Discover Tuscany

Self-guided walking holiday in Italy

From £ 550.- / 8 days

Price per person based on 2 people sharing

  • One accommodation
  • Self-guided walking holiday
  • view on the apennine mountains that the base for this Italy walking holiday in Tuscany
  • Autumn in Tuscany
  • View on a medieval town in Tuscany

Tuscany is a timeless region of great natural beauty and wide-open spaces, and a very popular destination for walking holidays in Italy.

This self-guided walking holiday will lead you along archetypal Tuscan landscapes, cypresses, olive groves, honey-coloured stone farmhouses and fields of sunflowers. It is also packed with cultural and historic interest, hidden art treasures and more antiquarian sites than anywhere else on earth.

Your base for this holiday, a tiny village in the Apennine mountains, is ideally located for walking; it is surrounded by leafy valleys, ravines and several national parks, the whole area is dissected by networks of trails and old mule tracks.

Accommodation in Tuscany

You will stay in a villa in the small village Caprese Michelagelo. The villa is set in 10 acres of beautiful mountain forests and is surrounded by olive groves. The tranquil location was used in centuries passed as a retreat for the Francescan Monks from the nearby monestry. Accommodation is in suites which have been lovingly and elegantly restored with terracotta floors, chesnut beams and local stone. Apartments are self-contained with twin or double beds, kitchen facilities and bath / shower rooms. The apartments open onto a beautiful Tuscan courtyard with a large gazebo, gently shaded by vines. All bed linen, towels and toiletries are provided. In the surrounding garden there is a swimming pool, heated by solar panels, and there is also a small fitness room for guests to use.

Exterior of hotel accommodation for this Tuscany walking holiday in Italy bedroom of hotel accommodation Swimming pool and gardens of hotel accommodation

Breakfast is served buffet-style al fresco in the courtyard. It is also possible to upgrade this Tuscany walking holiday to an all inclusive package where picnic lunches and 7 dinners are included. Please contact the holiday provider, through the holiday enquiry form for more information.

Walking in Tuscany

Young couple enjoying a woodland walk during the Tuscany walking holiday in Italy View on the sea and Tuscany coast

This Italy walking holiday offers many circular routes for walkers of all abilities start right from the doorstep of your accommodation, but many other itineraries are also available. For example the 25-mile Sentiero Francescano della Pace from Assisi to Gubbio that retraces the route St Francis is said to have taken in the very early 13th century, a journey he made just after he had renounced his earthly riches. The walks are by their very nature leisurely, allowing time to explore the cultural treasures you pass along the routes or enjoy the views. You will be provided with walk descriptions based on your interests and wishes. Many optional guided excursions to nearby towns and cultural sights are also available, at additional cost.

To reach the start point of some of the walks, transport is required and car hire is recommended. However, a fully inclusive package is also available at additional cost that includes among others transport to the starting point of all walks, and two guided excursions.

Tuscany walking holiday example walks

Traditional Tuscany buildings and bridge Woodland path in a Tuscany woodland

There is a wide variety of self-guided walks available to choose from, these are just a few examples;

Walk 1 - Castles & Rivers. About 16km/10mi - From the centre of Anghari, visit two historic & strategically important castles and walk along the river Sovara. Castello di Galbino, near the village of Tavernelle, dates back to the year 1000, and today is transformed into a villa with a turret in the centre of the roof and a small round towers at each corner. Walking along the left bank of the river Sovara, you will arrive at the hamlet of Molino Bianco then continue onto Pieve di Sovara, dating back to the late medieval period it lies near the intersection of two Roman roads one connecting Monterchi and Citta di Castello (The Crinale) and the other from Arezzo. A little further on you will arrive at Castello di Sorci. Now a farm, housing a typical Italian restaurant, in it's heyday it was the seat of power for three influential families: The Tarlati family from Pietramala (1234-1388), The Baldaccio family (1388-1441) and the Pichi family (1443-1650). It was destroyed and rebuilt several times. It is said that the ghost of Baldaccio of Anghari, betrayed and subsequently beheaded on the 6th September 1441, is still active appearing every 50 years on the anniversary of his death.

