Painting Tuscany – Escorted
Based at Pieve a Castello, ATG's 8th Century, historic monument set in unspoilt landscape in central 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.
A wonderful week combining tutored painting sessions in the glorious Tuscan countryside and at local sites of outstanding historic and cultural interest, excursions to delightful nearby towns and villages and optional walking.
The trip is led by David Walsh, a renowned artist working specializing in landscapes – and long-time ATG associate (www.david-walsh.net). Beginners are welcome!
Duration: 8 days
Trip dates:
02 - 09 Jun 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. Pre-dinner presentation of the tour leader's approach to the week.
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 painting session in the grounds of Pieve a Castello. After lunch, an optional afternoon walk explores the surrounding countryside (1-2 hours), before returning for afternoon tea. Time to relax - or paint - before dinner.
Aerial view of Pieve a Castello
We drive (10 mins) to a picturesque spot at the hamlet of nearby Abbadia Isola. After painting and visiting the abbey, we continue to hilltop Monteriggioni, a tiny medieval village. Late afternoon walk in the surrounding hills (1-2 hours). Dinner at a traditional local restaurant.
Abbadia Isola: Medieval village with 11C Benedictine Abbey, a key stopping place for pilgrims along the Via Francigena. Its 11C, Lombard church houses a 16C fresco by Vincenzo Tamagni and a 15C marble font originally from Pieve a Castello.
Monteriggioni: Beautifully sited and perfectly preserved village with 13th century walls, complete with 14 watchtowers and a small Romanesque church with a pretty façade.
One of the bedrooms
Morning painting session at a castle dating from the 13th century with Peruzzi gardens and wonderful views towards Monte Amiata. Optional afternoon walk.
Home to the aristocratic Aldobrandini family, the private castle and its well-tended gardens are in a spectacular setting, just 8 miles from Siena and with views of the city, but in tranquil countryside.
View of the courtyard at Pieve a Castello
We drive (20 mins) to a picturesque, frescoed church and hermitage for our morning painting session and enjoy wonderful views of Siena. Optional afternoon visit to nearby Casole, whose twinkling lights are visible at night from Pieve a Castello. Evening private concert in the church at Pieve.
Medieval hilltop village built on Etruscan foundations, with a wonderful views of the Sienese countryside. In the 11th and 12th centuries, the town was a fiefdom under the control of the Volterra Bishops, passing to Sienese control in 1260. Its strategic position meant it was perfectly situated to defend itself from external attacks, but also meant it subsequently needed to have new fortifications built, including two round towers that still stand, creating the village with its characteristic city walls.
Dinner in the Baptistry at Pieve a Castello
We drive (30 mins) to a viewpoint over classic Tuscan countryside. After our morning painting session we enjoy a picnic lunch with a view of medieval, iconic San Gimignano and its famous towers. Optional afternoon walk (1 hour) and visit to the town, or return to Pieve a Castello to paint or relax.
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, Museo Civico (Civic Museum, which includes a chance to climb the Torre Grossa, the city’s tallest tower) and Museum of Torture.
Picnic on the terrace at Pieve a Castello
Morning painting session. Optional afternoon visit to nearby Colle di Val d’Elsa, with its ancient walls and fascinating, medieval 'tunnel' streets. Optional late afternoon walk (1-2 hours), before a gala dinner.
Less crowded than the likes of San Gimignano and Siena, ‘Colle’ holds true to itself as a working town with an innovative people. The wool, paper and flour industries previously thrived here while today it is crystal and fine glass. Colle Alta, the quaint, upper part of the old town, perches on a narrow ridge and presents an impressive silhouette from below.
The courtyard at Pieve a Castello at night
Departure day.
Trip Planner
Walking & Terrain
Easy walking. This is an 8-day trip, with walks of 1-3 hours plus sightseeing. Hours of walking, which may vary from group to group, means hours of actual walking and does not include stops for lunch, sightseeing or rests.
The escorted walking is gentle, along established paths, dirt roads and woodland tracks. Please make sure that your footwear provides sufficient ankle support. We recommend you also bring lighter shoes for sightseeing. 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.
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.
For keener walkers, the gentle guided walks in the itinerary may freely be supplemented with self-guided walks at Pieve a Castello, where a wide selection of routes, with ATG ‘Footloose’-style walking directions (complete with measurements, maps, GPS coordinates and a wealth of other information) are available for anyone to enjoy.
Walking & Terrain
Easy walking. This is an 8-day trip, with walks of 1-3 hours plus sightseeing. Hours of walking, which may vary from group to group, means hours of actual walking and does not include stops for lunch, sightseeing or rests.
The escorted walking is gentle, along established paths, dirt roads and woodland tracks. Please make sure that your footwear provides sufficient ankle support. We recommend you also bring lighter shoes for sightseeing. 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.
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.
For keener walkers, the gentle guided walks in the itinerary may freely be supplemented with self-guided walks at Pieve a Castello, where a wide selection of routes, with ATG ‘Footloose’-style walking directions (complete with measurements, maps, GPS coordinates and a wealth of other information) are available for anyone to enjoy.
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 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 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 – most of the towns and villages in this area are built on Etruscan foundations. Roman colonisation occurred from the 2nd century BC. From the 12th century, many Tuscan cities prospered finding great wealth through new-found trades such as banking and wool. This led to the prominence of Siena, which became one of Europe’s greatest cities. During the 14th century, local family disputes and city rivalries resulted in the annexation of Sienese territories by Florence. Sienese towns and villages declined and have remained essentially preserved in their medieval state to the present day. The history of Pieve a Castello itself is very rich: you will learn more about this during your stay.
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.
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