Arezzo and Cortona Day Trip: Medieval Towns & Tuscan Lunch

Three medieval towns, one Tuscan farm lunch, and views across two valleys

A small-group day trip from Siena visits the medieval hamlets of Lucignano and Arezzo, then the hilltop town of Cortona, with a local English-speaking guide leading the route. The morning covers Lucignano's unique circular design and Arezzo's Piazza Grande and Renaissance art. After a three-course Tuscan lunch with wine at a countryside farm, the afternoon climbs to Cortona's steep streets and Etruscan sites overlooking the Valdichiana and Lake Trasimeno.

Step-by-step itinerary

Explore Lucignano, Arezzo, and Cortona

• Drive through Tuscan hills
• Stroll medieval Lucignano streets
• Explore Arezzo's Piazza Grande
• Visit Basilica of San Francesco frescoes
• Enjoy Tuscan farm lunch with wine
• Visit hilltop town of Cortona
• Walk Cortona's steep streets
• Admire views over Valdichiana and Lake Trasimeno

The experience

Eight hours means the day starts early and ends mid-evening, leaving room for the three stops without rushing through any of them. The minivan holds a small group, so the guide can answer questions and adjust the pace at each town. Lucignano comes first: a short drive into the Tuscan hills brings you to a medieval hamlet whose concentric streets earned it the nickname "the town of the golden tree." You walk those streets with the guide, who explains the town's layout and history before the group moves on to Arezzo.

Arezzo is the day's largest stop. The Piazza Grande sits framed by medieval towers and Renaissance facades. Nearby, the Basilica of San Francesco holds Piero della Francesca's fresco cycle, one of the region's most important artworks. You have time to browse the local craft shops or linger in the piazza before heading to the countryside farm for lunch. The meal is three courses built from fresh, local ingredients and paired with regional wine: eaten together with your guide and the other travelers, not rushed or served as a box. After lunch, the minivan climbs to Cortona, a hilltop town steep enough that the walk through its streets is part of the experience. The town's Etruscan roots and Renaissance churches sit alongside views across the Valdichiana valley and out to Lake Trasimeno.

The guide speaks English and knows the region's culture and heritage in detail. This is not a recorded commentary or a driver pointing out landmarks. Roundtrip transport from Siena is included, and the small-group format means you're not herded through each town on a fixed schedule.

What’s included

• Sightseeing time in Lucignano, Arezzo and Cortona.
• local English-speaking guide.
• roundtrip transport from Siena by minivan.
• three-course Tuscan lunch with local wine.
• small-group experience with personalized attention.

Before you book

Days and timesWednesdayDeparts at 09:30Last departure this season: 16 Dec

Book up toStart time

AgesAdult (3 and older) · Infant (under 3): free

GroupUp to 8

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated 2 days ago

Good to know

Low physical effortPublic transport nearbyNot recommended with heart problems

Operated by Tuscan Escapes by Papilio SRL

Is this one for you?The eight-hour day and small-group format suit travelers who want to see three distinct medieval towns without the pace of a larger tour, and who value a farm lunch and wine as part of the experience rather than a quick stop. The steep streets in Cortona and Lucignano mean comfortable walking shoes and a reasonable level of mobility matter. The itinerary is not recommended for travelers with poor cardiovascular health.

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Top questions

Can children come?

Yes. Ticket types: Infant (under 3): free.

What is Lucignano's "town of the golden tree" nickname about?

Lucignano's streets spiral outward in concentric circles from the center, a unique medieval design that resembles the rings of a tree when seen from above, hence the name. The circular layout is rare and makes the town instantly recognizable.

Can I see Piero della Francesca's frescoes in Arezzo?

Yes. The Basilica of San Francesco in Arezzo holds Piero della Francesca's fresco cycle, one of the Renaissance's most celebrated works. You have time to visit during the Arezzo portion of the day.

Is the Tuscan lunch included, and does it come with wine?

The three-course farm lunch with local wine is included in the tour price. The meal is eaten at a countryside farm and features fresh, local ingredients. You dine with your guide and fellow travelers.

What are the views like from Cortona?

Cortona sits on a hilltop overlooking the Valdichiana valley and Lake Trasimeno. The views extend across both, and the town's steep streets mean you climb to reach the best vantage points.

How much walking is involved in each town?

Each town involves strolling through medieval streets on foot. Lucignano and Cortona are both hilltop or hillside towns with steep terrain. Arezzo's Piazza Grande and surrounding streets are walkable but not flat. Comfortable shoes are essential.