Southern Tuscany – Independent
Walk south-east of Siena, one of the best-preserved medieval cities in the world, through the crete, an area that has escaped the attention of many tourists. This open, rolling landscape changes from a sea of green wheat in spring to an enigmatic, lunar-like landscape in the summer and autumn.
In places, these spectacular hills feel surprisingly wild, cut by dramatic ravines and gulleys. Along the route explore a string of superb medieval Tuscan hill towns and villages containing a fine array of secular and religious architecture. Add to this the excellent food and famous wines of the region, including Chianti, Brunello from Montalcino and Vino Nobile from Montepulciano.
Duration: 5, 6, 8, 9 or 10 days
Itinerary
The best-preserved great medieval city in Europe. Magnificent cathedral, the Piazza del Campo (setting for the Palio horse race) and an abundance of outstanding 14th and 15th century art and architecture.
Radiating from the magnificent Piazza del Campo, Siena is one of the most perfectly preserved medieval cities in Europe. Visit the stunning Duomo (cathedral) incorporating the Libreria Piccolomini. Opposite lies Santa Maria della Scala - an ex-medieval hospital with frescoes and half a dozen small museums that stretch through tunnels inside it.
Simple hotel in medieval city centre
18th century villa, close to the historic centre
Walk south from Siena following the route of the early medieval Via Francigena, across the open hills of the crete, a lunar-like terrain, to Lucignano (14.3 miles, 7.5 hours).
A tiny, fortified, brick-built hamlet (borghetto), typical of the medieval defensive settlements that are scattered across the countryside south of Siena. Visit the large 13th century gates and the Romanesque church of San Giovanni Battista.
Friendly, family run hotel with excellent restaurant
Walk through pastures, vineyards and olive groves overlooking the Arbia and Ombrone valleys, to walled Buonconvento, with its small museum housing 14th/15th century masterpieces (10.7 miles, 5.5 hours).
NB If you opt for the 5 or 6 day itinerary which includes a 1 night stay in Buonconvento, you will stay at Il Ghibellino hotel or if you opt for the 8, 9 or 10 day itinerary which includes a 2 night stay in Buonconvento, you will stay at Fattoria Pieve a Salti.
Charming yet unpretentious, the walled brick-built town lies on the ancient Via Cassia route. It has a fine gate, a series of delightful small side streets to explore, a small but superb collection of Sienese masterpieces and a fascinating museum of rural labour and traditions.
In a beautiful setting, with indoor and outdoor pools
Family-run hotel in the centre of town (for 1 night stays in Buonconvento)
Walk to visit one of the finest abbeys in Europe - the Benedictine Monte Oliveto Maggiore, with its superb cloister of magnificent frescoes by Signorelli and Sodoma (return journey 11.6 miles, 6 hours).
Monte Oliveto Maggiore is a Benedictine abbey, still maintained today by a small group of monks. Within its cloisters discover superb late 15th / early 16th century frescoes.
In a beautiful setting, with indoor and outdoor pools
Over open hills and through the famous vineyards of Brunello to panoramically situated Montalcino, centre of the Brunello wine area (11.4 or 13.1 miles, 5.5 or 6.5 hours).
Inhabited since Etruscan times, this little medieval town boasts a spectacular location and a splendid fortress. A friendly and welcoming town, with some attractive shops and bars, and home of one of Italy’s most famous and finest wines – Brunello di Montalcino. Montalcino’s sacred art museum is very highly rated by all who visit.
Superb views and small pool in summer
Walk through the vineyards of Brunello to the superb Romanesque abbey-church of Sant’Antimo, built of alabaster and onyx. Then on to the Orcia Valley and Bagno Vignoni, with its Roman thermal baths in the central piazza (11.2 or 14.1 miles, 5.5 or 7 hours).
The central piazza of this picturesque town is a thermal pool where Romans rested and bathed en route north along the Via Cassia. Today you are not allowed to bathe here but you can take the waters in the nearby springs. The Renaissance arcaded area at the near end was built by the Medici who, like the Romans and Catherine of Siena before them, took the sulphur cure here.
Modern hotel overlooking Roman baths
Walk along the Orcia Valley then across open farmland to Pienza, birthplace of Aeneas Piccolomini. When he was elected as Pope Pius II in 1458, he commissioned the architect Rossellino to convert his birthplace into the first Renaissance city. A five-minute walk from end to end, Pienza has a delightful papal palace, ‘cathedral’ and museum (5.8 miles, 2.5 hours).
