Tuscan Food & Wine – Escorted
Over a week at Pieve a Castello, guests will enjoy historical tours, culinary demonstrations, and wine tastings. From walks through vineyards to hands-on experiences like preparing antipasti cooked on hot stones, each day offers immersion in Tuscan traditions. Cooking demonstrations cover everything from simple dishes to creative uses of local ingredients, accompanied by presentations on the region's gastronomic evolution.
Walks include visits to prestigious wineries in Chianti Classico and San Gimignano, where guests taste wines such as Vernaccia and Colli Senesi. Special dinners and unique events, like a private concert in a historic church, enrich the experience. The week concludes with a morning stroll in Siena and an evening talk on dessert wines and grappa, leaving an authentic and multisensory memory of Tuscany.
Duration: 8 days
Trip dates:
21 - 28 Apr 2026
16 - 23 Jun 2026
10 - 17 Nov 2026
Itinerary
After arrival at Pieve a Castello there will be a tour of this unique complex of 8th Century buildings, and produce in the organic vegetable gardens. Evening presentation: ‘Evolution of Tuscan Food and Wine’
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
We walk through vineyards to visit a producer of 'Colli Senesi' wines. Cookery demonstration: ‘Simple Beginnings’. In addition, guests are invited to make an antipasto at dinner, cooked at the table on hot stones.
Aerial view of Pieve a Castello
We drive into the hills to walk and visit one of the most prestigious wine estates outside the ‘Chianti Classico’. Cookery demonstration: ‘What’s in la dispensa?'
View of the courtyard at Pieve a Castello
After a short transfer, we walk and enjoy views of iconic San Gimignano, then visit a notable wine estate producing 'Vernacia di San Gimignano'. Cookery demonstration: ‘Tuscan fish'
The ‘city of the towers’ is irresistibly charming and perfectly preserved, and surrounded by iconic Tuscan countryside of vineyards, olive groves and cypress trees.
One of the bedrooms
We drive to the ‘Chianti Classico’ to walk in an picturesque area and visit an estate producing a range of wines – from traditional to innovative. In the evening we enjoy a private concert in the church before dinner. Cookery demonstration: ‘Tuscan free range'
Picnic on the terrace at Pieve a Castello
We drive to Siena for a Sunday morning 'passegiata'. Cookery demonstration: ‘Wild and wonderful: sustainable quality’. Evening presentation: ‘Dessert wines - digestivi & grappa’
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.
Dinner in the Baptistry at Pieve a Castello
We visit one of the most renowned wine estates in Chianti Classico. Cookery Demonstration ‘Make a gift to take home’. Evening Presentation: ‘So, why does it taste so good?’.
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 across the Tuscan hills, dirt roads and woodland tracks. 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 across the Tuscan hills, dirt roads and woodland tracks. 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 fundamentally quite 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 baked 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 simply over an open fire. The Tuscans also have a sweet tooth, and produce a variety of rich spicy cakes full of candied fruit and nuts, and crunchy 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. 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 Rosso of Montalcino is also very good indeed. You may also have the opportunity to try other excellent Tuscan wines including Vernaccia, the white wine for which 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
Roman colonisation of the area began in the 2nd century BC. Wealth in the Middle Ages led to the prominence of Siena which became one of the greatest cities of Europe, but the 14th century Guelph-Ghibelline disputes resulted in the annexation of Sienese territories by Florence. Sienese towns and villages declined and remained almost unchanged to the present day — perfectly preserved in their medieval state.
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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