Chianti Hills: Siena to Florence – Escorted
We start in the magnificent medieval city of Siena, then walk out into the timeless landscapes of Tuscany, from rolling hills, vineyards and avenues of cypress trees surrounding Siena, moving into the high, forested hills of Chianti.
Along the way, pass through quiet medieval hill towns, some with wonderful frescoes, and wine estates with acres of Chianti vineyards. There is plenty of good food and local wine at every stop. The waysides are packed with wildflowers in spring, followed by poppies in May and June, fields full of bright yellow sunflowers in July, then delicate woodland cyclamen in the autumn.
The city of Florence, birthplace of the Renaissance, is the perfect conclusion to the trip. With an art gallery, important church or fine palazzo on every street, not to mention its elegant shops and restaurants, this is one of the most fascinating cities to visit in Europe.
Duration: 8 days
Trip dates:
25 Sep - 02 Oct 2026
Itinerary
NOTE: a FREE extra night in Florence is offered at the end of the tour. If you would like to take advantage of this, please let us know on booking. Your return to the airport would be on an independent basis. Day 1 itinerary: After arrival at Pisa or Florence airport we travel by road to Siena, where we stay at a hotel within the medieval city walls and walk through ancient streets to the famous central Piazza del Campo.
Siena is one of the most perfectly preserved medieval cities in Europe, with an abundance of outstanding 14th and 15th century art and architecture, from the famous Piazza del Campo, scene of the spectacular horse race ‘Il Palio’ contested by the historic ‘contrade’ into which the city is traditionally – and passionately! – divided, to galleries filled with iconic medieval masterpieces, and the great cathedral.
Large, modern hotel within the city walls
Follow tracks across hills with stone-walled olive groves, oak forest, and world-renowned Chianti Classico vineyards. (12.4 miles, 6 hours).
Villa in working wine estate with swimming pool
We walk through woods up to the fortified Romanesque church of San Polo-in-Rosso and follow farm tracks through high vineyards before descending through lichen encrusted woods to the vineyard covered hills around Gaiole-in-Chianti (7.5 miles, 4 hours).
Gaiole in Chianti is a scenic historic village in the Tuscany region of central Italy, located in the province of Siena, at the heart of the famous Chianti wine region. Surrounded by rolling hills, vineyards and olive groves, it also has medieval origins. The area is dotted with castles, Romanesque churches and wine estates such as Castello di Brolio, Badia a Coltibuono and Meleto Castle.
Medieval castle with swimming pools and Romanesque church
We walk to a fortified medieval village, then through extensive vineyards up to a ridge, descend into a valley, and continue past stone farmhouses and vineyards to Panzano, where we stay at a 4* villa with elegant garden lawns and pool (12.9 miles, 6 hours).
Characteristic hilltop village with medieval centre. Beautifully sited above the Conca d’Oro (Golden Valley) and overlooked by the remains of the 12th century castle and the church.
Converted patrician villa with outdoor pool and gardens
Free day, with optional short walk along hills with panoramic views over northern Chianti, before descending via a fine fortified stone village to the small town of Greve-in-Chianti, with its arcaded piazza and statue of the explorer Giovanni da Verrazzano (discovered Long Island), who was born nearby (5.8 miles, 2.5 hours).
A town devoted to Chianti wines. Many opportunities for tasting the best wines of the region. Some fine medieval buildings and arcaded piazza.
Converted patrician villa with outdoor pool and gardens
From Greve we walk up stone-walled lanes past olive groves and vineyards and follow woodland tracks through the forested Monti del Chianti, then emerge into a small fertile valley and climb to Strada-in-Chianti, where we stay. (14.7 miles, 8 hours).
Small town situated on the ancient Chiantigiana road on the northern edge of the Chianti Classico region.
Restored country villa with views, gardens and pool
We walk down to the Ema Valley, following the riverbank to the small town of Grassina, from where farm tracks, small country lanes and quiet roads lead to the famous Romanesque church of San Miniato al Monte, from where we descend by cypress-lined footpath into the heart of Florence. We cross the Ponte Vecchio and walk through city streets to our stylish 4* hotel, in a quiet piazza near the church of San Martino in Santa Maria della Scala (12.6 miles, 6.5 hours).
This magnificent city built on the banks of the Arno was the cradle of Renaissance of the arts in Italy under the aegis of the powerful ruling Medici family. Now, the world’s foremost ‘Art City’ with museums and art galleries galore, most notably the Uffizi. The Duomo (cathedral) and numerous churches across the city also house outstanding art and architecture. Together with its elegant shops and restaurants this is one of the most fascinating cities to visit in Europe.
Elegant hotel located in the historic centre
Return to Pisa or Florence airport. NOTE: This trip includes a FREE extra night in Florence. If you would like to take advantage of this, please let us know on booking. Your return to the airport would be on an independent basis.
Trip Planner
Walking & Terrain
Moderate to challenging walking. This is an 8-day trip with walks offered on 6 days. The length of each day varies from 2.5 to a maximum of 8 hours walking. ‘Hours of walking’ does not include stops for lunch, sightseeing or rests.
