Siena and the Palio – Escorted
Il Palio, the famous horse race around the Piazza del Campo in Siena, is one of the of the world’s great spectacles – colourful, dramatic and steeped in centuries of tradition – and set against the back-drop of Europe’s best-preserved great medieval city.
To ensure the fullest experience of this quintessentially Italian festival, we make the brief journey into Siena several times to learn about the city and its way of life. We follow the process of the Palio from the allocation of horses, to the prove (trials), the pre-race dinner, and finally experience for ourselves the intense excitement of the race itself, which (whilst enjoying champagne and canapés!) we view from the window of a palazzo overlooking the Piazza del Campo.
The week also includes gentle walking and visits to medieval San Gimignano and Monteriggioni, with time to relax and enjoy the surroundings at Pieve a Castello.
Duration: 8 days
Trip dates:
27 Jun - 04 Jul 2026
Itinerary
After arrival at Pieve a Castello and time to relax, there will be a tour of this unique complex of early 8th century buildings. Evening presentation: ‘The Palio: its history and traditions’.
Pieve a Castello is built around the courtyard of a subsequently demolished castle and is today flanked by a basilica-style proto-Romanesque church, an octagonal baptistery, a three storey casa colonica and some single-storey buildings. These were used in medieval times for accommodating travellers from the nearby Via Francigena (the medieval road to Rome), as accommodation for monks, and, later, as living quarters for farm workers.
View of the pool at Pieve a Castello
Morning visit, with a range of walking options (10 minutes to 3 hours), to the nearby, walled, hilltop village of Monteriggioni, with its 14 watchtowers. Evening presentation: ‘Siena: The Antechamber of Paradise’.
A beautifully sited and perfectly preserved village with 13th century walls, complete with watchtowers. In the main square is a small Romanesque church with a pretty façade.
Aerial view of Pieve a Castello
Morning visit to Siena to watch the tense ‘draw’ in which Palio horses are allotted to the competing contrade. After lunch at a restaurant in the medieval city, there are opportunities for further exploration of Siena or to walk historic paths through the forested Montagnola back to Pieve a Castello. Evening presentation: ‘Via Francigena’.
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 to galleries filled with iconic medieval masterpieces, and the great cathedral.
One of the bedrooms
Morning visit to iconic San Gimignano, ‘the Medieval Manhattan’, with a brief, optional scenic approach on foot and a range of walking options. Lunch at Pieve a Castello. Evening presentation: ‘Palio di Provenzana’.
The ‘city of the towers’ is irresistibly charming and perfectly preserved. Highlights include the Collegiata (former cathedral) with wonderful frescoes, the Museum of Modern Art and Museo Civico (Civic Museum).
View of the courtyard at Pieve a Castello
We visit Siena in the late afternoon to see the 'Prova Generale' – the final practice race in the Piazza del Campo, which we watch from the palazzo windows, before joining one of the contrade as guests at their pre-Palio dinner.
Held in honour of the Virgin twice yearly on 2 July and 16 August – the former began in the 17th century, the latter in 1147. The horses are drawn by lots, but jockeys are chosen by individual contrade. Because of the narrowness of the track (three times around the Campo) only 10 contrade compete – again drawn by lots. Several days before the race there are a series of ‘prove’ – tests in which the horses run around the track.
The courtyard at Pieve a Castello at night
The day of the Palio! Afternoon visit to Siena to see the colourful medieval pageant and watch the Palio horse race from the windows of an ideally situated palazzo, followed by dinner at a restaurant in the medieval city.
While the race only lasts a few minutes (although the start can take an hour) there is a magnificent procession beforehand of all the 'contrade' in wonderful medieval costumes with flag throwing. We strongly recommend you bring binoculars.
Picnic on the terrace at Pieve a Castello
Day to relax at Pieve a Castello. Evening concert in the church, followed by a gala dinner.
Dinner in the Baptistry at Pieve a Castello
Departure day.
Trip Planner
This is an 8-day holiday, with optional walks of 2-3 hours in length offered on 3 days, plus sightseeing. The walking is gentle, along established paths across the Tuscan hills, dirt roads and woodland tracks, some of which may be stony. Please make sure that your footwear provides sufficient ankle support and walking poles may be useful. We recommend you also bring lighter shoes for sightseeing.
The area we visit is the central part of Tuscany — a landscape characterised by medieval hilltop villages and scattered cypress trees, undulating vineyards and olive groves. Its gently rolling hills are disarmingly familiar as the classical backdrop of Renaissance art and its charm is a changelessness, which merges medieval and modern worlds.
Some of our walks are weather sensitive. If it is not possible to do a walk due to inclement weather, an alternative will be organised. Any such decision is at the discretion of the Tour Leader.
For keener walkers, some further 200 miles of researched walks around Pieve — with ATG ‘Footloose’-style walking directions and measurements, maps and GPS coordinates, and a wealth of other information-are available to our guests at Pieve.
