2027 EARLY BIRD: SAVE € 100 EURO PER PERSON — BOOK BEFORE MAY 12
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2027 EARLY BIRD: SAVE € 100 EURO PER PERSON — BOOK BEFORE MAY 12
Explore Tuscany’s medieval towns and countryside with our guided walking tour. Discover Siena, Chianti, and San Gimignano. Enjoy leisurely strolls, family-run hotels, culinary delights, and local interactions. Choose between small group or private excursions for an unforgettable adventure.
Unveil Tuscany’s hidden gems: Siena, Chianti, San Gimignano, Montalcino, Pienza, and Val d’Orcia. Embarking on the Tuscany walking tour, you will wander ancient streets, savor regional delicacies, and soak up vibrant culture.
September 2025
from € 2895 / person
6 night stay at small hotels (3 and 4 stars). Book early and we will try to accommodate you in a room with a view.
All breakfasts, 5 lunches, 4 dinners. Local wine is always included with lunches and dinners. Vegetarian? Vegan? No problem!
Transportation along the tour
We carry your luggage from hotel to hotel
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
Chianti wine tasting and winery visit: you will talk to the owner!
Learn about saffron making or cheese making (according to availability) at a small farmhouse in Pienza
Learn how to tell the quality of extra virgin olive oil along an olive oil tasting
Full cooking class in an ancient building. A lot of fun!
All taxes
not included: transportation to the starting place and from the ending place of your trip
not included: tips for the guides
not included: 2 dinners when you are on your own along the tour
Gathering at the hotel’s lobby at 4:00 pm, we’ll commence our journey with an insightful tour introduction. Joined by an art guide, we’ll delve into Siena’s treasures – from the enchanting Piazza del Campo to winding alleys and the Palio horse race district’s museum. A delightful dining experience awaits at the family-owned Babazuf, where Marco and Chef Giovanni fuse traditional and modern Italian flavors.
Today, we venture into the stunning Chianti region, walking through rolling vineyards that have made Tuscany famous worldwide. At the end of our walk, we meet Giovanna, owner of Pacina Farm, who has dedicated her life to honoring the values of her father, Enzo—a pioneer of environmentalism in 1970s Italy and a former member of the Italian Parliament. Giovanna welcomes us into her world, sharing how her farm stands apart with its commitment to sustainable agriculture. Over lunch, we’ll taste her naturally produced wine, alongside a meal made entirely from farm-grown ingredients. A simple yet unforgettable experience, set in one of the most breathtaking places you’ll ever see. Later, we go back to our hotel for some rest. At around 6.30pm you will immerse yourself in a captivating cooking class at Dante Alighieri cooking school.
Venture to San Gimignano, a 45-minute transfer away. The town boasts 14 towering medieval marvels. Our countryside hike, enriched by olive groves and Vernaccia di Sangimginano vineyards, leads to Ganozzi family’s vegetable garden farmhouse. A delightful lunch sourced from their produce awaits. Returning to Siena, dinner is at your leisure.
A 50-minute drive takes us to Montalcino, famed for its wines. Wander its charming streets before embarking on a woodland walk. The path, adorned with Monte Amiata views, leads to Giacomo’s Il Cocco farm. Delve into wine wisdom with Giacomo as you explore his vineyard, Brunello in hand. A farm-fresh lunch follows. Transition to Pienza’s Corsignano Hotel. Tonight, savor dinner at a delectable Pienza eatery.
A short 15-minute transfer delivers us to Bagno Vignoni. After visiting, we embark on a 4-mile journey to the less-trodden San Quirico d’Orcia. Lunch at Osenna educates on quality olive oil and treats you to hand-made pici pasta with truffles. Explore San Quirico and its gardens before returning to Pienza. Dinner is yours to choose.
Set forth on foot from the hotel to Monticchiello, walking through wheat fields. Arrive at Santa Maria Farmhouse, specializing in saffron. Savor a sumptuous lunch celebrating local flavors and produce. Choose to return by foot or enjoy a drive back. The grand farewell dinner unfolds at an elegant international/Tuscany fusion restaurant.
* during some tours we instead go to Il Casale cheese farm, nearby Monticchiello, according to the availability. 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 and walk back to the hotel.
At 9:00 am, a 45-minute drive takes you to Chiusi-Chianciano Terme train station. From here, a train journey of about two hours leads you to Florence or Rome.
Please bear in mind that this is a typical itinerary, and the actual walks and sites may vary due to season, special events, or weather. We reserve the right to alter the itinerary since tour arrangements are made up to a year in advance, and in unforeseen circumstances that mandate changes may arise. Itinerary changes are made to improve the tour and your experience.
Day 1, 2 and 3 of our Tuscany guided walking tour welcome you to this inviting haven. Nestled just beyond Siena’s ancient city walls, La Villa is an exquisite “art nouveau” abode from the early 20th century.
A short stroll from Siena’s historic heart, it blends timeless elegance with modern convenience. Adorned with tasteful decor that honors its historical essence, this dwelling offers an ideal base to explore the medieval marvels of Siena. With a warm and welcoming staff, expect to feel right at home.