A compact and delightfully remote little town perched on a hillcrest, with impressive views over the plains of southern Tuscany to Monte Amiata. A perfect miniature of Renaissance order and urban structure, significantly rebuilt around 1460 on the orders of Pope Pius II, who was born there. It has a fine cathedral, a palace of faded grandeur and an excellent museum of sacred art. It is also famed for its cheese production and hops!
Converted theatre close to centre with swimming pool
Converted monastery with views and pool in summer
Continue walking to Montepulciano or Montefollonico (upgrade accommodation). To Montepulciano: Walk to the centre of the Vino Nobile di Montepulciano wine district via the church of San Biagio and explore Montepulciano’s fine palazzi, cathedral, frescoed churches and museum (8.3 miles, 4 hours). Or, to Montefollonico: Follow strade bianche and farm tracks through quiet countryside to stay at a delightfully restored ancient olive mill (8.7 miles, 4.5 hours).
Montepulciano: Small yet magnificent, a Renaissance city boasting several fine churches and works of art. Fine palazzi, cathedral, frescoed churches and museum with Della Robbias. It is the home of one of Italy’s much praised wines – Vino Nobile di Montepulciano.
Montefollonico: Small pretty village perched high above the valley.
Small guest house in the historic centre of Montepulciano
(breakfast available in café opposite)
Historic country hotel with pool, restaurant and wonderful panoramic views
Free day to enjoy La Chiusa and/or an optional walk to Montepulciano. From La Chiusa you can either skirt below Montefollonico following a small lane, or go up through Montefollonico and down a lovely path through woods. The two routes merge beyond the village to follow farm tracks then strada bianca (gravel tracks) across fields to climb via the wonderful church of San Biagio to Montepulciano (4.5 miles / 2-2.5 hours).
Montefollonico is a small, tranquil medieval hilltop village surrounded by vineyards and olive groves, located on a ridge with panoramic views across the Tuscan countryside. The village dates to around 1000 and features ancient walls, a fortified castle and 12C church of San Leonardo.
Historic country hotel with pool, restaurant and wonderful panoramic views
Trip Planner
Walking & Terrain
Walking: Moderate to Challenging. Harder sections include a steep climb up to Montalcino, a climb up to Pienza and a long day of walking to Bagno Vignoni traversing some relatively wild countryside and rougher ground. The walk lengths vary from 2.5 hours to a maximum of 7 hours walking. Hours of walking, which may vary from individual to individual, means hours of actual walking and does not include stops for lunch, sightseeing or rests.
Terrain: Follow a wide variety of paths, from dirt roads and farm tracks to wooded paths and ancient drove roads. For those planning an autumn trip, be prepared to cross one or two roughly ploughed fields. On certain days paths may cross a more rugged terrain or ground that is muddy in wet weather – please make sure that your footwear provides sufficient ankle support. There are no vertiginous sections.
All ATG trips include facilities and options so that you can arrange to walk as much or as little as you like – or not at all - and your Route Manager will be able to advise you on public transport or taxi options.
Walking & Terrain
Walking: Moderate to Challenging. Harder sections include a steep climb up to Montalcino, a climb up to Pienza and a long day of walking to Bagno Vignoni traversing some relatively wild countryside and rougher ground. The walk lengths vary from 2.5 hours to a maximum of 7 hours walking. Hours of walking, which may vary from individual to individual, means hours of actual walking and does not include stops for lunch, sightseeing or rests.
Terrain: Follow a wide variety of paths, from dirt roads and farm tracks to wooded paths and ancient drove roads. For those planning an autumn trip, be prepared to cross one or two roughly ploughed fields. On certain days paths may cross a more rugged terrain or ground that is muddy in wet weather – please make sure that your footwear provides sufficient ankle support. There are no vertiginous sections.
All ATG trips include facilities and options so that you can arrange to walk as much or as little as you like – or not at all - and your Route Manager will be able to advise you on public transport or taxi options.
Additional activities available locally
This is a wonderful area offering additional local experiences - some can be booked to fit in with your chosen itinerary, whilst for others you may wish to customise your trip to have an extra leisurely day or two to enjoy.
Additional activities are paid for locally and can be booked via your Route Manager who will contact you 2 weeks prior to departure.
