Tuscan Splendors 2023

Tuscan Splendors 2023

SCHEDULED GROUP SIZE: min 1 – max 18 guests PRIVATE GROUP SIZE: min 1 – no limit DURATION: 7 Days & 6 Nights

  WALK RATING: 2+   HOTEL STYLE: very comfortable to stylish

CLOSEST AIRPORTS: Florence (FLR) and Rome (FCO)


Scheduled tours

2023 dates


  • May 11-17
  • June 6-12
  • June 21-27
  • September 8-14 (full)
  • September 27 – October 3
  • October 3-9, 2023

Private tours

price p/p: varies according to group size. Check Price below here

Departures: anytime


During our Tuscany Guided Walking Tour we will show you around amazing medieval towns and stunning surrounding countryside: Siena, Chianti region, San Gimignano, Montalcino, Pienza, Val d’Orcia. You will travel with a small group.

Each day we walk for about 2-3 hours with lots of stops for guide commentaries, coffee, pastries, visit , lunches at small family-run farms combined with amazing wineDinners will be held in small trattorias.
Music will accompany the tour from time time.
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.

You can travel with a small group or privately. You choose!



  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

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

Full cooking class in an ancient building. A lot of fun!

 All taxes



Tuscany hotel

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.


Tuscany hotel

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.



tuscany walking tour
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, 6, 7
Day 3 – San Gimignano walk (Night at hotel in Siena)

Today we will explore the area of San Gimignano. The transfer from the hotel takes about 45 minutes. The town still has 14 high medieval towers. The 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. We then drive back to the hotel. Dinner tonight is on your own.

11 km = 7 miles with shorter options
***La Villa Hotel – Siena
breakfast – lunch


Day 4   Montalcino and Brunello Il Cocco winery experience

It’s transfer day! We drive for 50 minutes to Montalcino. We will visit the streets and alleys of this famous place for wine making. The town itself is very pretty. Then we start our country walk. 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 Giacomo. Giacomo 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  drive to our new hotel in Pienza. Tonight dinner is at a delicious restaurant in Pienza.

9 km = 5.5 miles – optional afternoon walk of 4 Km = 2.5 miles
Corsignano Hotel in Pienza
breakfast – lunch, dinner


Day 5   Bagno Vignoni and San Quirico.

A 15 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 6   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 7 – 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.


2450 EURO p.p. (sharing double room)

590 EURO p.p. (single supplement only in case you need your double room for single use)

      • deposit 300 EURO p.p.
      • balance is due 95 days ahead of trip beginning date
      • you can pay in instalments
Number of guests price in double room (euros) single supplement (euros)
1 contact us  
2 or 3 3840  590
4 or 5 3070 590
6 or 7 2960 590
8 or 9  2850 590
10 or 11 2800 590
12 or more 2690 590
More guests? Please ask us a quote. We can also tailor the tour to your needs.
  • deposit 300 EURO p.p.
  • 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



Farming vegetables, olives, chickens, ducks and pigs (with a degree in natural sciences)

Chiara was born in Volterra, a charming Etruscan town nearby Pisa. After graduating in Natural Sciences in 2001 she has become a nature hiking guide, accompanying guests in Tuscany and pleasing them with lovely pic-nics. In 2015 she decided to start her own farm with a vegetable garden, olive trees, aromatic plants, chickens, ducks and pigs. Now she is a tour leader and a farmer. She will take you around with dirty hands for a good reason!

Tours she guides: Tuscany



Making pecorino sheep cheese an art (with a degree in natural sciences)

Daniele was born and raised in a farmhouse in the Tuscan countryside. Ever since he helped his dad to make an amazing pecorino sheep cheese.

He’s got a Master’s Degree in Natural Sciences in 2009 and started working as a nature guide around the Indian Ocean and Africa, before coming back to his beloved homeland.

As a passionate birdwatcher, he always keep an eye on the sky during his walks, sharing the pleasure of exploration and the discovery of new places.

Tours he guides: Tuscany



Walking changed my life!

