Tuscany walking tours. Managed and guided by experienced local professionals



Dates of tour in 2017 Available places
May 14-21 Full
May 23-30 Full
June 6-13 Full
June 20-27 Full
Sept 9-16 Full
Sept 16-23 Full
Sept 23-30 Full
Oct 7-14 Full
Oct 18-25 Full
Oct 29 – Nov 5  Come see colors and taste the best food in Tuscany!

This tour has been designed with a background of 15 years of guided walking tours in Tuscany. Explore the medieval towns: Siena, San Gimignano, Montalcino, Pienza, Vald’Orcia. Taste oil, wine and vegetables at family-run farms. Walk the many paths that connect the villages with memorable panoramas. Meet other people that love to walk slowly and learn about Italian culture.

What makes us special

  • GUARANTEED DEPARTURE! Even if we have just you on tour we are committed to operate the tour. Book soon with us and book your flight to Italy!
  • We are LOCALS. We have been born and raised in Tuscany. We know how to stay away from the crazy crowds. We know the little secrets that will make your stay unforgettable (a couple of examples: 1) San Gimignano, the town with 14 towers, needs to be visited before 10.30am; later that that it will be crowded with tourists. 2) Pici thick spaghetti handmade pasta is available everywhere in this region but only few restaurants provide the true hand-made…and we know where this is 🙂
  • It is a SMALL GROUP tour (group is not larger than 18)
  • RELAXED PACE: 5 to 7 miles (3-4 hours average) walks on each day. WALK RATING: 2+ on a base of 1=easy to 5=strenuous
  • LOCAL GUIDES: 1 walking guide for groups of 9 guests or smaller. Groups of 10 guests or larger will be guided by 2 guides
  • EVERY DAY A SPECIAL ACTIVITY: Opera, truffle hunting, Olive oil farm visit, family-run farms experience and a lot more.
  • IT’S A RESPONSIBLE WAY OF TRAVELING: We employ all local small businesses; small farms, local guides, family run hotels and restaurants. If you buy our tours you will give back a lot to the area, contributing to mantain the economy of this region. Thanks a lot for doing this!


  • 7 night stay at small hotels (3 and 4 stars). All the hotels are conveniently located in the town historical centers. Book early and we will try to accommodate you in a room with a view.
  • All breakfasts. 6 lunches. 5 dinners.
  • Transportation along the tour
  • 1 local guide for groups smaller than 10. Groups larger than 10 people will be guided by 2 local guides
  • Entrance tickets for all the special events
  • One Chianti and two Brunello winery visits and tastings: you will talk to the owners!
  • Learn about cheese making at a small farmhouse in Pienza followed by a nice lunch based on cheese
  • One short pasta making cooking class with Carmela and Samanta. A lot of fun!
  • Opera singing night special show
  • Tourist tax (it’s a payment made to the local authority of the area in which a tourist buys accommodation)
  • All taxes