Siena - ATG offers a 3.5 hour city walk taking in the highights of Siena. If you are interested in art & architecture, we’d recommend more time here to enjoy all that this medieval city can offer including an abundance of 14C and 15C art and architecture, from the famous Piazza del Campo, scene of the Palio horse race, to galleries filled with iconic medieval masterpieces, and the great cathedral.
Montalcino - Wine Tasting, prices from 40€/person
Buonconvento - Visit to the Abbey of Monte Oliveto Maggiore. This is included in the 8 day itinerary or if you are considering the 5 day itinerary, a visit is possible with a very early start or alternatively extend your stay by an extra day to enjoy this excursion on foot.
Montefollonico - Experiences at La Chiusa. If you opt to include a stay at La Chiusa in Montefollonico, the hotel offers guests a range of experiences including cooking classes, wine, beer and cheese tasting, horse-riding, biking, massage and a bee experience.
Your Personal ATG Route Manager
I grew up in Poland and have had the wonderful opportunity to study and work in Italy. Since 2018, I’ve been part of ATG and, right now, I’m enjoying life in beautiful Tuscany! What I love most about my job is the chance to explore so many amazing parts of Italy including hidden gems that aren’t typically on tourists’ radar. It really feels special to experience the authentic charm of Tuscany with its rolling hills, vineyards and picturesque countryside and I look forward to welcoming you.
"Monika was excellent throughout the trip."
Route Book
The ATG Route Book is a detailed, day-to-day guide. The book anticipates your needs with easy-to-follow instructions, maps, plans and other information that will guide you to discover the best that the area has to offer and is the key to the success of an independent holiday with us.
Walking App
Your Route Manager can provide you with a link to download an app to your smartphone. This app provides the GPS track for your route on your phone. You can use this digital support to find your position and navigate the route, even without an internet connection or mobile phone reception.
Accommodation & Meals
You can expect each hotel to be one of the most characteristic, comfortable and best located for travellers on foot, with the character and sometimes the standard varying from place to place.
Star ratings indicate official classification, although many delightful places have no star rating. In more remote areas hotels may be of a generally lower standard in relation to their ‘star ratings’.
Single travellers are accommodated in double rooms for single occupancy for a supplemental charge.
On this route, upgraded accommodation is available at some overnight stops, as specified on the itinerary.
Breakfast is included and there are suggestions in the Route Book about where to buy provisions for a picnic lunch, as well as restaurant recommendations. Dining options often include a choice of restaurants that can be pre-booked for you by your Route Manager.
Food & Wine
Tuscan food is simple and earthy. Menus feature rich bean soups, bread served alongside salamis and tangy sheep cheeses, slow-cooked wild boar or rabbit stews and spiced cakes full of candied fruits and nuts. This all complements the robust red wines of the region. Finish with a glass of the delicious local ‘passito’ dessert wine, Vin Santo, served with almond cantucci biscuits on the side. Many of the villages visited en route have a selection of enoteca, or wine shops, for tasting and buying wines. You will also pass wine estates where sampling and direct sales are possible. Good ‘foodie’ gifts include local olive oil, dried wild mushrooms, Tuscan meats and cheeses, and ricciarelli, or Sienese macaroons. The Route Book contains a section on the cuisine and wines of the region, and a list of recommended restaurants en route. The Route Manager will be pleased to help you with any queries, requests or advice.
History
The history of Tuscany has been one of invasion and conquest from earliest times. Yet interspersed within these periods of war and rivalry were times of great cultural, political and economic brilliance. These were most notably during the Etruscan period from the 8th century BC, and then from the 12th century when many Tuscan cities prospered finding great wealth through new-found trades. The incredible riches that accumulated laid the foundations for the Renaissance, the seismic cultural movement that began in Florence and then spread throughout Europe. Our Route Book provides further detailed pages on the history of Tuscany.
Flora & Fauna
There are delightful woodland and wayside flowers in spring as well as plenty of birdlife. In May and June you can enjoy poppy fields and fireflies. In late June to July there are bright displays of sunflowers and butterflies. Autumn sees cyclamen flowering again in the woods and the vendemmia or grape harvest. Our Route Book provides further detail while apps such as ‘LeafSnap’, ‘Flora Incognita’, ‘ChirpOMatic’ and child-friendly ‘Seek by iNaturalist’ can identify the flora and fauna en route.
Travel arrangements
Travel arrangements, including flights, for ATG Independent Footloose trips should be made independently.
