5 hrs walking / Difficulty: moderate – strenuous

Wind through the streets of Montepulciano, known as the pearl of Renaissance, admiring its wonderful buildings. We then visit the Cantina del Redi, where Vino Nobile is aged in vaulted caves beneath the foundations of the city. Leave the town through the ancient gates, passing the church of San Biagio and walk through pictoresque countryside to Montichiello. Time to explore this tiny hamlet before continuing to Pienza, a marvel of the 15th century, completely rebuilt by Pope Pius II to create the setting for the "ideal" society which we can still admire today.

5 hrs walking / Difficulty: moderate

Begin the walk at the fortified village of Montefollonico standing on a ridge between the Val D’Orcia and the Val di Chiana. After enjoying its sleepy atmosphere, leave thought the thick oak woods and descend gradually, emerging into an open landscape of cultivated fields, pretty vineyards and rolling hills. The view approaching Montepulciano is spectacular. On the way to the old town you will pass the Tempio di San Biagio, one of the great churches of the high Renaissance and enter Montepulciano though one of its ancient gates.

5 hrs walking / Difficulty: moderate – strenuous

The walled hill-town of Montalcino, famous for its Brunello wine, is the starting point of this beautiful day. After a visit of the town, make your way to the battlements of the Rocca castle for a spectacular view of the Val D’Orcia. A few miles down the valley is the beautiful 8th century Romanesque abbey of Sant Antimo and the start of the walk where you will ascend a trail lined with cypresses and oaks. Continue to Castello di Ripa D’Orcia and end with a swim at the restorative hot springs in the charming hamlet of Bagno Vignoni.

3 hrs walking / Difficulty: easy – moderate

A spectacular drive through the Crete Senese landscape takes you to the Benedictine abbey of Monte Oliveto. Take your time to admire the amazing 16th century frescoes by Sodoma & Signorelli telling the story of St Benedict. The walk offers gorgeous views of a very different countryside as you walk up to the little village of Chiusure with a wonderful opportunity to look back at Monte Oliveto standing in the midst of tall cypresses. It continues on along a ridge until you reach San Giovanni d’Asso.

CIRCULAR WALK

3 hrs walking / Difficulty: easy – moderate

This wonderful walk takes you through some of the most delicately attractive countryside in Chianti and to one of the most impressive castles in Tuscany, summer residence of the Ricasoli family since 1067, when they purchased it from the Vallombrosan monks. Bettino Ricasoli, who died in 1880, was responsible for the blend of grapes that gave us Chianti Classico and he was also the second Prime Minister of the new united Italy. The magnificent views from here stretch to Monte Amiata, Siena and beyond. This is a gloriously area for taking photos, while you walk through some of the most serious wine country in Italy.

4 hrs walking / Difficulty: easy – moderate

Starting in Panicale, a charming small town south of Lake Trasimeno with an unexpected setting and snail shaped medieval streets, walk along a ridge with pretty views of the lake and into to the walled hamlet of Paciano through one of its three gates. Climb to Monte Petrarvella and the Cappuccini monastery set in oak, pine and chestnut woods, descending back into Panicale.

5 hrs walking / Difficulty: moderate – strenuous

A wonderful walk with stunning views of the Umbrian Apennines awaits us, high in the hills behind Gubbio. This walk will lead you through high pastures, woods, and old farmhouses. Leave the Regional Park and visit Sant'Ubaldo to see the giant candlesticks kept in this monastery perched on the hillside of Monte Ingino. Take the cable car to enjoy wonderful views of the roof tops and monuments and make a dramatic entrance into Gubbio, perhaps the most beautiful of Umbrian towns.

5 hrs walking / Difficulty: moderate – strenuous

Travel to Assisi, visiting the churches of Santa Maria degli Angeli and San Damiano on the way to the hermitage of St Francis, Eremo delle Carcere, set above Assisi in secluded woodlands, a very spiritual place. The walk ascends to the top of Monte Subasio where wild horses roam. From here, on a clear day, there are 360 degree views over the whole of Umbria. The walk then winds down through olive groves and into the medieval streets of Spello, an enchanting town of Roman origin.

4 hrs walking / Difficulty: moderate

Leave early to reach Spoleto in time to enjoy your wander through this graceful Italian hill town. Its origins go back as far as the Bronze Age. It was important as a Roman colony and later in the Middle Ages as an independent Duchy, finally annexed to the Papal States. The walk starts at the Ponte delle Torri aqueduct, an astonishing piece of medieval engineering, which spans 240 mt across the Tessino gorge. The scenic walk goes to Castelmonte and through beautiful woods to the top of Monteluco and then descends again into Spoleto where, time permitting, you can spend a little more of the day.

2 hrs walking / Difficulty: easy

Travel to Orvieto, which sits majestically on top of a tufa plateau. Visit the Cathedral whose facade is one of the most beautiful in all Italy. Afterwards take a tour of the underground Ipogeo of the city. Time to explore the wonderful historic town. In the afternoon continue to Civita di Bagnoregio. Walk across a causeway bridge to reach the village perched unbelievably on an eroding clay promontory. Descending a tiny footpath at the far end of Civita, pass through an Etruscan tunnel and a chestnut wood to approach the ‘calanchi’ clay erosions with wonderful photographic opportunities of Etruscan tomb openings in the cliffs and dramatic crumbling crags.