DAY 1: Arrive Starting Point: Montepulciano
We recommend flying to Rome, Florence or Pisa and then catch the train to Chiusi (Train 1h30, 2h30 and 1h50 respectively). From Chiusi you can take the local bus or taxi the short distance to Montepulciano (20mins approx).
Overnight: B&B l'Agnolo
Located in the heart of Montepulciano. This once grand home is now a beautiful small and comfortable Bed and Breakfast, still displaying the ornate high fresco ceilings and wonderful surroundings. Expect a warm welcome during your stay in this unique bed and breakfast.;
DAY 2: Montepulciano to Pienza: 9.5 miles
Starting from the San Biagio church you follow a quiet dirt road to the charming village of Montichiello where you can pause for a relaxed lunch or perhaps just a quick cappuccino before continuing to Pienza. Pienza is a UNESCO World Heritage site because of it’s unique renaissance architecture and town planning. Additionally it is well known for the production of pecorino cheese and truffles.
Overnight: Hotel Pienza San Gregorio
Hotel Residence Pienza San Gregorio offers a tranquil retreat just meters away from the ancient walled town. Large comfortable rooms, a lovely restaurant serving traditional Tuscan food and an outdoor swimming pool combine to make this a favourite stop.
DAY 3: Pienza to Bagno Vignoni: 9.5 miles
Today you wander through a beautiful region of rolling hills, oak woods, cypress trees and pretty villages. The thermal baths complex at Bagno Vignoni is the perfect location to spend the afternoon relaxing.
Overnight: Albergo Le Terme or Agriturismo (Country Hotel)
Depending on availability you will stay at Albergo Le Terme, which is in the centre of town and is surrounded by steam from the thermal springs or a lovely agriturismo 2 km outside town on the trail.
DAY 4: Bagno Vignoni to Sant’Antimo: 8 miles
A hard but enjoyable day following dry riverbeds through a fairly wild environment brings you to St Antimo, an isolated abbey situated in a pastoral landscape. After exploring the abbey we will transfer you to the Medieval town of Montalacino.
Overnight: Hotel Dei Capitano - Montalcino
Hotel Dei Capitani is fantastically positioned in the centre of the Medieval town, offering wonderful panormaic views over the Tuscan landscape, from the beautifully designed swimming pool and terrac. You will experience warm Tuscan hospitality, in this charming Hotel.;
DAY 5: Montalcino to Buonconvento: 14 miles
A fairly tough but immensely rewarding final days walking in the famous Brunello wine region. You will pass tthrough vineyards and olive groves, then finally entering the beautiful Tuscan Landscape of the "Crete" and Buonconvento, where you will stay in a lovely agriturismo.
Overnight: Fattoria Pieve a salti -Buonconvento
For the next two nights you will stay at a traditional Tuscan agriturismo (country hotel), with a fabulous outdoor swimming pool, spa and various other activities on offer. The restaurant is ecxcellent, rustic in style and serving delicious food home grown on the estate.
DAY 6: Onward Travel From Buonconvento
We will transfer you to Buonconvento rail station where You can catch the train to Siena and then to the airport or perhaps your next destination in Italy.
Many of our clients choose to add extra nights along the walk to sample more of the wonderful walking and attractions available in Tuscany. If you choose to extend your holiday we would recommend spending extra nights in Montepulciano, Pienza or Montalcino.
If you wish to reduce the number of nights we can tailor your trip to your requirements.
Why not extend your time in Italy with a few nights in Florence, Rome or even Venice? We offer several short city extensions and would be happy to tailor one to your needs.
One of the highlights of this tour is the high standard of the accommodation. View Accommodation Details. We specifically choose the hotels and agriturismo (country hotels) to ensure that you enjoy every minute of your stay. All offer a warm Tuscan welcome to walkers, traditional hospitality and delicious local food and drink. Details of the lovely local hotels we normally use are detailed below.
We will always try and accommodate you at the locations detailed below, but because of limited availability we may have to accommodate you at an alternative location of the same or better standard. Alternative details will be noted on your accommodation sheet.
This independent walking holiday is not available to solo walkers. If you require single rooms in your party we will of course try to accommodate your request, subject to availability and payment of a single supplement.
The delicious Tuscan food and wine available locally is undoubtedly a highlight of this holiday. The price of your holiday includes a hearty breakfast each morning. Lunch and dinner are not included so you are free to choose from the available options. Most of your accommodations will more than happy to provide a packed lunch on request and this can be booked on arrival. Alternatively your route includes details of local shops and convenient lunch stops on the way. Dinner is available either at your accommodation or nearby restaurants.
Your bags will be collected from your accommodation each day and moved onto your overnight accommodation. We ask you to limit your luggage to one bag of up to 20kg per person.
Your information pack has a detailed equipment list which includes standard walking gear such as good walking boots or shoes, warm and waterproof clothes and a day pack.
Tuscany & Umbria—Lonely Planet Regional Guides
Under The Tuscan Sun—Frances Mayes
Many of our clients choose to add extra nights along the walk or at the start/end of the walk. These can be added at the time of booking.
B&B l'Agnolo - Montepulciano
located in the heart of Montepulciano. This once grand home is now a beautiful small and comfortable Bed and Breakfast, still displaying the ornate high fresco ceilings and wonderful surroundings. Expect a warm welcome during your stay in this unique bed and breakfast.
