Private Full-Day Tour of Assisi and Cortona from Florence
Two timeless hilltop towns, one extraordinary day through Umbria and Tuscany.
This private full-day tour of Assisi and Cortona from Florence takes you on a curated journey through two of central Italy's most storied destinations, traveling in comfort with your own dedicated chauffeur from door to door.
Assisi greets you with its luminous streets of pale stone, its medieval churches and the enduring legacy of St. Francis and St. Clare. A short afternoon drive then brings you to Cortona, the hilltop Tuscan town made famous by the film Under the Tuscan Sun, where Etruscan walls meet Renaissance art and sweeping views stretch across Lake Trasimeno.
Because this is a private tour, the pace is entirely yours. Linger at a fresco, stop for a glass of local wine, or simply soak in the landscape — your chauffeur is on hand whenever you are ready to move on.
The countryside between Umbria and Tuscany unfolds outside your window during every transfer, offering rolling hills and cypress-lined roads that are a reward in themselves. Few day trips from Florence manage to combine this much history, scenery and atmosphere in a single itinerary.
Tour Highlights
Visit the Basilica of St. Francis in Assisi, home to Giotto's celebrated fresco cycle and one of Italy's great masterpieces of medieval architecture.
Explore a church built directly over an ancient Roman temple, one of Assisi's most curious and atmospheric sites.
Enjoy panoramic views over Lake Trasimeno from the ramparts of Cortona, a view that changes with every season.
Travel through the scenic countryside between Umbria and Tuscany aboard a private vehicle with a dedicated chauffeur.
Walk the quaint alleyways and pink-and-white marble facades of Assisi at your own relaxed pace.
Discover Cortona's rich layering of Etruscan relics, medieval buildings and Renaissance works in a single compact town.
Return to Florence whenever you are ready — the itinerary is fully flexible and completely private.
Itinerary
Your private chauffeur meets you at your Florence accommodation and you set off through the Tuscan and Umbrian countryside toward your first destination.
You are dropped off in Assisi, where pale stone streets radiate a calm intensity rooted in the memory of St. Francis and St. Clare. The town's architecture, from Romanesque churches to medieval alleyways, rewards unhurried exploration.
Admire the Basilica of St. Francis, with its remarkable white-and-pink marble facade and the celebrated fresco cycle attributed to Giotto. You will also have the chance to visit the unusual church constructed over a Roman temple, one of the town's most distinctive landmarks.
Take time for lunch at one of Assisi's local restaurants before your afternoon transfer. Umbrian cuisine — featuring truffles, legumes and cured meats — is well worth the pause.
Your chauffeur drives you to Cortona, a hilltop town layered with Etruscan, medieval and Renaissance heritage. Walk its steep lanes, visit its churches and museums, and pause to enjoy views that reach across Lake Trasimeno toward the Apennines.
When you are ready to head back, simply let your chauffeur know and they will take you directly to your Florence accommodation to close out the day.
What Is Included
Included
- Private chauffeur for the full day
- Hotel pickup and drop-off in Florence
- Air-conditioned private vehicle
- Flexible return time
- All transfers between Assisi and Cortona
Not Included
- Entrance fees to churches or museums
- Lunch and beverages
- Gratuities (discretionary)
- Personal travel insurance
Important Information
Reserve Your Private Day Out
Secure your private chauffeur and spend a full day exploring two of central Italy's most beautiful towns at exactly your own pace.
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