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 landscapes 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.
Tuscany Walking Tour Highlights
- Walk along the pilgrims trail called the Via Francigena, a route leading from Canterbury in England to Rome - developed in the 10th century
- Spend time in San Gimignano, Siena, and our favourite, Monteriggioni – a picturesque village still contained within the medieval walls
- A series of hiking trails in Tuscany that take you through areas where you are immersed in the untouched and traditional areas of Tuscany. Here the many centuries of history are revealed to you as we pass through at a pace allowing you to appreciate the smaller details, whether it be an Etruscan tomb, the abundant wild flowers, or deer emerging at dusk
- Enjoy a range of local Italian food along the way - walking in Tuscany is a great way to work up an appetite and we restore your energy Tuscan-style; the delicious panforte or ricciarelli, and a range of carefully selected restaurants
Tuscany Walking Tour Itinerary
DAY 1: BUONGIORNO TUSCANY
We meet in the city of 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.
Mark from Australia writes: “I have to say that the Tour certainly exceeded my expectations. Every aspect, the accommodation, meals, scheduling, and in particular the leadership from our guide Riccardo was 10 out of 10.The many guided walks I have done in other countries were also very well organised, but yours was the best.” (from Google Reviews)
Meals: Dinner
DAY 2: SAN GIMIGNANO
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 tracks 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 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, amongst the rolling hills, 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 artisan workshops. And there’s a particularly good gelateria in the piazza. While busy in the summer months, our visit is off peak and a great time to be here.
You have free time to explore the town independently, after which we meet our driver to return to our accommodation.
Our small group tour advantage: Your tour leader is your ‘safety net’. Many people appreciate having their tour leader to be able to turn to, whether it be for help getting something from a pharmacy / drugstore, or simply where to find the best gelato! While you are far from home, you can count on your tour leader and their support team for anything that you need to deal with.
WALKING DETAILS: The walk is fully guided.
Total Distance: 5.6 miles / 9 km
Meals: Breakfast, Lunch
DAY 3: WALKS AND WINE
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 olive groves 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.
At this family run estate we taste their flagship Chianti wines, while sitting on a terrace overlooking their vineyard.
Continuing on, another walk takes us to a monastery that was established in the year 890 AD. In the medieval hamlet nearby we have lunch.
We then drive to the nearby town of Castellina in Chianti, which features a small piazza alongside the 15th century castle. This is one of the classic Chianti destinations, where you can wander along the main street amongst interesting shops and cafes. 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. This visit fills in some of the history of Tuscany.
WALKING DETAILS: The walk is fully guided.
Total Distance: 3.7 miles / 6 km
Lisa from USA writes: “I had the good fortune to take Italy With Pleasure’s Walking Tour of Tuscany this past May. Each day, our adventure and locations got better and better! So carefully crafted from the paths chosen, to the towns/cities visited and the restaurants selected. Riccardo, our tour guide was fabulous…a great friendly spirit with a considerable breadth of knowledge. He is so welcoming and does a great job of making his guests feel special. I have recommended Italy With Pleasure to many seasoned travelers who are looking for a unique experience. Thank you, Italy With Pleasure” (from Google Reviews)
Meals: Breakfast, Lunch
DAY 4: RIVER ELSA WALK - VOLTERRA
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 the woodland trails that we follow 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.
Our small group tour advantage: We give the tours a personal feel. With a maximum of 14 in our groups, the feel of our tours is like travelling with a group of friends. We make our tour the style that you want, for example our focus on good restaurants – the sort of places you’d choose yourself. And not cramming too much into one day. All this gives your time with us a less commercial feel and ensures that we maintain a relaxed atmosphere.
WALKING DETAILS: The walk is fully guided.
Total Distance: 6.2 miles / 10 km
Meals: Breakfast
DAY 5: SIENA
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.
Neil from New Zealand writes: “You must use these guys if you are doing tours in the regions of Italy they operate in. They do small group tours and are simply the best we have experienced throughout Europe.” (from Google Reviews)
DAY 6: MONTERIGGIONI
Today we are heading south for the last of our hikes in Tuscany, again on the Via Francigena. We leave on foot from our hotel. We follow the dirt roads 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, today’s marked path. 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.
After lunch we visit the town of Monteriggioni. The small piazza and old stone buildings are simply charming, this village has a wonderfully unspoilt 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 do a circular walk along the top of the town walls to enjoy the fantastic views, 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 – in fact it is unmissable.
Our small group tour advantage: Our local insights help you to maximise your time. When you are in a country or region only for a week or two you want to make the most of your time. On our tours, we give you the local insights, the understanding of what you are seeing. Without this, you might recognise that a particular feature or building seems interesting, but not ever know the full story behind it. Guidebooks will detail the main monuments or museums but tend to be quite limited when you start to see the smaller (and often more interesting) sights.
WALKING DETAILS: The walk is fully guided.
Total Distance: 5.6 miles / 9 km
Meals: Breakfast, Lunch
DAY 7: DEPARTURE
We provide transport to Florence so you are ready for your onward travel.
Tuscany Walking Tour Cost and Inclusions
TOUR PRICE: €2500
Price is denominated in Euros. Price listed is based on twin share/double occupancy
Single supplement of €300 for solo travellers
- All accommodation is included
- Meals as listed in the itinerary: breakfast every morning, plus a main meal each day including wine
- All costs/entry fees for activities listed in the itinerary are included
- All transport during the tour is included. Travel is in our minibus with a professional driver
- 'Italy With Pleasure' provides a tour leader who will be with you for the duration of the tour, on hand to provide any support that you need
Tuscany Walking Tour Accommodation
We stay at the Tenuta di Mensanello, a collection of stone buildings that developed initially around a chapel in the 11th century, gradually expanding over the centuries.
Today this is run as a ‘agriturismo’ farmstay accommodation, 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.
Tour Reviews
P B 
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.
Click here to see full review
C L
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.
Click here to see full review
M G
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!!
Click here to see full review
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