• Tuscany Italy small group walking tour
  • Tuscany Italy small group walking tour
  • Tuscany Italy small group walking tour

Tuscany Walking Tour

Pilgrims Trail | Small group tours Italy

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.

Watch our tour video

Tuscany 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
  • As we walk, the Tuscan countryside begins to reveal countless interesting sights, 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 - on this Tuscany walk you work up an appetite and we restore your energy Tuscan-style; the delicious panforte or ricciarelli at a range of carefully selected restaurants

Tuscany walking tour- Pilgrims Trail

  • The Tuscany tour traverses the Tuscan countryside from Siena to Gambassi Terme - there are five days of walking
  • The walks are fully guided (no need to spend frustrating hours looking for the path!) and we organise for your luggage to be transported to our next destination each day
  • This walking tour is a balance between the more active side – the walks – along with enjoying the Italian cuisine, and visiting a range of interesting places
  • We stay in a range of characteristic Tuscan accommodation, including a farmhouse established in the 12th century, and a hotel based in a medieval palazzo in San Gimignano
  • Small Group Tours - maximum 14 people
  • This is the Tuscany trip that you’d design for yourself. We are Italy... with pleasure
  • Our 7 day Tuscany tour starts in Siena and finishes in Florence

Sicily Italy small group tour

What our customers say about Italy With Pleasure

“Everything was perfect! They packaged the hotel, all meals, daily tours to a variety of very special and interesting sites, and handled all of the myriad of details seamlessly. The agency is very customer-service focused and was a pleasure to work with. I highly recommend this tour company. Italy With Pleasure gets 5 stars!”

“I am widely travelled and have never been on a tour before so went with some trepidation.It was the absolute highlight of my travels in Italy and definitely the best food I had the whole time. I cannot recommend Italy with Pleasure more highly don't even think about it just book with them you will not be disappointed I am sure.”

“Our time travelling with ‘Italy with Pleasure’ was our best experience. Believe all that they say in their brochure... family run, hands on and very professional. Their standards are high and they are very responsive to everyone’s needs. They source excellent restaurants... way beyond our experiences with other companies we travelled with. We highly recommend this company, have mentioned it to friends and fellow travellers”

“The itinerary was well organized and done at a comfortable pace: touring in the morning followed by mouth-watering lunch featuring the specialties of the area as well as fine wines of the area. All of the restaurants were excellent as was the food. It was a wonderful week and I will have many fond memories of my stay. This tour is a gem and I highly recommend it!”

“The tour group was quite small, 8 people all delightful. We were driven to some very interesting towns and other sites, where guides introduced us to the art and history….The tour was full but not too intense so we felt we had enough time to enjoyed the excellent food and wine which were highlights of the tour for us. I wholeheartedly recommend this tour.”

“The places that we visited were fascinating and very unique, and the food and wine was delectable. I didn't know what to expect of the trip, but it more than fulfilled any hopes that I had for a great week. Everything was well organised and the atmosphere was friendly and relaxed. I can thoroughly recommend the tour.”

See these and other reviews on TripAdvisor


We have an interesting combination of accommodation as we move through the Tuscan countryside.

Starting in Siena we stay at the Hotel Duomo, very central with all the attractions of this wonderful city easily accessible on foot.

For our first night on the trail we stay at Borgo Galliano, a rural lodge, beautifully presented in amongst fields and oak trees.

Moving on, we stay at the Tenuta Mensanello, a collection of old stone buildings set amongst a working farm. You can enjoy their homegrown food and wine at their excellent restaurant.

Our next stop is the town of San Gimignano, where we stay at the Hotel Antico Pozzo. You’ll love the Tuscan style of this establishment, set right in the heart of San Gimignano.

For our final night we stay at the Tenuta Sant’Ilario, a boutique hotel where you can celebrate the finish of your walk with a swim, followed by some top cuisine in their restaurant.

Borgo Galliano amd Antico Pozzo Tuscany Italy

Day 1:  Buongiorno Siena!

We meet in Siena in the afternoon, in our hotel that is right in amongst the historic centre of Siena.

Before any thoughts of walking we head to a café for some of Siena’s renowned foods such as ricciarelli and cantucci.

For those that haven’t seen Siena, we take a walk together to the cathedral, where you discover some interesting quirks of its construction and history. And looking around our part 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.

In the evening we walk through the centre of Siena – through the Piazza del Campo, tonight full of people enjoying their evening aperitivo rather than racing horses.

We have dinner together in a trattoria 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.


This walk is fully guided
Total distance: 11 miles / 18 km

Meals included: Dinner
Accommodation: Hotel Duomo

Day 2: Into the Tuscan Countryside

Today we set off on the first section of our walk (and we start to appreciate that our luggage is being transported for us; we only need to carry what we need for the day).

As we make our way out of Siena we come across many examples of how this city lived and fought in the centuries past. History is all around us, we explain to you what you are seeing and the significance of Siena to the region.

The trail that we are following this week, the Via Francigena passes right through Siena.

We reach the outskirts and the verdant countryside that will be our environs for the week. We follow the route and soon reach the first ‘strada bianca’ (‘white road’). These are the more peaceful rural trails that we will follow for the next few days, 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.

