Tuscany: hilltop towns of Val d’Orcia & Siena
Travel through the most iconic cultural landscape in Italy and experience a beautiful explosion of natural and cultural heritage throughout this amazing self-guided walking tour. The Tuscan landscape of the Val d’Orcia will charm you with its vineyards, scenic farmhouses, green forests, and peculiar iconic eroded clay slopes. As you advance through the wonders of the Tuscan countryside, you will discover captivating settlements such as the hot spring hamlet of Bagno Vignoni and the Renaissance city of Pienza. A true cocktail of experiences, this independent hiking itinerary brings you to beautiful palaces, thermal baths, Romanesque churches, and tempting local wineries while walking through beautiful valleys, playful rivers and enchanting forests. Enjoy an exciting trip deep into the pearl of central Italy hopping from one hilltop village to the next.
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Destination
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Duration8 Days I Level: 2 (of 5)
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What is includedAccommodation in 3* hotels and agriturismo incl. breakfast (check the Rates&Remarks tab for details); Luggage transportation (1 piece per person, up to 20kg!); People transfer (on Day 4 (to Castelnuovo), on Day 6 (Buonconvento-Monte Oliveto Maggiore Abbey) and on Day 7 (Buonconvento-Monteroni d'Arbia); Detailed roadbook and map in English (incl. access to GPS tracks); Emergency hotline
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What is not includedDrinks and other meals; Other transfers/Public transportation; Possible CITY TAX to be paid in cash on the spot (it varies depending on the city and on the hotel’s category; appr. 1-4 Euro per person per night)
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Best periodApril, May, June, July, August, September, October
Day 1. Arrival at Montepulciano
Day 2. Montepulciano - Pienza (13-15km, 4hrs, +390m/-500m)
Day 3. Pienza - Bagno Vignoni (12km, 4hrs, +200m/-420m)
Day 4. Bagno Vignoni - Castelnuovo - Sant’Antimo - Montalcino (13km, 4,30hrs, +450m/-280m)
Day 5. Montalcino - Buonconvento (15-18km, 5hrs, +320m/-620m)
Day 6. Loop walk to Monte Oliveto Maggiore Monastery (14km, 4,30hrs, +390m/-480m)
Day 7. Monteroni d’Arbia - Arbia; train to Siena (10km, 3,30hrs, +230m/-190m)
Day 8. Departure day
TOUR LOCATION
Price (2026)
Single room & Solo Traveler supplement
Tips
Accommodation
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