This is an 8-day holiday, with optional walks of 2-3 hours in length offered on 3 days, plus sightseeing. The walking is gentle, along established paths across the Tuscan hills, dirt roads and woodland tracks, some of which may be stony. Please make sure that your footwear provides sufficient ankle support and walking poles may be useful. We recommend you also bring lighter shoes for sightseeing.
The area we visit is the central part of Tuscany — a landscape characterised by medieval hilltop villages and scattered cypress trees, undulating vineyards and olive groves. Its gently rolling hills are disarmingly familiar as the classical backdrop of Renaissance art and its charm is a changelessness, which merges medieval and modern worlds.
Some of our walks are weather sensitive. If it is not possible to do a walk due to inclement weather, an alternative will be organised. Any such decision is at the discretion of the Tour Leader.
For keener walkers, some further 200 miles of researched walks around Pieve — with ATG ‘Footloose’-style walking directions and measurements, maps and GPS coordinates, and a wealth of other information-are available to our guests at Pieve.
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
This trip is based at Pieve a Castello for the week. There are 10 bedrooms originally used for multiple-occupancy by medieval travellers. In a protected building of this antiquity, every room is different, each with unique features and all with views of the central courtyard and open countryside. Please let us know any room preferences when you book, which we will confirm subject to availability.
All evening meals are included and Pieve a Castello has a resident chef who combines first-class ingredients, including the organic produce from his vegetable and herb gardens at Pieve a Castello to produce delicious and elegant dishes that showcase the best traditions of Tuscan cookery.
A three-course dinner is preceded by pre-dinner drinks and canapés, served in the library or its adjacent terrace (the ‘sunset terrace’).
Each day the Tour Manager will prepare one of ATG’s celebrated picnic lunches, often served on one of the terraces at Pieve a Castello. 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.
Room 1: Large, first-floor room with writing room, bath-shower (double/twin)
Room 3: Large, second-floor room with unique shower room (double/twin)
Room 5: Former dovecote on second floor with spacious shower (double)
Room 8: Courtyard room with bath-shower and side door to garden (double/twin)
Room 10: Cosy courtyard room with shower (single room with single bed with no single room supplement)
Room 2: Large, second-floor room with writing room, bath-shower (double/twin)
Room 4: ‘Cosy’ room on second floor with four-poster bed, bath-shower (double)
Room 7: Courtyard room with bath-shower and side door to garden (double/twin)
Room 9: Charming, corner courtyard room with shower (single room, French-sized double bed with no single room supplement)
Room 11: Courtyard room – with writing niche, shower and 8th-century apse (!) (double)
Food & Wine:
Tuscan food is simple and uses good local ingredients which complement the excellent robust wines of the region. It is seasonal food usually prepared with home grown 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 also have a sweet tooth, producing a variety of rich spicy cakes full of candied fruit and nuts, and light biscuits. The local cheese is predominantly pecorino (a sheep’s cheese: ‘pecora’ means ‘sheep’) enjoyed at varying stages of maturity.
During the course of your holiday you will see – and probably walk through – the vineyards of Italy’s most famous wine, Chianti. Known originally in England as ‘Florence Red’, the wine gained renown in the 19th century, when Barone Ricasoli (Italy’s second Prime Minister) developed the grape composition found in today’s wines. Chianti now occupies a large area of hills to the south (and east) of Florence, and Pieve a Castello is located in the designated Chianti zone called Colli Senesi (Sienese Hills), one of 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. To the south of Siena, there are other superb local red wines, notably Brunello di Montalcino and Vino Nobile di Montepulciano, which, with their full-bodied character and strong tannins, complement Tuscan cuisine very well. The less aged red of Montalcino is also very good indeed. You may have the opportunity to try other excellent Tuscan wines including Vernaccia, the white wine for which nearby San Gimignano is famous, the delicious wines from Bolgheri in the coastal province of Livorno, as well as the delicious Tuscan ‘passito’ dessert wine, Vin Santo.
History:
The Palio is held in Siena in honour of the Virgin twice yearly on 2 July and 16 August – the former began in the 17th century, the latter in 1147. The horses are drawn by lots, but jockeys are chosen by individual contrade. Because of the narrowness of the track (three times around the Campo) only 10 contrade compete – again drawn by lots. Several days before the race there are a series of ‘prove’ – tests in which the horses run around the track. This is primarily for the animals to become used to the conditions and crowds, but the locals watch keenly to assess the horses. The race is run bareback and every trick is used to win. Indeed, the word ‘jockey’ is a dirty one in Italian! Even a rider-less horse can win and is thought to be very lucky! While the race only lasts a few minutes (although the start can take an hour) there is a magnificent procession beforehand of all the contrade in wonderful medieval costumes with flag throwing. We strongly recommend you bring binoculars.
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 at Monteriggioni, a tiny medieval village near Pieve a Castello, involving the restoration of the Porta Romea. This restoration formed part of a much larger project to restore the walls around the village of Monteriggioni. The Porta Romea is the gateway facing Rome through which many ATG clients will have walked.
Other trips you may be interested in
