About this tour
A 10-hour day trip from Rome that sweeps you through Tuscany's rolling hills to two hilltop towns—Cortona and Montepulciano—where Renaissance architecture meets countryside vistas. You'll drive past vineyard-stitched valleys, taste local wines, and sample regional food on your own dime. Private car, air conditioning, and onboard WiFi make the 2.5-hour journey north comfortable enough that you arrive ready to explore rather than knackered.
Highlights
- Medieval hilltop villages Cortona and Montepulciano
- Vineyard-studded Tuscan landscape from the car
- Wine tasting at a local producer
- Regional food and produce sampling
- Private transport with AC and bottled water
- Parking and tolls included
- WiFi onboard for the drive
What to expect
You'll be collected in Rome and driven north into wine country, arriving at Cortona mid-morning. The town climbs steeply; narrow medieval streets lead past stone facades and Renaissance art. Spend a few hours wandering, then move to Montepulciano, another fortified village with similar character but different angles. In between—or at either stop—you'll taste wines from a local cantina and try cheeses, cured meats, and oils typical of the region. Bring euros for lunch; your driver will know spots. The return to Rome takes the late afternoon, arriving around 8 p.m.
Good to know
Both villages have steep cobbled streets and limited wheelchair access in their medieval cores, though vehicles and some ground-floor attractions are accessible. Pack comfortable walking shoes, hat, and sunscreen. Lunch isn't included; budget €15–25 per person at family trattorias. The drive itself is scenic but long—bring a book or enjoy the countryside.
Tour sold and operated by Viator via Viator. Descriptions on this page are original BugBitten summaries written by our team — not copied from the operator. Prices and availability are confirmed at checkout.