Siena, Chianti area, Pienza, Val d’Orcia are the quintessence of Tuscany. Tuscan Splendors Getaway will take you to the rolling hills, medieval monuments, cypress tree lines: this is what you expect from the postcard Tuscany.
Local people will invite you to enjoy their small farm. Trattorias will serve fresh delicious food and great local wine selections.
We have put the best of the best in Tuscan Splendors Getaway, in only 5 days! By booking this trip you will be able to start a good knowledge of Italian style and relaxed pace.
Local people are also a big part of this tour as we believe that the best memories will come from the people that you meet along this adventure.
Day 1 – Meeting in Siena and visit of Siena (Night at hotel in Siena)
We will meet the group at hotel’s lobby at 4.00pm. After a brief introduction about the tour we join an art guide to explore the city jewels (Piazza del Campo, streets and alleys and last but not least the museum of one of the districts of the Palio horse race). After the tour we will enjoy a pleasant restaurant called Babazuf. The restaurant is family owned: Marco and Giovanni (the chef) will host us with an interesting combination of traditional and modern Italian cooking style.
6 km = 3,7 miles (town stroll)
***La Villa Hotel – Siena
Day 2 – Chianti walk, winery experience. Cooking class in the evening (Overnight 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 boutique family run winery where you will meet Dario Castagno, NYTimes Bestselling author. Dario will guide you through the grounds and cellars of Fattoria Tregole, an organic farm perched in the heart of the Chianti Classico region already mentioned in a document date as far back as 1003 (!) While introducing you with fervor to all the products produced on its premises, at the same time he shall entertain you with plenty of fitting historical information and accounts regarding the home of the Chianti Classico. A that will explain to us how they make their wine so special. Lunch will follow at the nice restaurant owned by the Fattoria. A short transfer back to Siena. After a good rest we will enjoy a complete cooking class at Dante Alighieri cooking school.
8 km = 5 miles
***La Villa Hotel – Siena
breakfast – lunch – dinner
SHOW DAY 3, 4, 5
Day 3 – Bagno Vignoni and San Quirico (night at hotel in Pienza)
A 50 minutes transfer will take us today to Bagno Vignoni; we get off here. We visit Bagno Vignoni. Then we start our walk from here and after 4 miles we will reach San Quirico d’Orcia, a hidden and less frequented town. We then walk to the restaurant Osenna. At Osenna we will learn how to thell the difference between an extra virgin olive oil of quality and a bad olive oil. Then lunch goes on: the chef makes hand-made pici pasta. You don’t want to miss this pasta with fresh truffles. 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 on your own.
9 km = 5,5 miles
****Corsignano Hotel – Pienza
breakfast, lunch, dinner
Day 4 – Pienza walk to the farm – saffron farm or cheese making farm
After a generous breakfast we will start our walk directly from the hotel towards the town of Monticchiello. We pass through wheat fields. After a couple of hours walking we will reach the Santa Maria Farmhouse* that is specialized in the production of saffron. A nice lunch based on pappardelle with pecorino sheep cheese and cherry tomatoes, sausage and saffron and bread crumbs, 2 kinds of pecorino cheese and ricotta with honey and jam that is produced in the farm, white chocolate dessert with saffron and fruit and sangiovese wine from their production. After lunch you can decide to be driven back to the hotel or walk back to Pienza. Tonight the farewell dinner is at a posh international/Tuscany style 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.
9 km = 5,5 miles – optional afternoon walk of 7 Km = 4,3 miles
****Corsignano Hotel – Pienza
breakfast, lunch, dinner
Day 8 – Departure day
At 9.00 am 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).
note on the itinerary
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.
4 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, 3 lunches, 4 dinners. Local wine is always included with lunches and dinners. Vegetarian? Vegan? No problem!
Transportation along the tour
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
Full cooking class in an ancient building. A lot of fun!
La Villa Hotel – Siena
The group of Tuscany guided walking tour meets on day 1 at this cozy property. Located just outside the old city walls of Siena, The Villa is a charming “art nuveau” residence dating from the early years of the twentieth century and within easy walking distance from the historic centre of Siena. All our rooms are tastefully decorated with respect for the aesthetic and historical origins of the building. A great base from which to explore the medieval town of Siena.
