Paths of Chianti: Siena to Florence – Independent
Travel between two of the great art capitals in the western world with over 60% of the greatest works of art in the western world.
You'll start in the medieval city of Siena, then traverse the high, forested hills of Chianti, to Florence, birthplace of the Renaissance. Passing through medieval hilltop towns, fortified villages and, of course, the many acres of vineyards that cloak the Chianti hills. Expect plenty of excellent food and wine along the way, many of the villages visited have a selection of shops for tasting and buying wines as do the wine estates you'll pass on route.
Spring is prime time for flowers and birds and late September is the time to see the vendemmia, or grape harvest, in action.
Duration: 8 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. Stay in a modern 4-star hotel within the city walls.
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 small museums. This is notably the home of the world-famous, spectacular bareback horse race Il Palio, run on 2 July and 16 August.
Modern hotel within the city walls
Follow tracks across hills with stone-walled olive groves, oak forest and world-renowned Chianti Classico vineyards to your accommodation in Dievole, a working wine estate with pool (12.7 miles, 6.5 hours).
Set within the Chianti Classico hills, this elegant wine resort is the perfect place to unwind. Stroll through the gardens, olive groves and vineyards of the estate, cool off in the pool and, of course, take a tour of the property and sample the wine and olive oil that they produce.
Villa in working wine estate with swimming pool
Upgrade option is a deluxe room
Cross a valley to the fortified Romanesque church of San Polo in Rosso, where paths lead to Gaiole-in-Chianti, a centre of Chianti wine production, overlooked by the Castello di Spaltenna and its 11th century Romanesque church (7.2 miles, 4 hours). Family-run B&B or upgrade to luxury accommodation in a restored medieval castle.
An important marketplace since the Middle Ages, Gaiole is overlooked by the Castello di Spaltenna and its 12th century Romanesque church. This is a good place for sampling Chianti Classico – visit Badia a Coltibuono. This Vallambrosan abbey was founded in the 11th century and there are records of monks planting vineyards here back in 1080, making it one of the most historic wine estates in the Chianti region.
Family-run B+B in town centre
Medieval castle with swimming pools and Romanesque church
Farm roads (strade bianche) lead to a ridge, from where a track descends to the valley, continuing past stone farmhouses and vineyards to a second ridge with extensive views, and the characteristic medieval hill town of Panzano (12.6 miles, 7 hours). 3-star farmhouse stay with pool or upgrade to a 4-star villa with pool and gardens.
Characteristic hilltop village with medieval centre. Nearby (close to Hotel Villa Le Barone) is the Romanesque Pieve di S. Leolino, with a fine 13th century Madonna with Saints. From here you could take the optional walk to Greve-in-Chianti, a town devoted to Chianti wines. There are many opportunities for wine tastings here as well as visiting some fine medieval buildings and the Museum of Sacred Art.
Converted farmhouse with outdoor pool
Patrician villa with pool, gardens and tennis court
Visit the small church of Pieve di San Leolino in Panzano, restored by the ATG Trust. Short optional walk to Greve-in-Chianti, a busy centre of the wine industry, with some fine medieval buildings and arcaded central piazza (5.8 miles, 3 hours).
Converted farmhouse with outdoor pool
Patrician villa with pool, gardens and tennis court
Undulating paths and strade bianche with fine views across vine-filled valleys and castles protecting the rich wine estates. A wooded riverside path then leads to the final climb to Impruneta (18.3 miles, 9.5 hours) and your 3-star central hotel, or upgrade to a wine resort stay in the countryside just outside Impruneta. Option to shorten the walk by getting a lift part way or starting from Greve (12.1 miles, 6 hours).
A town situated among the forested slopes of the Chianti hills, best known for its 11th century church of Santa Maria and its history of high-quality terracotta production. Visit the small kiln of Mario Mariani, identical to those used during Roman times. He uses traditional techniques to make terracotta pots and carry out restoration work.
Friendly, family-run hotel in town centre
Wine resort with pool and lovely gardens
Tracks and strade bianche lead through farmland to the outskirts of Florence. Walk along minor roads and pathways for the final two miles, then emerge at a panoramic view of the city and descend to the Ponte Vecchio. ‘Birthplace of the Renaissance’ and with the Uffizi, Pitti galleries, cathedral, churches and museums, Florence is the world’s greatest ‘Art City’ (10 miles, 5.5 hours). Stay in a 3-star historic hotel just outside the city centre or upgrade to an elegant 4-star hotel within the heart of the city.
