If you’re looking for a week of hiking in Italy that feels both active and genuinely relaxing, you’re in the right place. Based at Agriturismo Dogana near Lake Trasimeno, this 7-day experience takes you through the rolling Tuscan hills, the iconic landscapes of Val d’Orcia, Via Francigena, the Way of St. Francis and and the dramatic scenery of the Sibillini Mountains with an official hiking guide, carefully planned logistics, and delicious meals waiting for you at the end of each day.
This is not a bootcamp. We hike at a vacation pace, with breaks for viewpoints, photos, and simple enjoyment. You can join either a Women-Only Week or an Open Group Week (all genders welcome). Group size is limited to keep the atmosphere friendly and the experience smooth.
Program of the week
Day 1: Arrival at Dogana & meet Giacomo
Pickup from our nearest train station and afternoon check-in at the estate.
Meet your hiking guide, Giacomo, for a short welcome briefing covering pace, equipment, and the week ahead.
7.00 pm farm-to-table dinner at La Dogana.
Day 2: Montegualandro Castle
Breakfast at the venue.
9:30 am departure directly from La Dogana for a scenic 14 km hike with gentle elevation and wide lake views.
Packed lunch on the trail, followed by return transfer to the venue.
Dinner at La Dogana.
Day 3: Cortona and Tuscan hills
Breakfast at the venue.
9:30 am transfer to Le Celle di San Francesco, just outside Cortona.
A 14 km moderate hike through olive groves, woodland, and rolling Tuscan landscapes, with a packed lunch en route.
Free time in Cortona before returning to La Dogana for dinner.
Day 4: San Casciano dei Bagni
Breakfast followed by a relaxed morning at the estate.
Lunch at La Dogana, then early afternoon departure for San Casciano dei Bagni.
A 15 km hike through the surrounding countryside, ending near the thermal waters at around 6:00 pm.
Return transfer and dinner at the venue.
Day 5: Val d’Orcia, San Quirico & Pienza
Breakfast at the venue.
9:30 am departure by transfer toward Pienza and the Val d’Orcia.
A 14 km moderate hike connected to the landscapes of San Quirico d’Orcia, with packed lunch during the walk.
Free time in Pienza before returning to La Dogana for dinner.
Day 6: Monti Sibillini & Lake Fiastra
Breakfast at the venue.
9:30 am transfer toward the Monti Sibillini for a full day in one of central Italy’s most dramatic mountain landscapes.
Guided hike with packed lunch, followed by time at Lake Fiastra in the afternoon.
Return to La Dogana for a final dinner together.
Day 7: Goodbye
Breakfast, farewells, and return transfer.
All hiking routes and timings may be adjusted slightly according to weather conditions and group pace.
Getting here, easy for international guests
Our nearest train station is Terontola–Cortona. We include a scheduled pick-up on arrival day and a scheduled drop-off on departure day.
If you prefer, we can also arrange airport pick-up (Perugia / Florence / Rome) for an extra fee.
What is included
Your week includes 6 nights accommodation in apartments at Agriturismo Dogana, 6 breakfasts, 6 dinners (wine included), 5 packed lunches / picnics plus 1 lunch at the venue. You will hike with an official hiking guide every day, and all transfers for the hikes are included, as well as the scheduled train-station pick-up and drop-off at Terontola–Cortona. VAT is included.
Who this experience is perfect for
This week is ideal for guests who want a guided hiking holiday with comfort and good food without the pressure of intense athletic goals. Most hikes are easy to moderate, and we always prioritize safety, pacing, and enjoyment. You should be comfortable walking 4-5 hours with breaks.
Book your hike holiday
Tell us your preferred date, time and number of guests, and we’ll get back to you with availability and confirmation. The experience is subject to availability and may be adapted to the season.
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