A full-day private transfer linking Assisi (or Perugia) to Florence with independent visits to Cortona and Montepulciano. Includes two historic cellar tours and wine tastings—perfect for travelers who want efficient transport plus authentic hilltown time.
More ways to explore the area's outdoor wonders
Morning light slips over Umbria’s low ridges as a comfortable, air-conditioned vehicle eases out of Assisi and into the slow sweep of Tuscany’s hills. The road curves beneath cypress silhouettes; vineyards and olive groves lean toward the sun as if to share a secret. This full-day private transfer threads two of the region’s most atmospheric hill towns—Cortona and Montepulciano—before delivering you to Florence.
Difficulty
easy
Duration
8 hours (approx.)
Fitness Level
Suitable for most travelers; involves short uphill walks, uneven cobbles, and brief standing during cellar tours.
Wildlife
History
Cortona traces back to Etruscan Curtun, leaving archaeological layers under its medieval streets; Montepulciano’s reputation grew in the Renaissance as its wines were traded across Tuscany.
Conservation
Vineyard terraces and walking routes are fragile—stick to marked paths, respect private agricultural land, and support wineries that follow sustainable viticulture practices.
Reserve your spot on the PRIVATE TRANSFER: from Assisi to Florence with stops in Cortona & Montepulciano today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Wear grippy shoes
Cobbled streets and steep alleys in Cortona and Montepulciano can be slippery; sturdy shoes make walking more comfortable.
Carry ID for tastings
Italian wineries require ID for alcohol tastings; bring passports or EU ID cards for each adult.
Pack light for the vehicle
Space in a private transfer is limited—keep a small daypack to avoid crowding luggage in the back.
Reserve lunch options early
Drivers can recommend restaurants but peak seasons fill quickly—ask for a reservation suggestion or arrive slightly earlier.
Comfortable walking shoes
Good traction and support for cobbled streets and short climbs in hill towns.
Reusable water bottle
Keeps you hydrated between stops—refill from provided bottled water or taps where available.
Light jacket or layering piece
Cellars and hilltop breezes can be cool even on warm days; layers regulate comfort.
fall
Sun hat and sunscreen
Open stretches between towns are exposed—sun protection reduces fatigue in midday heat.
summer