Tuscany Walking Tour 2026

We meet in Florence and depart for our accommodation, the Tenuta di Mensanello.

This is a historic farm estate, now operating as a boutique hotel. By staying in here you will be directly experiencing a working agricultural property.

Set amongst olive groves and vineyards, the property developed from the 11th century onwards. Around the grounds you will see numerous aspects of times gone by, giving an insight into the lifestyle here in centuries past – you are immersed in history. For this week, you live amongst it.

But we don’t forget the needs of the present! The Tenuta di Mensanello offers all you would expect during your time here, such as wifi, air conditioned rooms, and a swimming pool.

We spend some time in the afternoon exploring the property – their vineyard, their crops and farming activities, the forested areas. We delve into their production philosophies, which are focused on compatibility with their land and the use of heritage varieties.

In the evening we have dinner together in their restaurant right here on the estate. This is our first introduction to the Tuscan cuisine, much of which is grown on the farm right outside our door. This is farm to table at its best. During the week we will continue our exploration of Tuscan cuisine, with a progressive discovery of the local cuisine.

Meals: Dinner

Today we set off on our first walk. The trail that we are following today is part of the Via Francigena pilgrimage route. The trail is known as a ‘strada bianca’ (‘white road’). These are peaceful rural trails, small white gravel roads and paths that are typical of the Via Francigena in Tuscany. Many of these paths have been upgraded in recent years making for an excellent walking route.

We start at the 12th century Abbey of Santa Maria a Coneo. Through the morning we find our rhythm as a walking group – we have planned the days to include time to stop and look at points of interest along the way, our days aren’t a race to the finish but rather a gradual exploration of the territory.

This is the aim of our tour – to give you time to appreciate you environment, to fully explore the cuisine, as well as seeing the numerous historic sites every day on our trail.

Soon we start to see the medieval towers of San Gimignano, erected by the noble families in a bid to out do each other.

As we reach San Gimignano we first have lunch together in one of our favourite trattorias, before going on to discover the town.

San Gimignano is one of Italy’s most well-preserved medieval towns. Perched on a hilltop with numerous medieval towers, it is a commanding presence dominating the patchwork of olives and vineyards in the valley below. San Gimignano’s narrow streets boast many craftsmens’ workshops. And there’s a particularly good gelateria in the piazza.

You have free time to explore the town independently, after which we meet our driver to return to our accommodation.

WALKING DETAILS:

• The walk is fully guided.
• Total Distance: 6.8 miles / 11 km

Meals: Breakfast, Lunch

Today we head into a river valley nearby. The river skirts alongside the town of Colle di Val d’Elsa. After an initial section of road we start along a path beside the river. We come across a waterfall called the Cascata del Diborrato. There are various swimming holes along the river, well used by the locals during the summer. We reach a stone river crossing, and enjoy the easy shaded route.

We stop in at the town of Colle di Val d’Elsa for lunch, before returning back to our accommodation in Mensanello.

In the afternoon, we have some free time at the Tenuta di Mensanello.

For the evening we travel to the nearby town of Volterra. As well as the Etruscan and Roman features here, this is a classic Tuscan hill town.

After we see some of the town together, you have time to look around yourself – wandering cobblestone lanes inside the ancient town walls, finding that perfect trattoria for dinner, or just an aperol spritz on the piazza if you prefer.

WALKING DETAILS:

• The walk is fully guided.
• Total Distance: 3.7 miles / 6 km

Meals: Breakfast, Lunch

Today’s walk is through classic Tuscan countryside, along lanes lined with cypress trees. Today’s walk is not physically demanding, after an easy stroll through forested land and vineyards we reach a winery where we taste their wines.

Chianti is one of the best known type of Italian wine – and has the longest history, the official wine zone was created in 1716. We taste their flagship Chianti red wine, but they also offer white and rose wines so there’s something for everyone.

Continuing on, another short walk takes us to a monastery that was established in the year 890 AD. Our lunch is a casual affair, sharing platters of local delicacies while sitting on a terrace overlooking their vineyard.

We then drive to the nearby town of Castellina in Chianti, which features a small piazza alongside the 15th century castle. We enjoy the village atmosphere, and make time for a gelato or a coffee

Next we view an Etruscan burial site nearby, the Tomb of Montecalvario. Etruscans were one of the early populations in Tuscany, in pre-Roman times. This tomb has four chambers partially underground in a burial mound, and was constructed in the 6th century BC.

WALKING DETAILS:

• The walk is fully guided.
• Total Distance: 3.7 miles / 6 km

Meals: Breakfast, Lunch

Today is an urban walking tour, in contrast to the more rural routes that we have followed so far. We spend the day exploring the town of Siena. On a guided visit we look around various parts of town you’ll see how loyal the locals are to their zone – the area that they represent in the palio, the bareback horse race around the central Piazza del Campo. We continue on to see the cathedral, where you discover some interesting quirks of its construction and history. Once the capital of a republic, and arch rival of Florence, Siena has a rich and varied history.

We also leave the afternoon for you to see Siena independently. Most people head to a café for some of Siena’s renowned biscuits such as ricciarelli and cantucci. A great idea is to visit one of the historic cafes of the town centre, such as Caffe Poliziano, which started in the 1800s.

Meals: Breakfast

Today we are heading south, again on the Via Francigena. We leave on foot from our hotel. We follow the trail in the afternoon over the gently rolling hills. The vineyards we pass through in this part of Tuscany are part of the Chianti wine zone, and they promise us a welcome reward at the end of the day. The route we are on was documented by Sigeric, the Archbishop of Canterbury, in the year 990. Sigeric was travelling to Rome to meet the pope, and his travels became the Via Francigena.

We reach our lunch stop, which is a restaurant contained within a 12th century monastery complex, the Monastery of San Salvatore. Originally this would house pilgrims en route to Rome, so we dine in a courtyard that has seen many centuries of monks walk its paving stones. A short walk after lunch takes us to the town of Monteriggioni. The small piazza and old stone buildings are simply charming, this village has a medieval feel. We allow time for you enjoy being in Monteriggioni, and to look around the central village. Monteriggioni is a rare example of a town still contained within the original 3th century walls, just as it was centuries ago. You can walk along the top of the town walls, or simply relax in the piazza with a coffee or gelato. You’ll notice numerous references to the Via Francigena here as Monteriggioni is a well known stop on the route.

WALKING DETAILS:

• The walk is fully guided.
• Total Distance: 7.5 miles / 12 km

Meals: Breakfast, Lunch

We provide transport to Florence so you are ready for your onward travel.