About this tour
A scenic eight-hour drive from Assisi to Florence that breaks the journey across Tuscany's most compelling stops. You'll spend time in Cortona, the hilltop town famous from Under the Tuscan Sun, then move on to Montepulciano for cellar visits and tastings of Vino Nobile and other regional reds. Your private driver handles navigation whilst you soak in the Val d'Orcia landscape—vineyards, cypress groves, and medieval stone villages stacked on ridges. Lunch is yours to arrange with local recommendations.
Highlights
- Cortona's 600-metre perch overlooking Lake Trasimeno valley
- Two working cellars with massive oak barrel collections
- Four wine tastings: Vino Nobile, Super Tuscan, Brunello, regional red
- Private air-conditioned vehicle with experienced local driver
- Medieval town exploration at your own pace
- Flexible lunch stop with driver's restaurant tips
What to expect
You'll be collected from your Assisi base and driven northeast into the clay hills. Cortona commands attention from below—narrow lanes, Renaissance frescoes, sweeping vistas over farmland. Plan two to three hours there. Montepulciano follows, a steeper, longer main street lined with Renaissance palaces. The cellar visits are the centrepiece: you'll descend into cool stone chambers where massive wooden barrels age the region's signature Vino Nobile. Tastings include food pairings. The drive to Florence takes roughly two hours, arriving mid-afternoon at your hotel or station.
Good to know
Bring comfortable walking shoes for both towns—cobbled streets and slopes dominate. Lunch isn't included, so budget accordingly; the driver will point you to good trattorias. Wine tastings are generous; eat beforehand if you're alcohol-sensitive. Montepulciano sits at 600 metres; summer heat can be intense.
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.