Around Siena the landscape is characteristic of central Tuscany: rolling hills, isolated farms and woodlands, arable land, olive groves, avenues of cypress trees, and historic hilltop towns. Further into Chianti there are high wooded hills, castles and fortified villages and, of course, vineyards. There are some reasonably tough ascents. The paths are farm and forest paths, gravel roads and some asphalt in and around towns. There are no vertiginous walks.
On certain days, the walk takes you into the hills where the paths cross a more rugged terrain — please make sure that your footwear provides sufficient ankle support. Some of our walks are very weather sensitive. If it is not possible to do a walk due to inclement weather, an alternative will be organised at the discretion of the Tour Leader.
Our support vehicles allow you the flexibility to walk 'as much or as little as you like', with drop-offs and pick-ups appropriate to the given day's itinerary. The Tour Leader will tell you each evening about the following day's walking options.
Walking & Terrain
Moderate to challenging walking. This is an 8-day trip with walks offered on 6 days. The length of each day varies from 2.5 to a maximum of 8 hours walking. ‘Hours of walking’ does not include stops for lunch, sightseeing or rests.
Around Siena the landscape is characteristic of central Tuscany: rolling hills, isolated farms and woodlands, arable land, olive groves, avenues of cypress trees, and historic hilltop towns. Further into Chianti there are high wooded hills, castles and fortified villages and, of course, vineyards. There are some reasonably tough ascents. The paths are farm and forest paths, gravel roads and some asphalt in and around towns. There are no vertiginous walks.
On certain days, the walk takes you into the hills where the paths cross a more rugged terrain — please make sure that your footwear provides sufficient ankle support. Some of our walks are very weather sensitive. If it is not possible to do a walk due to inclement weather, an alternative will be organised at the discretion of the Tour Leader.
Our support vehicles allow you the flexibility to walk 'as much or as little as you like', with drop-offs and pick-ups appropriate to the given day's itinerary. The Tour Leader will tell you each evening about the following day's walking options.
Your Personal ATG Route Manager
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
The hotels we stay in are characteristic of the area and the towns we visit.
There are some smart restaurants on this trip where a jacket would be appropriate, but not necessary. All evening meals are included and are taken either in the hotel or in local restaurants. At dinner, the Tour Manager will tell you about each evening’s menu and if there is anything else that you would prefer, you only have to ask.
Each day the Tour Manager will meet you with one of ATG’s celebrated picnic lunches. You will be greeted with mineral water and a starter followed by wine and an abundant lunch of local organic produce and specialities. Picnics are colourful, varied and nutritious. Buffet-style, there is a choice of meats, cheeses, substantial salads, bread and fruit…and pudding. If it is cold there will be a hot dish.
Food & Wine
Tuscan food is simple and uses good local ingredients. Although the Tuscans are called ‘bean eaters’ (mangiafagioli) the main staple of their diet, apart from pasta, is bread which is traditionally unsalted to complement the salted prosciutto, salami and strong sheep’s cheeses. Whilst it is a traditional cuisine, it is not a poor one, and meat and game feature strongly, preferably cooked on an open fire. The Tuscans are less interested in the presentation of the food than in the excellence of the ingredients, and even the most elegant restaurants serve rustic terracotta bowls of rich vegetable and bean soups. The Tuscans also have a sweet tooth, producing a variety of rich spicy cakes full of candied fruit and nuts, and light biscuits. During the course of the trip you will be walking through the vineyards of Italy’s most famous wine, Chianti. Both Chianti Classico and Chianti Colli Senesi come from small, strictly delineated areas, two of the seven regions within Chianti. Alongside the more ‘serious’ Chianti Riserva are produced other, less expensive ‘quaffing’ Chianti made to be drunk within a year or so of production — an excellent accompaniment to local dishes.
History
Most of the towns and villages along our route are built on Etruscan foundations. Roman colonisation occurred from the 2nd century BC. Wealth in the Middle Ages, from trades such as banking and wool, led to the prominence of Siena, which became one of Europe’s greatest cities. During the 14th century Guelph-Ghibelline disputes resulted in the annexation of Sienese territories by Florence. Sienese towns and villages declined and have remained preserved in their medieval state to the present day.
Frequently Asked Questions
Escorted trips are accompanied by two of ATG’s fully trained Tour Consultants, from the moment they welcome you at the airport, through to the end-of trip airport transfer. The Tour Manager looks after the practical side of the trip – luggage transport, hotels, food and drink. The Tour Leader will lead each day’s walk, and after dinner each evening will tell you about the following day’s itinerary. Both Tour Consultants will explain their role, and how the trip will run, on the first evening at dinner.
Please let us know about any dietary restrictions or allergies in advance so that our Tour Consultants can ensure that you are catered for during your holiday. Most dietary restrictions do not present a problem on our trips and the Tour 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.
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. We will advise you of the group meeting time at the destination airport and return transfer time to the airport at the end of your trip to enable you to book compatible flights.
Yes. All of our escorted trips can be booked privately, you can book a set departure or a date to suit you (subject to availability). In most instances if the group is 13-16 clients we will offer the trip at the published price. For 12 or fewer clients we would provide a bespoke costing.
On escorted trips everything is included (per the published itinerary) apart from items of a personal nature and snacks or drinks outside of the set meals.
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 Tour Leader 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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