Spend a long, rewarding day leaving Rome for Montepulciano’s vineyards, a three‑course wine lunch at a family winery, a photo stop at the Temple of San Biagio, and a guided tour of Assisi’s basilica. Expect cobbled streets, panoramic valley views, and a full itinerary best suited to moderately fit travelers.
More ways to explore the area's outdoor wonders
You step out of a cool air‑conditioned van onto a sunlit piazza in Montepulciano, the stone underfoot warm and the valley opening like a map of vineyards and olive terraces. The town’s slow rhythm pulls you into narrow streets lined with Renaissance facades and small enoteche pouring robust Vino Nobile.
Difficulty
moderate
Duration
12–13 hours
Fitness Level
Moderate fitness for several periods of walking, short climbs, and a long day on the road.
Wildlife
History
Montepulciano’s hilltop layout grew from Etruscan and medieval roots, while Assisi became a spiritual center after Saint Francis in the 13th century, earning UNESCO status for its frescoed basilicas.
Conservation
Support family wineries and local producers to sustain traditional agriculture; stick to marked streets and private property around vineyards and lakeshores to minimize impact.
Reserve your spot on the Tuscany & Assisi Small Group Day Trip from Rome with Wine Tasting today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Bring refillable water
Carry a 1L+ water bottle—the van has stops but walking Montepulciano and Assisi in sun depletes you quickly.
Sturdy shoes for cobbles
Choose closed shoes with good soles for uneven stone streets and short uphill sections.
Pace the tasting
A three‑course lunch with multiple pours is filling—sip between courses and hydrate to avoid fatigue.
Carry a compact power bank
Phone batteries drain fast when shooting panoramas and using maps during a long day trip.
Comfortable walking shoes
Protects feet on cobbles and short, uneven climbs in towns.
Refillable water bottle
Keeps you hydrated during long stretches between stops and while outdoors.
summer
Sun hat and sunscreen
Shields you from prolonged sun exposure on viewpoints and vineyard terraces.
spring
Portable phone charger
Ensures you can take photos and use digital vouchers throughout the long day.