Explore more at: https://www.lavilladistr.it/en/home
Discover the allure of Corsignano Hotel in Pienza. Merging beauty with functionality, this newly renovated 4-star gem graces the canvas of Tuscany’s most pristine landscape.
Immerse yourself in a world of aesthetic charm and modern convenience. With an exceptional staff and a delectable breakfast spread, your experience here is destined to become a cherished memory of Tuscany’s essence.
Learn more at: https://www.hotelcorsignano.it/rooms/standard/?lang=en
Pici pasta is a type of traditional Italian pasta that originates from the Tuscany region. It’s characterized by its unique shape and rustic appearance.
Pici pasta is hand-rolled and typically made from just two simple ingredients: flour and water. The dough is rolled into thick, long strands that resemble rustic spaghetti. What sets pici pasta apart is its slightly uneven and thick texture, which allows it to hold onto sauces quite effectively.
The width of pici can vary, but it’s generally wider than standard spaghetti and has a chewy, hearty consistency when cooked. It’s often served with various sauces, such as tomato-based sauces, ragù, or simple garlic and olive oil, making it a versatile canvas for different flavor profiles.
Panzanella is a traditional Italian salad that originates from Tuscany. It is a delightful and rustic dish made primarily from simple ingredients like stale bread, ripe tomatoes, onions, fresh basil, cucumbers, and sometimes bell peppers.
The bread is a key component, as it’s typically soaked or lightly toasted to bring out its flavors and textures. The bread absorbs the juices from the tomatoes and any dressing used, making it soft and flavorful. The tomatoes provide a burst of freshness and juiciness, while the onions add a mild bite. Fresh basil contributes a fragrant and aromatic element, enhancing the overall taste. Additional vegetables like cucumbers and bell peppers can be added for extra crunch and color.
Panzanella is often seasoned with olive oil, vinegar (typically red wine vinegar), salt, and pepper. The dressing complements the natural flavors of the ingredients and ties them together into a harmonious and satisfying dish. It’s a perfect example of Italian cuisine’s knack for turning simple, humble ingredients into a delicious and satisfying meal.
Bruschetta is an Italian appetizer or antipasto dish that consists of toasted slices of crusty bread, typically made from rustic or country-style bread.
The bread slices are often rubbed with garlic and drizzled with olive oil before being toasted or grilled until they become crispy and slightly charred. Once the bread is prepared, it’s commonly topped with a mixture of fresh ingredients, which can vary but typically includes diced tomatoes, fresh basil, garlic, and sometimes onions.
The toppings are seasoned with salt, pepper, and additional olive oil to enhance the flavors. Bruschetta is known for its delightful combination of textures and flavors, offering a satisfying contrast between the crunchy bread and the fresh, aromatic toppings. It’s often served as an appetizer at Italian restaurants and is enjoyed for its simplicity, vibrant taste, and the use of high-quality, fresh ingredients.
Affettati is an Italian culinary term that refers to a variety of sliced, cured meats. These meats are typically thinly sliced and are often served as an appetizer or antipasto dish. Common types of affettati include prosciutto (cured ham), salami (cured sausage), bresaola (air-dried beef), and coppa (cured pork shoulder). The term “affettati” comes from the Italian word “affettare,” which means “to slice,” highlighting the importance of the thin slicing technique used to prepare these meats. These delicacies are enjoyed for their rich flavors and are often accompanied by cheeses, olives, and other accompaniments as part of a charcuterie board or platter.
“Roasted Ribs and Sausages” in English. It refers to a dish typically made with roasted pork ribs and sausages. The ribs and sausages are seasoned with various herbs, spices, and possibly marinades before being cooked in an oven or over an open flame until they are tender, flavorful, and have a crispy exterior. This dish is popular in Italian cuisine and often served as a hearty and savory main course.
Brunello di Montalcino is a type of red wine that comes from the Montalcino region in Tuscany, Italy. It’s known for its exceptional quality and is considered one of Italy’s finest and most renowned wines.
The wine is made exclusively from Sangiovese grapes, a traditional Italian grape variety known for its rich flavors and ability to reflect the characteristics of the terroir (environmental factors that influence the wine’s taste). The name “Brunello” translates to “little dark one” in Italian, referring to the deep, dark color of the wine.
Brunello di Montalcino is highly regarded for its complex aromas and flavors. It often exhibits notes of red and black fruits, like cherry and plum, along with herbal and earthy undertones. The wine typically undergoes a lengthy aging process, spending several years in oak barrels and then additional time in the bottle. This aging contributes to the wine’s depth, maturity, and ability to age gracefully over many years.
Due to its premium quality and limited production, Brunello di Montalcino is often associated with special occasions and is considered a collector’s item by wine enthusiasts. It pairs well with a variety of Italian dishes, especially those featuring rich flavors like roasted meats, game, and aged cheeses.
Giacomo at the winery “il Cocco” will show his grounds and cellar. You will love tasting Brunello at Il Cocco!