Florence is the world’s foremost ‘Art City’ with museums and art galleries galore, most notably the Uffizi, containing the world’s greatest collection of Italian Renaissance painting. The Duomo (cathedral) and numerous churches across the city also house outstanding art and architecture. There is also an exceptional variety of shops, bars and restaurants. Our Route Book provides a handy guide to our top pick of sights, boutiques and eateries.
Family-run hotel in historic building, a short walk from city centre
Breathtakingly central location!
Trip Planner
Walking & Terrain
Walking: Moderate to challenging. The walk is through hills so expect some reasonably tough climbs on certain days. The length of walks vary from 2.5 hours to a maximum 9 hours.
Hours of walking, which may vary from individual to individual, means hours of actual walking and does not include stops for lunch, sightseeing, rests or siestas.
Terrain: The hiking is in forested limestone hills. There are some reasonably tough ascents. The paths are farm and forest paths, strade bianche (small gravel roads) and some surfaced roads in and around towns. On certain days the paths cross more rugged terrain – 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. The walk is through hills so expect some reasonably tough climbs on certain days. The length of walks vary from 2.5 hours to a maximum 9 hours.
Hours of walking, which may vary from individual to individual, means hours of actual walking and does not include stops for lunch, sightseeing, rests or siestas.
Terrain: The hiking is in forested limestone hills. There are some reasonably tough ascents. The paths are farm and forest paths, strade bianche (small gravel roads) and some surfaced roads in and around towns. On certain days the paths cross more rugged terrain – 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.
Art & Architecture - we’d recommend more time in Siena and Florence to enjoy all that these cities can offer and ATG offers self-guided city walks to take in the highlights of both Siena and Florence.
Wine Tasting at Villa Dievole – this is a free tasting offered late afternoon by the wine estate and can include a visit to the wine cellar. Olive oil tasting also available.
Cooking Class at Fattoria Valle, Panzano in Chianti. Costs 100€/person (including dinner but excluding drinks)
Additional Walking in Gaiole in Chianti – option to do a walk to the wine estate of Badia a Coltibuona a and enjoy a lunch and wine tasting there.
Your Personal ATG Route Manager
I was born in Romania but have lived in Florence since 1998. Since then I have travelled all over Italy but, for me, Tuscany has it all – the marvellous art and architecture of the cities, the wonderful landscapes, profound peace, and delicious food and wine. I have worked for ATG since 2012 and absolutely love helping people get the most out of their holiday to this beautiful region.
“Maria (Route Manager) was friendly, professional, pro-active and helpful”
“Maria's enthusiasm, knowledge and professionalism enhanced our experience. She went out of her way to help us make the most of our time in Chianti.”
“She (Route Manager) was very helpful and informative. I was also very pleased with her help with dining recommendations and reservations.”
“Maria (Route Manager) was wonderful! Very helpful when my injury messed up the walks. Could not have been more helpful or accommodating.”
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 wines of the region. You will be walking through the vineyards of Italy’s most famous wine, Chianti. You may also like to try Vernaccia, a white wine for which nearby San Gimignano is famous, and the delicious local dessert wine, Vin Santo. Many of the villages visited en route have a selection of shops for tasting and buying wines, while the wine estates you pass offer sampling and direct sales. 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, particularly in the Spring. 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. 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.
Return travel from Florence:
For Pisa airport, there are regular, direct trains to Pisa Centrale, where you need to change onto the PisaMover shuttle to the airport.
For Florence airport, simply take the tram line from the city centre.
For Rome Fiumicino airport, take the train to Roma Termini to connect with the Leonardo Express shuttle to the airport.
Trip Options & Prices
Overview
This 8 day independent walking tour in Tuscany includes 5 days walking plus 1 optional walk. Enjoy this weeklong trip in Italy as you pass through the famous Chianti countryside with its medieval hilltop villages and vineyards, between the two great art cities of Siena and Florence.
Itinerary
Day 1: Arrive in Siena
Day 2: Siena to Dievole*
Day 3: Dievole to Gaiole-in-Chianti*
Day 4: Gaiole-in-Chianti to Panzano*
Day 5: Panzano* - free day
Day 6: Panzano to Impruneta (via Greve-in-Chianti)*
Day 7: Impruneta to Florence*
Day 8: 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.
Your Route Manager will be able to tell you about the ATG Trust project on this route involving the restoration of the 15th Century Polyptych by Mariotto di Nardo, located in the apse of the church of San Leolino.
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