Pieve a Castello: As You Like It (Itinerary 1) – Escorted
Discover the beauty and incomparable wealth of World Heritage sites between the great Art cities of renaissance Florence and medieval Siena in central Tuscany.
This week’s selected highlights of the area include visits to tiny iconic Monteriggioni with its 14 watchtowers, the Abbeys of Isola and Sant’Antimo, built of alabaster and onyx, a private fine Renaissance garden, Siena and frescoes of Ambrogio Lorenzetti, and Florence with San Miniato al Monte before returning to idyllic Pieve a Castello to relax before another memorable evening and dinner.
At Pieve, a unique Rezidenza d’Epoca, you can relax and enjoy being guests in a private residence with 2 experienced members of the ATG Team to coordinate hospitality arrangements, provide expert knowledge of the area and guide each day of the itinerary – or for those who decide ‘opt-out’, to just enjoy the facilities of this very exceptional place.
Duration: 8 days
Trip dates:
28 Apr - 05 May 2026
09 - 16 Jun 2026
01 - 08 Sep 2026
15 - 22 Sep 2026
13 - 20 Oct 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: 'Tuscan heritage'.
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 idyllic countryside to discover paths and tracks – once routes of the ancient ‘main road to Rome’. We return for lunch and later enjoy a tour of the organic vegetable gardens, followed by a cooking demonstration. Evening presentation: 'Dante Alighieri, Guelfs and Ghibellines'.
Aerial view of Pieve a Castello
We drive (25 minutes) to Villa Vicobello, and visit the fine Renaissance garden built by Baldassare Peruzzi for the Chigi family in the 16th century. After returning for lunch there is the option of a walk following the ancient Via Francigena to a frescoed church and hermitage. Evening presentation: ‘Good and Bad Government by Ambrogio Lorenzetti'.
Built for the Chigi family in the 16th century (and owned by the family ever since) this fine villa with terraced gardens is attributed to Baldassare Peruzzi, architect of many notable villas and gardens around Siena.
One of the bedrooms
We spend the morning in Siena, visiting the Palazzo Pubblico and enjoying iconic, early Renaissance works of art including the Lorenzetti's renowned frescoes. Optional free afternoon to explore the city. Evening presentation: ‘Ascendancy of the Medici’.
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.
View of the courtyard at Pieve a Castello
We drive (45 mins) to hills overlooking Florence and walk to visit the magnificent church of San Miniato al Monte, before exploring other nearby ‘gems’. Evening concert in the church before dinner.
Arguably the finest Romanesque building in Tuscany, San Miniato is also the oldest surviving church in Florence after the Baptistery, and stands atop one of the highest points in the city.
Dinner in the Baptistry at Pieve a Castello
We drive (1 hour 10) to Montalcino, south of Siena, centre of the famous Brunello wine producing area, then walk through vineyards to the exquisite Abbey church of Sant’ Antimo, built out of alabaster and onyx. Evening presentation and wine tasting: 'Chianti!'
Inhabited since Etruscan times, this little medieval town boasts a spectacular location and a splendid fortress. It is the home of one of Italy’s most famous wines – Brunello di Montalcino. Its sacred art museum is also very highly rated by all who visit.
Picnic on the terrace at Pieve a Castello
We walk through the forests of the Montagnola, following early medieval paths, to the fortified, hilltop village of Monteriggioni with its 14 watch towers, described in Dante’s ‘Divine Comedy’. Evening: gala dinner.
A beautifully sited and perfectly preserved village encased within 13th century walls, complete with watchtowers. In the main square is a small Romanesque church with a pretty façade.
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 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 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. Most of the towns and villages in this area 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 essentially 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 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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