Assisi above the Umbrian valley
Home / Journeys / Vineyards, Food and Frescoes – Italian Road Trip in Tuscany and Umbria
8 nights · Florence · Car

Vineyards, Food and Frescoes - Italian Road Trip in Tuscany and Umbria

Ghiberti’s bronze doors, an unfinished Michelangelo, and vineyards the whole way from Chianti to Montepulciano – eight nights through Tuscany and Umbria at the pace of a good lunch.

From£2,400pp
Duration9 days
StyleSelf-guided
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An independent Stradora pick. Details from the operator's published information, last checked 1 Nov 2026. Stradora DiscoveryChosen independently by our editors because we think it's worth the drive. We're not partnered with this operator: dates, prices and booking are handled by them, and we last checked their published details on 1 Nov 2026.
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The route

Nine days from Florence into Umbria at the pace of a long lunch, which is the correct speed for this part of Italy. Two nights in each of four places and very little driving between them.

Florence opens it with skip-the-line access to the Duomo museum complex, which is the better half of the cathedral: Brunelleschi’s dome, the Baptistery, the Campanile, the crypt, Ghiberti’s gilded bronze Gates of Paradise, and an unfinished Michelangelo where the figures are still half inside the marble. A private tour of the Accademia and the David can be added.

Chianti follows for two nights of vineyard visits and Romanesque churches, with an optional trip to Siena for the Palio, the bareback horse race run around the Piazza del Campo twice each summer. Cortona comes next, staying at a historic villa with vineyards and old tobacco-drying fields in the grounds, and Arezzo is nearby for Piero della Francesca’s fresco cycle in the Basilica of San Francesco, which is among the finest in Italy and far less visited than it deserves. Montepulciano and its wine are an optional addition.

Perugia closes the trip, a city with Etruscan walls, Roman gates and medieval streets stacked on top of each other, with Assisi an optional day out. Original Travel include the hire car, the accommodation, a private transfer on arrival, the Duomo tickets, local concierge access, a 24-hour helpline and carbon absorption through their own programme. Flights and most meals are separate, the car is collected in Florence and returned at Perugia airport, and prices run from 2,400 to 3,600 pounds per person.

Style
Self-guided
Duration
A week or so (8-11 days)
Region
Europe
Vehicle provision
Vehicle provided
Departures
Flexible, tailor-made
Starts/ends
Florence, Italy to Perugia, Italy
Run by
Independent specialist operator

What's included

  • Hire car
  • accommodation
  • private transfer on arrival
  • skip-the-line Duomo Museum tickets
  • local Concierge access
  • 24-hour helpline
  • carbon absorption on the trip's footprint (operator's own programme).

Not included

  • Flights
  • meals beyond those specified
  • not itemised in full.

Ready to drive it?

9 days, from £2,400pp

Independent Stradora pick
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