  • Tour beginning: Siena at 5.00pm of day 1. You can comfortably check-in at your hotel starting at 2pm. Very convenient if you are travelling from other cities like Florence or Rome.
  • Tour end: 10am of day 8 by the train station of Chiusi-Chianciano Terme on the main railway to Florence (North) and Rome (South)
  • Day 1 – Meeting in Siena (Night at hotel in Siena)
    We will meet the group at hotel’s lobby. A brief informal introduction followed by an aperi/cena (aperitive and dinner together) in the main square of Siena. You might want to try the aperol-spritz that drives all the Italians crazy. Or maybe a Prosecco. A light dinner based on cheese, cold cuts, crostini (breads with spreads) will be served along with your aperitivo. At 9.15pm we are all invited for an Opera singing show (about one hour long)
  • Day 2 – Chianti walk, winery experience and visit of Siena (Night at hotel in Siena)
    Today we set off to Chianti, one of the most well known area for wines. The walk will take us through olive groves and vineyards. We then stop at a family run organic Chianti maker (Casina di Cornia: two brothers and their dad) that will explain to us how they make their wine so special. Lunch will follow by a nice restaurant on a pond side. A short drive will take us back to Siena for some rest before that we join a art guide to explore the city. Dinner tonight is on your own.
  • Day 3 – San Gimignano and pasta cooking class (Night at hotel in Siena)
    Today we will explore the area of San Gimignano. The town still has 14 high medieval towers.
    The 7 miles walk in the countryside, with some elevation gain, goes through olive groves and vineyards of Vernaccia di Sangimginano, the most famous white wine in Tuscany.
    We will finish our morning walk at a vegetable garden farmhouse run by the Ganozzi family. They will serve us lunch based only on their production. It will be so delightful to sneak-in into their grounds and see which vegetables they are producing.
    A short transfer back to Siena. After a good rest Carmela and Samanta, two sisters, will host us for a short pasta hands-on cooking class followed by dinner.
  • Day 4 – Montalcino and Brunello Casato Prime Donne winery experience (Night at hotel in Montalcino) 
    It’s transfer day! We drive for 40 minutes to Montalcino. We will spend the next two nights in this medieval town. After a short visit of Montalcino we venture on a beautiful panoramic 5 miles walk to the winery Casato Prime Donne. This winery is run only by women. These brave ladies will host us for a winery visit and for lunch too. After lunch we drive back to Montalcino and explore more of this cute town, perched on top of the hill. After some rest we reconvene and we walk to a trattoria that serves local specialties.
  • Day 5 – Montalcino and  Brunello Il Cocco winery experience (Night at hotel in Montalcino)
    This morning we start directly from the hotel. The path takes you through thick natural forest and panoramic views over the Monte Amiata (an extinct volcano). After 6 miles of walk we will reach the “Il Cocco”, farm run by 3 young brothers (Giacomo, Stefano e Ettore). Giacomo, the elder brother, will capture our attention with his deep knowledge about wine making. It will be so nice to walk through his vineyard with a glass of Brunello. Lunch at the farm small restaurant will follow. After lunch we will continue the walk for 3 more miles with the goal of Sant’Antimo church, founded by benedictine monks. We then drive back to our hotel in Montalcino. Tonight dinner is on your own in Montalcino with many possibilities.
  • Day 6 – Pienza and San Quirico. Visit of an olive oil mill  (Night at hotel in Pienza) 
    A 30 minutes transfer will take us today to Pienza; we will be in Pienza for the next two nights. Pienza is a nice combination of medieval and renaissance buildings. Pienza is a terrace that overlooks the beautiful and green Vald’Orcia. We start our walk from here and after 6 miles we will reach San Quirico d’Orcia, a hidden and less frequented town. The family Simonelli owns an olive mill from generations. we will visit the mill with the owner, learn about the olive oil making and taste the olive oil. In San Quirico the restaurant Osenna makes hand made pici pasta. You don’t want to miss this pasta with fresh truffle sauce. After lunch we explore San Quirico and it’s beautiful gardens. A short drive back to Pienza will take us back to the hotel. Dinner tonight is at the hotel’s restaurant.
  • Day 7 – Monticchiello and cheese making farm  (Night at hotel in Pienza) 
    After a generous breakfast based on eggs and cappuccino we start our walk directly from the hotel. We pass through wheat fields. After a couple of hours walking we will reach Il Casale cheese farm, nearby Monticchiello. Sandra will show us how they make pecorino sheep cheese: from the 10 day aged cheese to 20 months old cheese. The sheep are raised in this farm from generations. A nice lunch based on pasta, pecorino (of course!) and local wine will follow. You can decide to be driven back to the hotel or join your guide on walk back to the hotel. Tonight the farewell dinner is at a small trattoria where the locals go. Porcini mushrooms (according to the season) or more pici pasta and fresh made dessert will leave a sweet taste and memory.
  • Day 8 – Departure day
    At 9.00am a drive of 45 minutes will take you to the train station of Chiusi-Chianciano Terme. This train station is conveniently located on the main railway and in about two hours by train you will arrive to Florence (North) or Rome (South).

The Only Way to Experience the Hilltop Towns of Tuscany! (Joe and Mila, USA)
My husband and I spent 7 days in September walking the Tuscan Hills with Gianni and Rudy. Truly one of our best and most memorable travel experiences.
If you want to see a beautiful country from off the beaten path with a guide that shares his vast knowledge of the food, wine, history, and geology of the Tuscan Hills – go on this trip! Gianni’s love of his country is so strong – that you cannot help leaving this country sharing his love. His choice of lodging, restaurants, and walking trails were just perfect.
As I read my journal from our trip almost 3 months ago it brings a smile to my face as I relive those treasured moments of hiking beautiful vineyard hillsides, making pasta at a local restaurant, listening to arias from well known Italian operas, drinking glorious wines with local wine makers, eating fabulous foods, learning about making cheese, doing yoga in a beautiful vineyard and listening to Gianni play his flute. I could go on, however my strong advice is to experience this yourself – it is truly the only way to visit the hills of Tuscany and its beautiful historic towns. Gianni is not only a true professional but also a charismatic, intelligent man who has an incredible understanding of the culture of his country. Gianni’s organizational skills and ability to relate to all his guests was a large part in making this trip so memorable and enjoyable.