Walk 2 - Bridges & Forests. About 16km/10mi - From Ponte Alla Piera and it's historic Roman bridge through woods of Chestnut & Beech. Starting at ancient Roman bridge, this walk follows a footpath which goes up from the middle of the town directly into chestnut woods. After several ups and downs and twists and turns, the path ascends until it reaches Poggio Traversa (942m) where beech trees become more predominant. Continuing on the footpath you get to Monte Filetto (1289m) where you will take a lovely forest to Monte Castello (1414m), an important peak in the mountain range of the Alpe di Catenaia, from where you will be able to take in stunning vistas. On the descent, the terrain opens up offering wonderful views as you pass through Poggio il Soglio (981m), Poggio il Capanno (765m), until Cerreto.

Walk 3 - The Roman Road. Leaving Passo della Scheggia (588 metres) you follow the path of the Via Ariminensis built in 208 BC by Livio Salinatore and joined Aretium (Arezzo) to Ariminum (Rimini) on the Adriatic sea. In Roman times it constituted the back bone for military and commercial traffic. At the foot of Castello di Montauto, near to a hunter's hut, you can chose to carry on through the woods, which offers wonderful views of the mountain range of Monti Rognosi and the High Tiber Valley, or follow a path which crosses the northern slopes of Monte della Croce, with views of the Alpe di Catenaia, Ponte alla Piera and the narrow valley of the Sovara. Either route will bring you to "il Conventino" (464m), from where, descending down to and crossing the stream of the Sovara, you take the Strada Provinciale (Provincial road) in the direction of Caprese Michelangelo to Ponte alla Piera (560m).

Walk 4 - In the Pinewoods. A beautifully simple, circular walk right around the hill-side of Monti Rognosi/Lago Montedoglio that offers outstanding views across the High Tiber Valley. Leaving Poggio Castiglione you go through the pinewoods for a short distance, passing the remains of an old copper mine and a view of the remains of Castello di Castiglion Fatalbecco. As you continue on down the hillside you come to the rest area at the crossroads, from where the route becomes immersed in the pinewoods with views of the Lago Montedoglio and the upper reaches of the River Tiber. The forest path leads towards the Carmine allowing you to explore the western side of the mountain, with views of the narrow valley of the Sovara stream and the rest of the Monti Rognosi hills. The path ends in the area known as "Omo Morto" (Dead Man) and from here, going through Col di Paiolo, you return to the start point.

Dates and availability

Autumn light in a golden coloured autumn woodland Group taking a break during the Tuscany walking holiday in Italy

The Discover Tuscany self-guided walking holiday in Italy is completely flexible and can start on any date, subject to accommodation availability. Upgrades to a fully inclusive package that includes airport transfers, transfers to the start of walks, two guided excursions, all lunches and evening meals are also available. Please contact the holiday provider, through the contact form, for more information.

Location self-guided walking holiday - Discover Tuscany - Italy

Holiday type

One accommodation Self-guided walking holiday
Self-guided walking holiday
Board basis: Bed & Breakfast


From £ 550.- / 8 days

Price per person based on 2 people sharing


7 nights Accommodation, Breakfast, walk and route descriptions

Not included

All other costs, including travel costs to the starting-point of this holiday and car hire

Walking holiday reference


Walking grade

Walking holiday in hills only
  • Hills
  • Easy walking
Walking holiday in low to high mountains
  • Low to high mountains
  • Moderate walking

Best time of the year

March - November

Walking Holiday by:

Villa Michelangelo


Contact details

Languages spoken

English, Italian

Getting there

  • Perugia (58 mi)
    Bologna (71 mi)
    Rimini (80 mi)
  • Location map

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