There are places where you can buy more water – just make sure you follow the route as per instructions. A good backpack, hat, sun screen and walking shoes are essential. If for some reason you can’t walk on a day take a lift with your bag to the next little town but be warned that you do miss out on some beautiful scenery along the road. Each day is different and the landscapes and beautiful little towns you walk through are all gorgeous. Because you are walking off the beaten track not everyone speaks English but everyone was always very helpful.