Outward travel to Siena:
From Pisa airport, take the ‘People Mover’ shuttle train to Pisa Central station, and a train from there to Siena, changing trains at Empoli.
From Florence airport, take the tram line to the main train or bus station in central Florence. There are regular direct trains or express buses from here to Siena.
From Rome Fiumicino, either take a taxi or the Leonardo Express shuttle train to Roma Termini station in the city centre. From here there are frequent trains to Siena, but costs and journey times vary.
Outward travel to Buonconvento:
Same as above, but you will need to change trains at Siena onto a train to Buonconvento. From Rome Fiumicino airport there are direct trains to Buonconvento but they vary considerably in timing and routing.
Return travel:
Take a bus or taxi to Buonconvento station, then a train to Florence SMN station and an onward tram to Florence airport. From Buonconvento there are also trains to Pisa central. For Rome, take a taxi to Chiusi-Chianciano Terme station for onward trains.
Trip Options & Prices
Overview
This 5 day independent walking tour in Tuscany starts in Buonconvento, 16 miles south of Siena, and includes 3 days of walking. Discover the famous Brunello vineyards, Romanesque Abbey of Sant’ Antimo and iconic hilltop towns of medieval Montalcino and Renaissance Pienza on this short break to Italy.
Itinerary
Day 1: Arrive in Buonconvento
Day 2: Buonconvento to Montalcino
Day 3: Montalcino to Bagno Vignoni
Day 4: Bagno Vignoni to Pienza*
Day 5: Departure
*The upgrade price option includes upgrades at these locations
Prices (per person)
Overview
This 6 day independent walking tour in Italy offers everything on the 5 day itinerary plus an additional walk to either the medieval walled town of Montepulciano or to Montefollonico with the opportunity to stay in an historic converted olive mill with pool. A short trip discovering the wine areas of Brunello di Montalcino & Vino Nobile di Montepulciano.
Itinerary
Day 1: Arrive in Buonconvento
Day 2: Buonconvento to Montalcino
Day 3: Montalcino to Bagno Vignoni
Day 4: Bagno Vignoni to Pienza*
Day 5: Pienza to Montepulciano / Montefollonico*
Day 5: Departure
*The upgrade price option includes upgrades at these locations
Prices (per person)
Overview
This 8 day independent walking tour is a more in-depth visit of the area starting in the medieval town of Siena. The itinerary includes 5 days walking plus an excursion on foot to the superb Benedictine abbey of Monte Oliveto Maggiore. Discover historic towns, art and wine as you walk through rolling Tuscan landscapes on this weeklong trip to Italy.
Itinerary
Day 1: Arrive in Siena*
Day 2: Siena to Lucignano
Day 3: Lucignano to Buonconvento
Day 4: Buonconvento - free day
Day 5: Buonconvento to Montalcino
Day 6: Montalcino to Bagno Vignoni
Day 7: Bagno Vignoni to Pienza*
Day 8: Departure
*The upgrade price option includes upgrades at these locations
Prices (per person)
Overview
This 9 day independent walking holiday includes everything on the 8 day itinerary plus a walk on to Montepulciano or Montefollonico. Enjoy a longer trip walking through three of Italy’s greatest wine areas: Chianti, Brunello di Montalcino & Vino Nobile di Montepulciano.
Itinerary
Day 1: Arrive in Siena*
Day 2: Siena to Lucignano
Day 3: Lucignano to Buonconvento
Day 4: Buonconvento - free day
Day 5: Buonconvento to Montalcino
Day 6: Montalcino to Bagno Vignoni
Day 7: Bagno Vignoni to Pienza*
Day 8: Pienza to Montepulciano / Montefollonico*
Day 9: Departure
*The upgrade price option includes upgrades at these locations
Prices (per person)
Overview
This 10 day independent walking is our most extensive visit of the area. It includes everything on the 9 day itinerary with an extra day in Montefollonico to enjoy the facilities and activities available at La Chiusa and/or an optional walk to Montepulciano.
Itinerary
Day 1: Arrive in Siena*
Day 2: Siena to Lucignano
Day 3: Lucignano to Buonconvento
Day 4: Buonconvento - free day
Day 5: Buonconvento to Montalcino
Day 6: Montalcino to Bagno Vignoni
Day 7: Bagno Vignoni to Pienza*
Day 8: Pienza to Montefollonico*
Day 9: Montefollonico* - free day
Day 10: Departure
*The upgrade price option includes upgrades at these locations
Prices (per person)
Our Independent Footloose itineraries have the flexibility to be customised if you would like to spend more time in any of the places en route; perhaps to incorporate some of the add-ons available locally or just to create a more relaxed pace to your holiday.
