Walking Holidays in Tuscany and Umbria

The landscapes vary depending on your chosen itinerary.

On the Via Francigena and in the Chianti region, you can expect the classic Tuscan scenery of rolling hills, cypress-lined paths, and gravel roads.

Other areas, such as northern Tuscany, feel more rugged and medieval, while Umbria, one of Italy’s greenest regions, offers deep forests and serene countryside trails.

If you need assistance, our team is here to help you select the perfect itinerary.

If you’ve found a Tuscany walking holiday or an Umbria hiking tour that matches your travel dreams, you have two options:

1. Send us an email at info@sloways.eu or call us at (+39) 0552340736. We’ll ask for some basic trip details, such as the number of travellers, preferred departure date, and any special requests.
2. Use our online calculator on each trip page to receive a provisional price for your chosen tour. If you’re happy with the estimate, send us a request and we’ll confirm hotel availability before finalising your booking.

In larger cities and tourist areas, you’ll often find English speakers.

However, in rural areas and small villages, it is less common.

Knowing a few basic Italian phrases can help – and when in doubt, gestures and translation apps usually do the trick.

We provide charming accommodations in B&B, farmhouses, and 3-star hotels, all with private rooms and bathrooms.

These stays combine comfort and authenticity, allowing you to fully immerse yourself in the Italian walking experience.

All our Tuscany and Umbria walking holidays are self-guided, meaning there is no fixed group or guide.

Travellers enjoy their own adventures using detailed documentation prepared by our local experts.

We take care of the logistics, including booking accommodations and transporting your luggage, so you can walk freely and focus on the journey.

Both regions reward walkers who time their trip well. The terrain ranges from low rolling hills and gravel roads to forested Apennine ridges, so season matters more than it does on flatter routes.

• Spring (April to June) is the most popular window. Temperatures are mild, the countryside is green and in bloom, and the light across the Val d'Orcia and the Umbrian valleys is at its most beautiful.

• Autumn (September to October) is an equally strong option. Cooler than summer, with the colours of the harvest season among vineyards and olive groves, and noticeably fewer walkers on the trails.

• Summer (July to August) is possible but demanding, especially on exposed sections of the Via Francigena and the higher stretches of the St Francis Way.

• Winter (November to March) is not recommended for most itineraries. Higher sections can be cold and wet, and some smaller accommodations operate on a seasonal basis only.

Best window: late April to early June, or mid-September to mid-October. These months combine the most comfortable walking conditions with the most rewarding landscapes in both regions.

Every SloWays walking holiday in Tuscany and Umbria is fully organised so you can focus entirely on the walk.

Here is what is included as standard:

• Pre-booked accommodation in B&B, farmhouses, agriturismi, and 3-star hotels, all with private rooms and bathrooms

• Luggage transfer from one stage to the next, so you walk with a light daypack only

• Detailed route notes, maps, and a digital information pack prepared by our local experts

• GPS navigation via app, available offline on iOS and Android

• 7-days-a-week assistance and emergency support throughout your trip

• Basic medical and luggage insurance on most itineraries

The exact inclusions vary by itinerary. Check each trip page for the full details.

Both routes pass through this part of Italy, but they are very different walks in terms of origin, character, and landscape.

Via Francigena

• A medieval pilgrimage road connecting Canterbury to Rome, used for over a thousand years by pilgrims, merchants, and crusaders

• In Tuscany, it runs from the Apennine passes near Pontremoli south through Lucca, Siena, and the Val d'Orcia toward Rome

• The landscape is quintessentially Tuscan: cypress-lined hills, gravel roads (strade bianche), medieval walled towns, and rolling vineyard country

• The route is well-marked and well-served with accommodation throughout Tuscany

• Character: historic, grand in scale, and deeply connected to European pilgrimage culture

St Francis Way

• A route tracing the life and travels of Saint Francis of Assisi, running from Florence (or Rimini) through Chiusi della Verna, Assisi, Spoleto, Rieti, and on to Rome

• It crosses both Tuscany and Umbria, with some of its most significant sections around Assisi, Spello, the Hermitage of the Carceri, and the forests near Spoleto

• The landscape is wilder and more forested than the Via Francigena, with Apennine ridges, hermitages, and remote valleys

• Character: intimate, meditative, and rooted in Franciscan spirituality and nature

Which should you choose?

• Choose the Via Francigena if you are drawn to iconic Tuscan scenery, medieval history, and one of Europe's great pilgrimage roads.

• Choose the St Francis Way if you are looking for a more spiritual or contemplative experience, wilder terrain, and the green heart of Umbria.

• If you cannot decide, SloWays also offers a combined Via Francigena and St Francis Way experience that links both routes into a single journey.