Pieve a Castello: As You Like It (Itinerary 3) – Escorted
SAVE £250 per person on this Trip
(This will be deducted on receipt of your booking)
Walk back in time and explore one of the worlds most outstanding and iconic cultural hot-spots through 2,500 years of history - from Renaissance Florence and medieval Siena to Roman and ancient Etruscan Volterra.
This week’s selected highlights of the area include the spectacular ruined abbey of San Galgano and nearby church with the original ‘Sword in the Stone’ and Lorenzetti frescoes, delightful medieval Siena, a private Renaissance garden, and magnificent Volterra with its three miles of Etruscan walls.
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:
19 - 26 May 2026
26 May - 02 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. Evening presentation: 'The Via Francigena'.
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, following ancient routes of the Via Francigena, the early medieval 'main Road to Rome', through idyllic countryside to the Benedictine Abbey of Isola and the walled hilltop town of Monteriggioni. We return for lunch, and later enjoy a tour of the organic vegetable gardens, followed by a cooking demonstration. Evening presentation: 'The Medieval Traveller and the Legend of the Sword in the Stone’.
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.
Aerial view of Pieve a Castello
We drive (60 mins) to the village of Chiusdino and visit its small museum. We then walk to the spectacular, ruined Cistercian abbey of San Galgano and nearby small, domed Romanesque church – still with the 'Sword in the Stone’ (of San Galgano), from which the fable originates. Evening presentation: 'Contrada Tradition'.
A superb example of Cistercian Gothic architecture in open countryside, majestic in its abandoned splendour. Nearby is the equally remarkable Romanesque church of San Galgano, which contains the legendary ‘Sword in the Stone’ and frescoes by Ambrogio Lorenzetti.
One of the bedrooms
We spend the morning in Siena, where we visit lesser-known areas of ‘the best-preserved great medieval city in Europe’ and its ancient, but still vibrant ‘contrada culture’. Evening presentation: ‘Etruscan origins and legacy’.
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 (1 hour) across scenic hills, then walk to explore the great Etruscan city of Volterra, visiting Etruscan tombs, walls and gateways and the fine Etruscan museum. We return to Pieve a Castello (built on Etruscan foundations!) for an evening concert in the church.
Volterra is less visited than other Tuscan hilltop towns yet has so much to offer. A walled medieval city with a fine central piazza and cathedral. One of the largest and most important of the 12 Etruscan city states, it still features the remains of Etruscan walls, two Etruscan-Roman gateways, and circular tombs from the 6th century BC, as well as a well-preserved Roman theatre and baths. The Guarnacci Etruscan Museum is one of the best in Italy.
Dinner in the Baptistry at Pieve a Castello
We walk through the open country of the upper Elsa Valley before following paths up through olive groves to the medieval hill village of Casole d’Elsa – built on Etruscan foundations. Evening presentation: 'Chianti: Great Reds'.
Medieval hilltop village built on Etruscan foundations, with 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.
Picnic on the terrace at Pieve a Castello
We drive (20 mins) to Castello di Celsa – high in the Montagnola (wonderful views) and visit its fine 16th century gardens. There is a delightful (optional) walk part of the way back to Pieve a Castello. Evening: gala dinner.
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.
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.
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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