THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
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.
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.
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.
Verified experiences and guided adventures in the surrounding area.
Operated by Pek Tuscany in Limo · Montepulciano, Tuscany
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.
Cortona perches at roughly 600 meters and still shows Etruscan foundations beneath its medieval facades. Walk its steep alleys and you’ll pass Renaissance frescoes and stone piazzas that remember Roman and medieval trade. Montepulciano, another hilltop powerhouse, has built its reputation on Vino Nobile—aged in colossal oak casks in cellars hewn into the limestone beneath the town. Between towns you’ll pass Lake Trasimeno, where reeds and shallow shorelines invite kingfishers and cormorants to hunt.
The day balances slow exploration with practical logistics: an English-speaking driver provides local context and drop-off in Florence after roughly eight hours of travel, visits, and tastings. Expect uneven cobbles, short uphill sections and underground cellars with cool, damp air. Bring ID for tastings, a pair of grippy shoes for steep streets, and a light layer for cellar temperatures. If you want Trasimeno added as a stop, ask in advance—the route is flexible.
This trip is best for travelers who want to pair efficient point-to-point transport with on-the-ground time in two classic Tuscan towns and authentic cellar visits—an accessible way to add rural Italy’s flavors and views to a Florence itinerary.
Pickups are offered at your Assisi or Perugia accommodation; you'll provide a specific pickup address during booking.
Two wine tastings and cellar visits are included; lunch is not included but the driver will suggest local restaurants and can escort you to options.
The vehicle and driver services are accessible, but historic town centers have steep, uneven streets and steps that may limit mobility in Cortona and Montepulciano.
Yes—stops like Lake Trasimeno can often be arranged on request, but they may change the timing of town visits so confirm during booking.
Pek Tuscany in Limo operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.
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.
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.
Cortona perches at roughly 600 meters and still shows Etruscan foundations beneath its medieval facades. Walk its steep alleys and you’ll pass Renaissance frescoes and stone piazzas that remember Roman and medieval trade. Montepulciano, another hilltop powerhouse, has built its reputation on Vino Nobile—aged in colossal oak casks in cellars hewn into the limestone beneath the town. Between towns you’ll pass Lake Trasimeno, where reeds and shallow shorelines invite kingfishers and cormorants to hunt.
The day balances slow exploration with practical logistics: an English-speaking driver provides local context and drop-off in Florence after roughly eight hours of travel, visits, and tastings. Expect uneven cobbles, short uphill sections and underground cellars with cool, damp air. Bring ID for tastings, a pair of grippy shoes for steep streets, and a light layer for cellar temperatures. If you want Trasimeno added as a stop, ask in advance—the route is flexible.
This trip is best for travelers who want to pair efficient point-to-point transport with on-the-ground time in two classic Tuscan towns and authentic cellar visits—an accessible way to add rural Italy’s flavors and views to a Florence itinerary.