Hotel Marzocco - Montepulciano
The Hotel Il Marzocco has been operating as a hotel since 1860 and operated by the same family since 1900. It has the welcoming and refined atmosphere of a large country house and is furnished with genuine XIX century furniture.
Residence San Gregorio - Pienza
Residence San Gregorio is situated a few hundred meters away from the ancient walled town of Pienza, in the heart of Tuscany. The Hotel Residence San Gregorio is an ideal exclusive environment to spend a night or a few days immersed in the magical atmosphere of a renaissance town, considered to be an architectural jewel.
Hotel Le Terme - Bagno Vignoni
Surrounded by the warm steam from the thermal spring, continuing the legend of healthy water, one finds the ancient construction of the Rossellino, home of Pope Pius II Piccolomini, today know as the Hotel "Le Terme". The rooms are decorated in classical style and the restaurant specialises in traditional Tuscan style food where simple ingredients are combined into delicious dishes. All complimented by delicious wines from the surrounding villages.
Hotel Dei Capitani - Montalcino
Hotel Dei Capitani is fantastically positioned in the centre of the Medieval town of Montalcino. You will delight in the wonderful panormaic views over the Tuscan countryside, from the beautifully designed swimming pool and terrace area. You can expect a warm welcome during your stay in this charming Hotel.
Hotel Il Giglio - Montalcino
A charming retreat in the heart of Montalcino, a family-run Hotel in a warm and quiet building, facing a gorgeous landscape over the Tuscan countryside. This is “Il Giglio”. The hotel has just 12 rooms, each one with cast-iron bed frames, painted ceiling and travertine stone bathrooms in a harmonious blend of rustic Tuscan style and classical elegance. The breathtaking panorama through the windows contributes to create an atmosphere that can only be experienced, never described.
Fattoria Pieve a Salti - Buonconvento
A traditional Tuscan agriturismo, offering total tranquility and overlooking the incredibly beautiful Tuscan countryside. Enjoy the vast array of facilities on offer, with outdoor swimming pool, spa, horseriding and the rustic restaurant which seves excellent home grown food from the estate.
Getting to Chiusi
We recommend you fly to Rome, Pisa or Florence and catch the train to Chiusi. Trains run regularly and take 1h30, 2h30 or 1h50 respectively and cost approx 22 Euro from Pisa. Tickets can be booked on arrival or online prior to departure. Visit www.trenitalia.it for times, prices and booking.
Parking at additional cost can be arranged in advance if you are driving.
Getting from Buonconvento
Trains run regularly from Buonconvento to Siena (25mins) where you can change trains to reach the airport at Pisa (2h10, 8.90Euro) or Florence (1h30 6Euro).
We are often asked the following questions and I hope that you will find the answers useful.
Please do not hesitate to contact us if you have any other questions or for more advice from our team.
How fit do I need to be?
This walking holiday is graded moderate and involves 3 - 7 hours of walking each day so you should enjoy an active lifestyle to get the most from this holiday. If you are unable to walk on any day you can use taxis or public transport to move onto the next night's accommodation.
When is the best time of year?
Spring in Tuscany is sublime and April, May and June are absolutely lovely. Autumn is probably my favourite time of year as the landscape is made up of a gold and red pallet so September and October are unmissable. July and August can be very hot so you will have to start early to miss the heat of the day, although the towns and villages are buzzing which is great. You can view weather details for the region here.
How far in advance do I need to book?
We suggest you book as soon as your plans are finalised Tuscany is extremely popular especially during July/August. You will find up to date availability on our website and we will always try and accommodate your plans so just ask.
What personal equipment do I need?
You will need good walking shoes/boots, comfortable walking clothes, waterproof jacket and trousers, a daypack and hats/gloves etc. You can download a full equipment list from the downloads page of our website.
Which is the best airport?
Either Pisa, Florence or Rome are convenient and you can reach the start/end of the walk by train in an hour or two.
The Hill Towns of Tuscany Highlights is available from March to November in the months coloured green. You can start your holiday on any date in the season. To make a provisional reservation select "Book" for the itinerary you are interested in.
Option prices will be displayed as part of the booking process.
Because every walking holiday we book is bespoke, availability changes from day to day and our booking process works as follows:
- You provisionally book the tour you are interested in for your preferred dates and pay a 20% deposit online or by phone.
- We confirm availability and book all your accommodation and options and send final confirmation as soon as everything is confirmed (max 5 working days).
- If we are unable to accommodate you on your confirmed dates/tour or an alternative of your choice your deposit is fully refunded.
||Hill Towns of Tuscany Highlights
||6 Days & 5 Nights
Personal briefing on arrival and support from our local representative if required.
- 5 Nights accommodation including breakfast in ensuite rooms in hotels or agriturismo.
- Daily door to door baggage transfer.
- A detailed info pack, route notes and map for your group leader.
- Transfers as detailed in the itinerary.
- Emergency telephone support from our office in the event of a problem.
Travel to the start (Chiusi) or from the finish (Buonconvento) of the walk.
- Lunches, dinners, snacks and drinks.
- Travel Insurance.
- Taxi transfers or public transport should you need to skip a stage.
Single room supplement.
- Extra nights before, during or afer your walk.
- Private airport transfers.