We stop for lunch at a small rustic eatery right on the trail – here you’ll get your first feeling for the Tuscan hospitality.

As you adjust to the pace and rhythm of the walk you start to pick up on the smaller details and the more subtle changes through the day. The way people live here, with their family olive groves and well tended gardens. The small scale farms that are the foundation of this region. The beauty of the Tuscan countryside. The 16th century castle Chiocciola that we pass today.

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

Mid afternoon we reach our accommodation for the night, Borgo Galliano. This is an ‘agriturismo’, a country lodge.

We take a break for a few hours to put our feet up and reenergise before meeting for dinner. We enjoy a meal in the restaurant of our lodge.


This walk is fully guided
Total distance: 11 miles / 18 km

Meals included: Dinner
Accommodation: Borgo Galliano

Day 3 - Monteriggioni to Colle di Val d’Elsa

Departing from Borgo Galliano (and wishing we could stay more than just one night!), a short walk 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 an hour or two for you enjoy being in Monteriggioni, time 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. Mid morning we exit the town walls at the Porta di Ponente gate - the route of the Via Francigena.

We walk for just long enough for you to work off your morning gelato before coming to 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.

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 this week. 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 stop in to look at some ancient Etruscan (and later Roman) baths at Caldone.

We reach the Tenuta di Mensanello, a boutique hotel based in a small hamlet. There’s time for a swim in their pool, a look around their gardens, before finding those rewards awaiting a weary pilgrim in the evening - they make their own wine and grow much of their own produce, this is farm to table at its best.


This walk is fully guided
Total distance: 9 miles / 15 km

Meals included: Breakfast, Lunch
Accommodation: Tenuta di Mensanello

Day 4 - Colle di Val d’Elsa to San Gimignano

We set out from our destination today, continuing north towards the town of San Gimignano. En route 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.

Today you meet the locals for lunch, in a small inn. Soon we start to see the medieval towers of San Gimignano, erected by the noble families in a bid to out do each other.

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.

We reach our hotel for the next two nights, the Hotel Antico Pozzo. This hotel is right in the historic centre of town, nestled in the evocative lanes. From here you can wander into the piazza and watch the world go by.


This walk is fully guided
Total distance: 12 miles / 20 km

Meals included: Breakfast, Lunch
Accommodation: Hotel Antico Pozzo, San Gimignano


For today’s walk we do an excursion from San Gimignano, returning in the afternoon to our base. Our walk today, a diversion from the Via Francigena, is through the renowned vineyard area of San Gimignano.

This is a scenic walk following a route that gets us up close to the vines that form such a key element of the Tuscan landscape. The key wine made here is vernaccia, a white wine with a long history – it was first recorded here in 1276. It still tastes good in the present too, we enjoy some of the local product over lunch.

This excursion returns to our departure point in San Gimignano.

As we stay another night here in San Gimignano, anyone who wishes to rest their legs can skip the walk - simply stay put and soak up the atmosphere of the town. There is plenty to see here and your more relaxed day will allow you to enjoy our next walk tomorrow. Or simply find a good spot in the piazza with a glass of local vernaccia and watch the world go by.


This walk is fully guided
Total distance: 10 miles / 15 km

Meals included: Breakfast, Lunch
Accommodation: Hotel Antico Pozzo, San Gimignano

Day 6: Our final destination, Gambassi Terme

Today you walk along one of the more scenic areas in Tuscany, and it is our last leg of our journey. We make our way thought the classic Tuscan countryside, stopping when there are interesting sights to see, such as the Sanctuary at Pancole with its fascinating back story.

Walking through this countryside you can see how some aspects of life here follow the seasonal cycles of planting and harvest, as they have done for many generations.

We reach our destination – the boutique hotel Tenuta di Sant’ Ilaria, which is actually on the intersection with another ancient route, the Salt Road.

Our accommodation is entwined with this history, the oldest part of the complex where we stay, was built in the 12th century.


This walk is fully guided
Total distance: 8.5 miles / 14 km

Meals included: Breakfast, Lunch, Dinner
Accommodation: Tenuta Sant’ Ilario

Day 7: Arrivederci Tuscany

Today is our last day, we travel back to Florence and bid you “buon viaggio”. The tour finishes in Florence at 11:30 a.m.

Meals included: Breakfast

Siena Tuscany small group walking tour

Tuscany small group walking tour

Monteriggioni Tuscany small group walking tour

Monteriggioni Tuscany small group walking tour

San Gimignano Tuscany small group walking tour

Castelvecchio Forest Tuscany small group walking tour
Gambassi Terme Tuscany small group walking tour

Tuscany Pilgrims Trail Walking Tour Dates:

This tour is run on request for groups of six or more.

Tour Price: €2500

* Prices listed are based on twin share
* Single supplements of €300 for solo travellers

Tour Price Includes:

  • All accommodation
  • Meals as listed in the itinerary: breakfast every morning, plus a main meal each day
  • All costs/entry fees for activities listed in the itinerary
  • All transport during the tour. Travel is in our van/minibus with a professional driver
  • Daily luggage transfers
  • 'Italy With Pleasure' provides a tour manager for the duration of the trip

Tuscany Map

Sicily small group tour map

Sicily small group tour