The staff is very friendly and they will be able to make you feel at home.
Corsignano Hotel – Pienza
Beautiful & functional. It is completely newly renovated 4-star hotel, set in the frame of Tuscany’s most beautiful and unspoiled area. The staff is great, breakfast amazingly yummy. It will leave you a good memory of Tuscany.
|Number of guests||Price in double room (euros)||Single supplement (euros)|
|2 or 3||2850||390|
|4 or 5||2580||390|
|6 or 7||2360||390|
|8 or 9||2250||390|
|10 or 11||2145||390|
|12 or more||2030||390|
- deposit*300 EURO
- balance is due 95 days ahead of trip beginning date
- you can pay in instalments
Walk about Tuscany (Monica, South Africa) 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
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 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 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.
Founder, trip organizer and guide at Walk About Italy (with a degree in Geology)
I am 51 years old. Geology is my background (Ph.D.) but to me life is about more than an academic degree. Music and walking are my passions. I have been a certified guide for nature walks since 1999. After working many years as a guide and also in the back stage of the travel industry for foreign walking tour companies, I earned my Tour Organizer business license, valid in Italy and the rest of the world. Let me organize your vacation to Tuscany and other parts of Italy.
Tours he guides: Tuscany, Amalfi, Sicily, Umbria – Assisi & Le Marche
A true passion for life (with a degree in ethnology)
Sara is a fully licensed guide, both for nature trails and for the city of Siena. Sara was born in a small village in Chianti area. When I first met her few years ago I was struck by her great personality, enthusiasm and kindness. Her background is in Anthropology.
Tours she guides: Tuscany
Photographing Tuscany (with a degree in yoga teaching)
Rudy was born in Colle Val d’Elsa, a town between Siena and Florence. He began working as a cycling guide and then as a professional nature guide. He is a Yoga teacher and passionate about natural medicine. He studied kinesiology, shiatsu, craniosacral therapy and has completed a master’s degree in osteopathy. Now he is studying photojournalism and nature photography because he wants to combine four great passions: photography, travel, people, animals.
Rudy is a vegetarian. “In Tuscany you can eat well without meat too … especially if you like good red wine.”
Tours he guides: Tuscany and Amalfi
group meets here:
Siena – La Villa Hotel
Viale Vittorio Veneto, 11
53100 – Siena
trip ends here:
Chiusi – Chianciano Terme train station
at what time?
Useful information on the tour
How to prepare for this trip
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.
What to bring :
- Walking shoes with good traction (sometimes we might have mud on the trail)
- Hat, Swimming suit, sun cream, water bottle to refill with tap water
- Dinners at Italian restaurants do not require any special dress code.
Wear shoes with good traction
An average day of the trip
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).
In general, the climate in Tuscany is very mild. Usually summers in Tuscany are hot with little or no rain. July and August are the hottest months (but still nice for walking as there is always a breeze blowing up on the hills). Spring (April and May) and Autumn (October and November) are milder. You can have some drops of rain but not too many. Winter is colder but you still can count on many sunny days.
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)
Tipping your guides
Should you wish to tip your guides, the gratuity is entirely at your discretion. The standard in the industry ranges from 5€ to 10€ per person, per guide, per day. Tipping is not due to Gianni Stanghellini as he owns the company.
Tipping your drivers
Should you wish to tip your drivers, the gratuity is entirely at your discretion. The standard in the industry ranges from 1€ to 3€ per person, per driver, per day.
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 seven you are on your own for dinner (20-25 euros per meal per person, average)
Lots of activities!
In the Tuscany Guided Walking Tour we explore many medieval towns: Siena, Pienza, Vald’Orcia.
We taste oil, wine and vegetables at family-run farms…
…and we walk the many paths that connect the villages with memorable panoramas.
Music will accompany the tour from time to time.
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.
It is a small group tour
The group is not larger than 18
5 to 7 miles (3-4 hours average) walks on each day. WALK RATING: 2+ on a base of 1=easy to 5=strenuous
Every day a special activity
A music happening, hands-on cooking class, olive oil farm visit, wine family-run farm 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 book our tours you will give back a lot to the area, contributing to maintain the economy of this region. Thanks a lot for doing this!