Tuscany Walking & Hiking Tour

We visit Cortona's monumental Etruscan burial tombs and learn more about the ancient practices of the Etruscan culture and its impact on the territory. Our hiking trail lies on the lower southern flank of Monte Egidio and follows gravel and dirt tracks past streams, stone houses, olive groves, and through oak forests. Evidence of Cortona's farming traditions over a span of 2000 years is gradually revealed. We stop to explore the tranquil 12th century Hermitage of Saint Francis and then continue to the town Cortona itself.

Meals: Breakfast / Lunch / Dinner

Walking time: 3-4 hours

Distance 12 km (7.5 miles) Ascent +310 m Descent 150 m

The two fortified medieval walled hill towns of Monticchiello and Montepulciano stand at over 500 and 600 meters and are connected by trails through extensive farmland of vines, olives, and oak forests. A great walk with lots of exploring and history!

Our first approach is from the famous zigzag cypress-lined road featured on the cover of brochures and television advertisements! Monticchiello feels very sleepy today with its pretty flower gardens, but during its 800-year-old history 

Monticchiello was often the object of wars and assaults, destruction, and occupations, right up until the second world war! Allow yourself to be cast back in time as you explore the narrow streets, the fortress, and ruined towers, and pop your head inside the 13th-century gothic church to see Lorenzetti's Madonna con Bambino alter piece.

Montepulciano on the other hand is a bustling little city with one winding street (1.5km) that climbs up to a charming main square, (Piazza Grande) which crowns the summit with a circle of civic buildings and a town hall reminiscent of the Palazzo Vecchio of Florence.

Meals: Breakfast / Lunch / Dinner

Walking 9.5km (6 miles), 3 hours, Ascent +150m

Siena has origins that delve deeply into the Etruscan and Roman past, but what we see here is the most beautiful and completely mediaeval cities in the world. It has imposing city walls, a Palazzo Pubblico with a tower that almost touches the sky, and a scallop shaped main square, Il Campo where the famous Palio horse race runs every year. Our local guide will deftly take you on a historic city walk through the ages and to one of the most beautiful cathedrals in the world. 

After free time to have lunch, look around and visit museums we then head to the hot thermal baths of Rapolano Terme to relax and swim in these healing waters and enjoy unique views of Tuscany at sunset. Change ready to enjoy an evening stroll (the Italian Passeggiata) and dinner in a local restaurant.

Meals: Breakfast / Dinner

Walk: City walking tour 2 hrs

We set out on foot from our farmhouse and head into the hills to walk gently up the hill to Cortona passing through tiny hamlets of stone houses, walking along ancient Roman basalt tracks, and through olive groves.

We enter Cortona via one of the ancient city gates and wind along narrow streets of fascinating historic monuments. After lunch, we visit the Etruscan museum with a guide, and then there is free time to indulge in a gelato or sit with a cappuccino in a café. 

Meals: Breakfast / Lunch / Dinner

Walking time: 3 hours, Distance 9.5 km (6miles), Ascent +300 hm

We journey to Pienza, famous for Pecorino cheese and Renaissance architecture. The town of Pienza was built in 1458 on top of the old village of Corsignano at the request of Pope Pio II Piccolomini as a symbol of the Italian Renaissance. From the walls of the city, you get some of the most beautiful views in Tuscany -the breathtaking Orcia valley, immortalised in 2000 in the Gladiator film. From here we step out into its rolling hills with the walls and towers of the mediaeval village of San Quirico D'Orcia beckoning us. 

We are now on the Via Francigena, which has seen the passage of pilgrims and popes, knights and mercenaries, kings and emperors. All have walked the same country lanes and woodland tracks to reach the mineral-rich waters at Bagno Vignoni and bathe in its hot pools of bubbling volcanic water. Fancy dipping your feet in? No problem!

Meals: Breakfast / Lunch / Dinner

Walking time: 3-4 hours, Distance 12 km (7.5 miles), Ascent +150 m Descent 250 m

A spectacular drive through the Crete Senesi takes us to the abbey. The beautiful frescoes in the cloisters, painted by Renaissance artists, Sodoma and Signorelli tell the story of the life of Saint Benedict.

Our scenic walk gives us plenty of time to admire the contrasts in this unusual and desolate landscape of ochre-colored hills. We arrive at the walled village of Buonconvento to enjoy a gelato and think about the pilgrims on the Via Francigena who stopped to rest here on their way to Rome.

Meals: Breakfast / Lunch / Dinner

Walking time: 4-5 hours, Distance 16 km (10 miles), Ascent +100 m Descent 340 m

Drop off at Terontola-Cortona station with direct trains for Rome and Florence (10 mins away).

Meals: Breakfast