About this tour
A private eight-hour drive through Tuscan countryside connects two hilltop towns steeped in medieval character. Your driver navigates you from Florence through vine-draped valleys to Cortona, where cobbled alleys and sweeping valley views have drawn artists and filmmakers for generations. Next comes Montepulciano, a ridge-top stronghold with unobstructed sightlines across two valleys. Hotel collection and return included; pace it to suit yourself.
Highlights
- Cortona's narrow stone streets and valley panoramas
- Montepulciano's ridge-top location overlooking Val d'Orcia
- Cypress-lined roads and golden Tuscan countryside
- Private Mercedes-Benz transport with air conditioning
- Optional winery visit add-on available
- Hotel pickup and drop-off from Florence
What to expect
You'll be collected from your Florence accommodation and driven south into rolling farmland. Cortona occupies your first stop—allow time to climb its stepped lanes, lean against ancient walls, and absorb the countryside from various vantage points. The drive to Montepulciano takes under an hour; once there, the town spreads itself across a hilltop with views that reward a slow walk from edge to edge. Your guide manages logistics; you decide how long to linger in each place. Bring comfortable shoes and water.
Good to know
Lunch is not included; both towns have trattoorie and cafés. The route suits all fitness levels, and all areas are wheelchair accessible. Infant seats and prams are available. Request a winery stop at booking if interested in wine tastings. Casual dress; bring sunscreen and a hat.
Tour sold and operated by Viator via Viator. Descriptions on this page are original Global Hobo summaries written by our team — not copied from the operator. Prices and availability are confirmed at checkout.