Erica was born in San Gimignano from Italian dad and Scottish mum.

Her background is as Sales Executive in an export company but after 10 years she decided to leave the office, change her life and make a job out of her passions: walking, nature, art, living outdoor and meeting new people and cultures. Now Erica is a licensed hiking and city guide and her aim is to let you love Tuscany as much as she does!

Tours she guides: Tuscany

Trip facts

group meets here:

Siena – La Villa Hotel
Viale Vittorio Veneto, 11
53100 – Siena

at what time?

4.00 PM

trip ends here:

Chiusi – Chianciano Terme train station

at what time?

10 AM

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.


Extra expenses

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)

Snapshots from the tour

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TUSCANY Sept 4-11 - CINQUE TERRE Sept 17-23 (6 night gap)


AMALFI COAST Oct 10-16 - CINQUE TERRE Oct 17-23 (1 night gap)


CINQUE TERRE Sept 17-23 - SICILY Sept 25- Oct 1 (2 night gap)
SICILY Oct 9-15 - 5 TERRE Oct 17-23 (2 night gap)


UMBRIA MARCHE Oct 10-16 - 5 TERRE Oct 17-23 (1 night gap)



The nights of gap are not included.
We will provide suggestions for places to visit and stay in between the two tours.


TUSCANY May 10-17 – AMALFI COAST May 18-24 (1 night gap)
TUSCANY Sept 4-11 – AMALFI COAST Sept 12-18 (1 night gap)
TUSCANY Oct 2-9 – AMALFI COAST Oct 10-16 (1 night gap)
AMALFI COAST Oct 10-16 – TUSCANY Oct 16-23 (no night gap)


TUSCANY Oct 2-9 – SICILY Oct 9-15 (no night gap)
SICILY Sept 1-7 – TUSCANY Sept 11-18 (4 night gap)
SICILY Sept 25-Oct 1 – TUSCANY Oct 2-9 (1 night gap)
SICILY Oct 9-15 – TUSCANY Oct 16-23 (1 night gap)


UMBRIA MARCHE May 3-9 – TUSCANY May 10-17 (1 night gap)
TUSCANY Sept 11-18 – UMBRIA MARCHE Sept 19-25 (1 night gap)
TUSCANY Oct 2-9 – UMBRIA MARCHE Oct 10-16 (1 night gap)
UMBRIA MARCHE Oct 10-16 – TUSCANY Oct 16-23 (no night gap)


TUSCANY Sept 4-11 – CINQUE TERRE Sept 17-23 (6 night gap)


AMALFI COAST May 18-24 – SICILY May 25-31 (1 night gap)
SICILY Sept 1-7 – AMALFI COAST Sept 12-18 (5 night gap)


AMALFI COAST Sept 12-18 – UMBRIA MARCHE Sept 19-25 (1 night gap)


AMALFI COAST Oct 10-16 – CINQUE TERRE Oct 17-23 (1 night gap)


UMBRIA MARCHE Sept 19-25 – SICILY Sept 25-Oct 1 (no night gap)


CINQUE TERRE Sept 17-23 – SICILY Sept 25- Oct 1 (2 night gap)


SICILY Oct 9-15 – 5 TERRE Oct 17-23 (2 night gap)


UMBRIA MARCHE Oct 10-16 – 5 TERRE Oct 17-23 (1 night gap)


Activity level:
2+ (on a scale from 1 to 5)
Daily Hours:
Up to 3
Daily Distance:
3 to 10 km (2 to 7 miles)
Walking Surfaces:
Gentle with some uneven terrain
Daily Elevation:
Up to 200 mt. (650 feet)
Personal Fitness:
Light exercise weekly, active lifestyle


Activity level:
3 (on a scale from 1 to 5)
Daily Hours:
Up to 3
Daily Distance:
3 to 10 km (2 to 7 miles)
Walking Surfaces:
Gentle with some uneven terrain
Daily Elevation:
Up to 300 mt. (1000 ft.) - Average day 200 mt (650 ft.)
Personal Fitness:
Light exercise weekly, active lifestyle