Italy With Pleasure

Tuscany Walking Tour

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7 Day Tour
14 people max
All inclusive
Min Age : Refundable deposits

Many of us have already visited well known Tuscan hotspots such as Florence or Pisa. But just as rewarding are the lesser known sights that we take you to on our Tuscany Tours – having lunch in a monastery founded 1000 years ago, walking through the evocative Tuscan countryside and coming across ancient Roman baths.

Being on foot, we have plenty of time to fully appreciate the Tuscan countryside on our Tuscany Walking Tour. A glass of Chianti at the end of the day sourced from the vineyard right outside your door is also not to be missed.

Our tours are a balance between being informative (examples of the culture and lifestyle, historical details) as well as having everything that makes for an enjoyable trip (long lunches in good restaurants, a relaxed pace). We plan the itinerary in the way that you would plan to travel yourself, or with a group of friends.  


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.

We spend some time in the afternoon exploring the property – their vineyard, their crops  and farming activities, the forested areas. This is farm to table at its best.

In the evening we have dinner together where we enjoy the local cuisine – this week,  while primarily about walking – is also a chance for us to enjoy 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. The trail is 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.

Through the morning we find our rhythm as a walking group – we have planned the days to include time to stop and look at anything of interest along the way, our days aren’t a race to the finish but rather a gradual exploration of the territory.

En route to San Gimignano we find a number of interesting features, such as the Romanesque church of Santa Maria a Coneo. We also have a special chance to see the site of an Etruscan necropolis (cemetery), the population that lived in Tuscany before the Romans.

This is the aim of our tour – to give you time to appreciate you environment, to fully eplore 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. We first stop on for a lunch of Tuscan classic dishes, 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. After some time to explore the town, we meet our driver to return to our accommodation.

WALKING DETAILS: The walk is fully guided.

Total Distance: 6 miles / 10 km

Meals: Breakfast, Lunch



Today’s walk is through classic Tuscan countryside, with vines and lanes of cypress trees. After an easy stroll through forested land and vineyards, we reach a winery where we taste their wines, along with a light lunch. This gives us a chance to see how this working agricultural enterprise operates, and the care for the land that they demonstrate. Continuing on, another short walk takes us to an 11th century monastery.

We then drive to a nearby town 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: 5 miles / 8 km

Meals: Breakfast, Light 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. Today’s walk is intentionally not challenging, so everyone can recharge. 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. If you want more than just relaxing by the pool, you can choose to do an olive oil tasting or some cooking with the chef.

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

Meals: Breakfast



Today is an easier day, to give your legs a rest. We still walk, but in an urban environment 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. 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 caffes 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 just as they did for the pilgrim Sigeric in the year 990, when he documented the route that we follow today. Sigeric was the Archbishop of Canterbury, travelling to Rome to meet the pope. His notes from that journey are an early reference to this pilgrim’s trail. We reach our lunch stop. The restaurant is contained within a 12th century monastery complex, the Monastery of San Salvatore. Originally this would house pilgrims en route to Rome. 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. This village has a medieval feel, and is still entirely contained within the 13th century walls, just as it was centuries ago when Siena and Florence were rival city states. The small piazza and old stone buildings is simply charming. 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 medieval walls. You’ll notice numerous references to the Via Francigena here as Monteriggioni is a well known stop on the route – in fact it is unmissable.

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.

Tuscany Walking Tour Dates 2025:
Cost and Inclusions


* Price is denominated in Euros. Price listed is based on twin share
* Single supplement of €300 for solo travellers



We stay at the Tenuta di Mensanello, a collection of historic stone buildings that developed initially around a chapel in the 11th century, gradually expanding over the centuries.

Today this is run as a boutique hotel, with the agricultural activities still carrying on too. The farm and accommodation are family run. They produce a range of crops and olive oil. You can enjoy their homegrown food at their excellent restaurant.

And a glass of Chianti at the end of the day sourced from the vineyard right outside your door is also not to be missed.


P B Google Reviews Logo

The tour was terrific as was the hotel accommodation, and Andy was the best! It was well organized and we didn’t skip a beat. That last night at the farmhouse was memorable and the perfect send-off. The tour guides in each of the cities we visited were well informed and did a great job explaining what we were seeing.
I highly recommended Italy With Pleasure to people I know that might be interested in travel to Italy. The small group size, and in our tour, Andy, is what makes it happen.

C L Google Reviews Logo

We had a fantastic time on this trip. Ricardo was wonderful and we all really enjoyed his company and knowledge of the area. Another fantastic Italy with Pleasure trip. I love this company for providing a small, private tour atmosphere, with attention to detail on food, logistics and educational site visits. You guys are amazing. Until next time.... thanks so much.

M G Google Reviews Logo

We had a most wonderful time and a most wonderful tour guide, Mark. Mark was personable, knowledgeable and accommodating. We would love him as our guide on another tour. Each town we visited had another guide specific to the that history and culture. Everything was beautifully planned out and well executed. Our room was beautiful, our view was breathtaking, we could not have asked for a more memorable trip!!

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