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Pieve a Castello: As You Like It (Itinerary 1) – Escorted

SAVE £250 per person on this Trip

(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.

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

Price: £3,640 per person

Trip dates:

28 Apr - 05 May 2026 - No longer available
09 - 16 Jun 2026
01 - 08 Sep 2026 - No longer available
15 - 22 Sep 2026
13 - 20 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: 'Tuscan heritage'.

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 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'.

Walkers near Pieve a Castello walking tour Tuscany Italy
Walkers near Pieve a Castello
Aerial view of Pieve a Castello Escorted walking tour Tuscany Italy
Near Monteriggioni
Pieve a Castello

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'.

Gardens at Villa Vico Bello Escorted walking tour Tuscany Italy
Gardens at Villa Vico Bello
About Villa Vicobello

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 at Pieve a Castello Escorted walking tour Tuscany Italy
Near Monteriggioni
Pieve a Castello

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’.

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 (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.

Florence view walking tour Tuscany Italy
Florence view (photo: Christopher Whinney)
About San Miniato al Monte

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 Escorted walking tour Tuscany Italy
Near Monteriggioni
Pieve a Castello

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!'

Sant Antimo walking tour Tuscany Italy
Romanesque abbey-church of Sant’Antimo
About Montalcino

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 Escorted walking tour Tuscany Italy
Near Monteriggioni
Pieve a Castello

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.

View of Monteriggioni walking tour Tuscany Italy
View of Monteriggioni
About Monteriggioni

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.

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

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