If you wish to build your own itinerary please complete our customise form and our Sales team will provide you with a bespoke quote.
Frequently Asked Questions
On each route there is an ATG Route Manager, who is there to take care of all the practicalities and ensure the success of your trip. Route Managers have all been ATG-trained, speak English and the language of the country fluently, and live in the local area. Your Route Manager will make contact with you a couple of weeks prior to departure (usually by email) and will then meet you at the start of your trip and will be available during your trip to move your luggage from hotel to hotel, provide local information, make restaurant reservations and do everything possible to ensure that you derive maximum enjoyment from your holiday.
Please let us know about any dietary restrictions or allergies in advance so that our Route Manager can ensure that you are catered for during your holiday. Most dietary restrictions do not present a problem on our trips and the Route Manager can discuss your requirements in more detail with you at the start of your trip.
The walks are graded according to difficulty but you can walk as much or as little as you like.
Easy: walking along well-established paths and tracks with some short ascents/descents. These trips are suitable for most people who enjoy occasional exercise.
Easy to Moderate: walking along well-established paths and tracks. Occasional loose (gravel) surfaces. Ascents/descents up to 1 hour. These trips are suitable for most people who have a reasonable level of fitness.
Moderate: walking along a variety of paths and tracks. Occasional uneven areas. Ascents/descents 1-2 hours. These trips are suitable for those who have a reasonable to good level of fitness.
Moderate to Challenging: walking along varied paths and surfaces, occasionally challenging, with ascents/descents of 2-3 hours. These trips are suitable for more experienced walkers who have a good level of fitness.
If you are planning to take an Independent trip as a single traveller, we would ask you to consider the potential dangers of walking alone before making a booking and if necessary discuss this with our Sales team.
Single travellers will be booked into a double room which will carry a single occupancy supplement.
Flights are not included in the price of your ATG holiday and should be booked independently.
The trips in our Independent programme make ideal family holidays for those with children who are old enough (and keen enough!) to enjoy a walking holiday or young enough to be carried in a backpack.
You would need to consider costs for lunches (either a picnic style lunch or lunch in a café as you prefer) and evening meals. Where an evening meal is included at a hotel this is indicated on the trip page. For evening meals not included, the route book provides restaurant recommendations to suit a wide range of budgets. You would also need to factor in any entrance fees to museums, churches, galleries and other sightseeing costs, items of a personal nature, shopping expenditure and transport if you choose to not to walk on some days.
Tourist Tax
This tax is charged per guest per night and the rate is determined by the local council based on the star rating of the accommodation. The rate usually varies from €2 up to €5 per person per night, although the rate can be higher in major cities. This tax is not included in the price of your holiday but where applicable will be payable direct to your hotel in cash.
We are delighted to book extensions for you at either end of your trip. We only book hotels with which we have an established relationship and where we can ensure a high level of service and enjoyment. If you would like an extension hotel booking please indicate this during the booking process and we will contact you with pricing information.
ATG does not provide any form of insurance cover. However, it is a condition of booking that you have fully comprehensive insurance cover, including:
Cancellation/curtailment up to the cost of the holiday (preferably including flights)
Medical emergencies and repatriation
Travel delay / missed departure
Lost or stolen personal belongings
Personal liability
Legal expenses
Natural Disasters
Although most credit card companies offer travel insurance as something that is included when paying the balance with the card, it may be advisable to check that the cover offered is what you expect it to be. Very few companies include cancellation and curtailment or medical expenses. Whatever the insurance policy you have taken out, please read the documentation carefully. Please ensure also that you take it with you on your trip and refer to it in the case of any claim or emergency.
Yes, please click here for what to bring. A packing checklist is also included with your booking confirmation.
Sustainability
ATG was founded on principles of conservation and sustainable development. It was the first company to win the tourism industry’s two top awards: Tourism for Tomorrow (UK) and the World Legacy Award (National Geographic and Conservation International USA) and also the first to have an accredited Environmental Management System.
Everyone who walks with ATG contributes to the ATG Trust, which funds projects that benefit local communities in the regions visited. By supporting these initiatives, ATG promotes sustainable tourism. Past projects have included heritage restoration projects, environmental conservation and educational projects.
Other trips you may be interested in
