Telephone +44 (0) 1865 315 678 | trip-enquiry@atg-oxford.com

Pieve a Castello: As You Like It (Itinerary 2) – Escorted

SAVE 10% per person on 14th April departure + SAVE £250 per person on all other departures

(This will be deducted on receipt of your booking)

Discover the beauty and incomparable wealth of World Heritage sites between the great Art cities of renaissance Florence and medieval Siena in central Tuscany.

The weeks selected highlights of the area include visits to  ‘discover’ nearby Colle Val d’Elsa with its tunnel streets and ancient mills, delightful medieval Siena, the superb Abbey of Monte Oliveto Maggiore with its frescoed cloister and iconic San Gimignano before returning to the welcoming tranquillity and comfort of ancient Pieve a Castello and another relaxed evening and memorable 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

Price: £3,640 per person

Trip dates:

14 - 21 Apr 2026
08 - 15 Sep 2026 - No longer available
22 - 29 Sep 2026
20 - 27 Oct 2026

Trip Type: Escorted
Country: Italy
Airport: Pisa & Florence
Grade: Easy Walking
Walk Length: 1 / 3 hours

Itinerary

Day 1

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 Augustinian Canonry'.

The courtyard at Pieve a Castello walking tour Tuscany Italy
The courtyard at Pieve a Castello
About Pieve a Castello

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 Pieve a Castello and the pool Escorted walking tour Tuscany Italy
Near Monteriggioni
Pieve a Castello

View of the pool at Pieve a Castello

We walk, following routes used by early medieval travellers between Pieve a Castello’s 22 small, dependent canonries. We return for lunch and later enjoy a tour of the organic vegetable gardens, followed by a cooking demonstration. Evening presentation: 'Renewable medieval energy'.

Aerial view of Pieve a Castello and surrounding landscape Escorted walking tour Tuscany Italy
Aerial view of Pieve a Castello and surrounding landscape
Aerial view of Pieve a Castello Escorted walking tour Tuscany Italy
Near Monteriggioni
Pieve a Castello

Aerial view of Pieve a Castello

 

We walk from Pieve a Castello following ancient tracks to nearby Colle Val d’Elsa where we visit the fortified, medieval ‘Colle Alta’ and its tunnel streets, and lower town with ‘le gore’ – an ancient water system powering this ‘town of mills’. Evening presentation: 'The Anti-chamber of Paradise'.

View of Colle di Val d'Elsa walking tour Tuscany Italy
View of Colle di Val d'Elsa
About Colle Val d’Elsa

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.

One of the bedrooms at Pieve a Castello Escorted walking tour Tuscany Italy
Near Monteriggioni
Pieve a Castello

One of the bedrooms

We walk through the forests of the Montagnola to a frescoed church and hermitage. After lunch we visit Siena to discover the history and outstanding art and architecture of the Cathedral complex. Evening presentation: ‘Wealth created by the Via Francigena’.

View of Siena walking tour Tuscany Italy
View of Siena
About Siena

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 Escorted walking tour Tuscany Italy
Near Monteriggioni
Pieve a Castello

View of the courtyard at Pieve a Castello

We drive (20 mins), then walk up a track with panoramic views of San Gimignano, the ‘medieval Manhattan', surrounded by olive groves and vineyards. After walking through the town, we continue down into the scenic hills to the Elsa Valley to visit the fortified village of Certaldo, birthplace of Boccaccio. We return to Pieve a Castello for a concert in the church before dinner.

View of San Gimignano walking tour Tuscany Italy
View of San Gimignano
About San Gimignano and Certaldo

San Gimignano 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).

Certaldo  A classic Tuscan hilltop village with Etruscan roots and medieval town steeped in history, culture and art, once a prominent stop on the Via Francigena.

Dinner in the Baptistry at Pieve a Castello Escorted walking tour Tuscany Italy
Near Monteriggioni
Pieve a Castello

Dinner in the Baptistry at Pieve a Castello

We drive (1 hour) to visit the great Benedictine abbey of Monte Oliveto Maggiore, where, amongst other delights, is a cloister with frescoes by Signorelli and Sodoma. We walk through the surrounding landscape of picturesquely eroded hills. Evening presentation and wine tasting: 'Chianti!'

Cloister at Monte Oliveto maggiore walking tour Tuscany Italy
Cloister at Monte Oliveto Maggiore
About Monte Oliveto Maggiore

A 14th century, red brick, Benedictine monastery in the unique ‘crete’ landscape. Tuscany’s ‘grandest’ monastery, renowned for its wealth of Renaissance frescoes.

Picnic on the terrace at Pieve a Castello Escorted walking tour Tuscany Italy
Near Monteriggioni
Pieve a Castello

Picnic on the terrace at Pieve a Castello

We drive (35 mins) to visit Villa Geggiano, just outside Siena, with its elegant gardens, theatre and wonderful views over the city. Afternoon at leisure. Evening: gala dinner.

Villa di Geggiano Escorted walking tour Tuscany Italy
Villa di Geggiano
About Villa di Geggiano

Originally built in the 14th century and renovated around 1780, the Villa di Geggiano and its winery have been home to the Bianchi Bandinelli family since 1527. Declared a National Heritage site, it contains its original decorations and furnishings. In the gardens is an open-air theatre which hosts classical music concerts in the summer.

View of the courtyard at night Escorted walking tour Tuscany Italy
Near Monteriggioni
Pieve a Castello

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.Boots

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.

 

ATG Trust logo

Other trips you may be interested in

Scroll to Top

Book this Trip

Pieve a Castello: As You Like It (Itinerary 2) – Escorted


Select room type

Lead Passenger Details

Address
This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.
Walkers heading towards Madonie mountains Escorted walking tour Sicily Italy

Special Offers 2026!

Thinking of a Spring or early Summer getaway? 
See Latest News for ATG walking tours departing this Spring & early Summer and take advantage of offers of £250 per person off all Escorted tours  (or more for certain trips) and £125 per person off many of our Footloose Independent tours plus FREE taxi transfer to reach selected Independent tours in Portugal and Spain.