Drive from Florence through the Tuscan and Umbrian hills with curated stops in Montepulciano and Cortona, two of Italy’s most characterful hill towns. This private transfer pairs cellar visits and tastings with leisurely town walks, finishing in the spiritual city of Assisi.
More ways to explore the area's outdoor wonders
Morning light lifts off Florence as your driver eases the car onto the A1, vineyards and rolling crests unfolding like page turns. You feel Tuscan hill towns approach long before the village walls appear: low stone, narrow alleys, church bells. This is a day of measured travel and local discovery.
Difficulty
easy
Duration
8 hours
Fitness Level
Suitable for most travelers comfortable with light walking and short inclines on cobbled surfaces.
Wildlife
History
Cortona dates to Etruscan origins and preserves Renaissance and Baroque influences; Assisi is a medieval pilgrimage center shaped by Saint Francis and its frescoed basilicas.
Conservation
Lake Trasimeno supports protected reedbeds and migratory birds; local wineries increasingly practice sustainable viticulture to protect soils and water.
Reserve your spot on the PRIVATE TRANSFER: from Florence to Assisi with stops in Montepulciano & Cortona today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Cobblestones underfoot
Wear sturdy, flat-soled shoes—cobbled streets and short stairways are common in both Montepulciano and Cortona.
Bring local currency
Small artisan shops and some trattorie prefer cash for quick purchases; carry small change.
Book tastings early
If you want a guided tasting led by an oenologist, request this when booking—the host can arrange cellar experts.
Protect from sun and wind
High hilltops and exposed overlooks are sunny and breezy—pack sunscreen and a light jacket.
Sturdy walking shoes
Comfortable shoes protect your feet on uneven cobbles and short stairways.
Daypack
Carry water, a jacket, camera, and any purchases while keeping hands free.
Sun hat & sunscreen
Protects against strong midday sun on hilltop overlooks.
summer
Light insulating layer
Useful for cool cellar interiors and breezy hilltops in spring and fall.
spring