Price per person changes depending on the occupancy number of your private group.
More guests? Please ask us a quote. We can also slightly tailor the tour to your needs.
| Number of guests | price in double room (euros) | single supplement (euros) |
| 1 | contact us | |
| 2 or 3 | 4990 | 420 |
| 4 or 5 | 3990 | 420 |
| 6 or 7 | 3690 | 420 |
| 8 or 9 | 3550 | 420 |
| 10 or 11 | 3450 | 420 |
| 12 or more | 3350 | 420 |
| Number of guests | price in double room (euros) | single supplement (euros) |
| 1 | contact us | |
| 2 or 3 | 5230 | 420 |
| 4 or 5 | 4180 | 420 |
| 6 or 7 | 3690 | 420 |
| 8 or 9 | 3550 | 420 |
| 10 or 11 | 3450 | 420 |
| 12 or more | 3350 | 420 |
Siena – La Villa Hotel
Viale Vittorio Veneto, 11
53100 – Siena
4.00 PM
Chiusi – Chianciano Terme train station
10 AM
Walking or jogging for 60 minutes 3 times a week for 5 weeks ahead of trip will make your experience more enjoyable. In case you live in a flat area you might also incorporate some steps in your physical activity.
On a typical day you hike/walk with your guide in the morning for 3 hours, then we stop at a restaurant or farmhouse for lunch (lunch can last 1hour and half). We serve local food and wines as we believe that food plays an important role in the enjoyment of Tuscany.
In the afternoon there might be some more walking or town stroll. Around 4.30 or 5pm your guide will take you back to the hotel.
Your guides are available from 9am to 5pm on each day.
Before dinner you will be able to rest a couple of hours.
Dinner will be served in a restaurant in town that you will be able to easily reach on foot. At dinner the guide will not be with you. This is why we planned to have most of the hotels in the town centers and pedestrian areas. And if the hotel is away from the town center we have set up transportation to take you to the next restaurant or activity.
Local wine is always included for lunch or dinner. We serve vino della casa (house wine) as the quality of local house wines is very high. Not by chance this part of Tuscany is one of the most famous wine making area in Italy (Chianti Classico, Brunello, Vino Nobile di Montepulciano).
Month avg. High avg. Low
Apr 66 °F (19 °C) 46 °F (8 °C)
May 73 °F (23 °C) 54 °F (12 °C)
Jun 81 °F (27 °C) 59 °F (15 °C)
Sep 81 °F (27 °C) 59 °F (15 °C)
Oct 72 °F (22 °C) 52 °F (11 °C)
Nov 61 °F (16 °C) 45 °F (7 °C)
Do not feel obligated to tip your guides and drivers but if you wish to do so please remember that our dedicated tour guides and drivers work tirelessly to ensure you have a memorable and enriching experience during your journey. Tipping is a common practice to show appreciation for their hard work and expertise.
Plan to have extra cash or money in your credit card enough to buy a couple of coffee or tea every day (5 euros average) . Two nights out of six you are on your own for dinner (20-25 euros per meal per person, average)
The Only Way to Experience the Hilltop Towns of Tuscany! 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.
The Best Way to See Italy 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!
Walk about Tuscany Loved this tour and would highly encourage others to go. Our guides Gianni and Sara were great, everything ran smoothly from day one. Excellent choices of hotels, restaurants and walking trails. The perfect size group, lots of laughs and good memories. Looking forward to the next one. Grazie, Monica
Under the Tuscan Sun…and a big black cloud but only once 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 traveled 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 unforgetable Tuscany 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.
Group Tour of Tuscany Hill Towns with Walk About Tuscany Tours 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.
Terrain: Mostly flat or gently rolling terrain, with well-maintained paths and only occasional short uneven sections.
Distance: Usually shorter walks, around 4.5 to 5.5 km / 3 to 4 miles per day, depending on the itinerary.
Elevation gain: Very limited. There may be a few gentle slopes, but no significant climbs or descents.
Who it is for: Ideal for beginners, casual walkers, families, and anyone looking for a relaxed walking holiday with little physical effort.
Terrain: A mix of flat sections and more uneven ground, with some inclines, steps, or minor obstacles that remain manageable for most reasonably active travellers.
Distance: Generally around 5 to 8 km / 3 to 5 miles per day, depending on the tour and terrain.
Elevation gain: Noticeable but not demanding. Some uphill and downhill stretches may be present, though never steep or prolonged.
Who it is for: Suitable for beginners who want a slightly more active experience, as well as for regular walkers looking for a relaxed but rewarding pace.
Terrain: Varied terrain that may include uneven paths, longer walking sections, and regular uphill or downhill stretches.
Distance: Moderate daily walking time and distance, suitable for travellers who enjoy being active outdoors for a good part of the day.
Elevation gain: More consistent and clearly noticeable, though still within the reach of anyone with a basic to good level of fitness.
Who it is for: Best for active travellers who are comfortable walking for several hours a day and can handle some uneven terrain and sustained inclines.