Under the Tuscan Sun (and a big black cloud but only once (Linda M., Canada)
I have just returned from 8 fabulous days with Walk About Tuscany hosted by Gianni and Rudy and helped by their hard working transportation crew who ensured we were picked up on time, we travelled safely and no luggage was lost. Congrats to them.
I was in a group of 16, coming from many parts of the world and put together by chance. We were treated to a Tuscan experience which will, for me, remain a memory for years to come. We saw everything; from the hill top towns to the wheat fields, from the vineyards to the olive groves, from the churches to the abbeys to the quaint shops and cobblestone streets and each day was a different adventure. We got up close and personal with the Tuscan people, sharing their food, their wines, and learning about their way of life.
This was also a walking tour and, boy, did we walk (so sturdy shoes are recommended). It is estimated we covered close to 100 miles, some easy trails, some more challenging climbs. If anyone in the group fell behind or needed time to catch a breath, there was always someone available for company. We were never rushed but there were times we had to be gently reminded that we have a date for lunch or for a wine tasting and we should try not to keep our hosts waiting.
We learned so much during each walk; Gianni and Rudy switching back and forth to cover the plantlife and the wildlife not to mention the history of each place we visited. I often wondered…how do these guys know all this stuff!! And in case you think it was all serious business, nothing could be farther from the truth. We had many moments of fun and laughter and even a couple of flute recitals just for a change of pace!!
In the end, I have Gianni to thank for this experience. His thoughtful organization and attention to detail were key in delivering a superb product, a memorable adventure and a trip of a lifetime. Walk About Tuscany is highly recommended! Grazie, Gianni

The Best Way to See Italy (Paula M., Oregon, USA)
Forget Rick Steves and sign on with Gianni for a wonderful exploration of some of the best Italy has to offer–countryside, history, food, and people. Gianni’s deep knowledge of all these adds so much richness to the experience of walking through picturesque medieval towns and gorgeous rolling hillsides of vineyards, fields and orchards. The accommodations were comfortable and centralized, often with wonderful views. Some of the food will absolutely spoil you for ever eating “Italian” food at home again. And the people we met through farm, winery and other small business visits were perhaps the best of all–passionate about the food they grow and so willing to share their experience. Although this was a tour through the areas surrounding Siena, Montalcino and Pienza, Gianni offers tours in other areas and I would expect the same high level of engagement and effort to provide unique experiences. Truly exceeded my expectations!

The unforgetable Tuscany (Paul L., Jakarta, Indonesia)
I am so amazed with Gianni who operated our tour with his in-depth knowledge of every single steps and buildings around Tuscany. Not to mention his creativeness in every moments of our walks. You will have great lunches and dinners with lots of special-2-thumbs-up wines. We also visit Olive Oil producer and given sampler at which is the best (and fresh) olive oil that I had ever tasted ! The scenery view is very awesome, just like the post card. Highly recommended and wouldn’t mind to do this tour again.

Simply the Best! (Susan, Oakville, Canada)
What an amazing and unforgettable experience! Our 8 day walk about Tuscany was like a walk through wonderland. Gianni somehow made each day better than the last. The scenery was magical, the food was incredible and the wine beyond words… Gianni’s vast knowledge and passion is undeniable. He is truly one of a kind as were the places we had the pleasure to visit (wineries, olive oil producer, cheese farm etc.). This is without a doubt the best way to see Italy. We had so much fun!

Group Tour of Tuscany Hill Towns with Walk About Tuscany Tours (Anne from Evanston, Illinois, USA)
I had a marvelous time on this trip. Our guide, Gianni, provided gorgeous walks and unique experiences with local organic producers of wine, produce, cheese, and olive oil. Definitely experiences I couldn’t have had without his guidance and that helped me to appreciate what makes this region unique. Gianni is knowledgeable and expended every effort to ensure that our trip was memorable and unique. We walked, ate very well, drank wonderful wines and learned a great deal about this region of Tuscany and why it is among the most delightful of all Italy.

Sharing double room

1900€ / person

Single supplement

+420€ / person

Solo traveler? If  you are a solo traveler and you don’t want to pay the single supplement we can try to match you with another solo traveler of the same gender to share the room, according to availability. If we cannot find a travel companion to share the room with you we will ask you to pay the single supplement.