
Small-Group Arezzo and Cortona Day Trip from Siena
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September 2026
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Who is going?
Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
5.0/5
Based on 6 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Small-Group Arezzo and Cortona Day Trip from Siena worth booking?
Small-Group Arezzo and Cortona Day Trip from Siena is a 8-hour experience in Siena, Italy, from $190 per person. It scores 64 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 5/5 rating across 6 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 64 / 100
- Rating
- 5/5 (6)
- Duration
- 8 hours
- From
- $190 per person
Explore the medieval charm of Lucignano and the artistic treasures of the city of Arezzo. Enjoy a farm-fresh Tuscan lunch with wine before visiting Cortona, a hilltop gem with breathtaking views and ancient history, all
What you get
- Sight-seeing time in Lucignano, Arezzo and Cortona
- Local English speaking Guide
- Roundtrip transport from Siena by minivan
- small group ensures a personalized experience
- Lunch
About this experience
Explore the medieval charm of Lucignano and the artistic treasures of the city of Arezzo. Enjoy a farm-fresh Tuscan lunch with wine before visiting Cortona, a hilltop gem with breathtaking views and ancient history, all guided by an expert in the region’s culture and heritage.
What's included
Included
- Sight-seeing time in Lucignano, Arezzo and Cortona
- Local English speaking Guide
- Roundtrip transport from Siena by minivan
- small group ensures a personalized experience
- Lunch
Not included
- Hotel pickup and drop-off
- Gratuities
What you'll see and do
Lucignano
After a short drive among the Tuscan hills, arrive at the enchanting medieval hamlet of Lucignano in the province of Arezzo and stroll through its charming streets with your local guide. The town's unique design has earned it the nickname "the town of the golden tree", the perfect location to soak in Tuscany's charming atmosphere and historic allure.
20 minutes here
Arezzo
Arrive in the vibrant city of Arezzo, a treasure trove of art, history, and architecture. Explore its stunning Piazza Grande, framed by medieval towers and Renaissance elegance. Marvel at Piero della Francesca's fresco cycle in the Basilica of San Francesco or browse the streets for shops of local crafts and products. Arezzo’s rich history and artistic heritage will captivate you at every turn. After sightseeing, retreat to the tranquility of a countryside farm for a wholesome Tuscan lunch featuring fresh, local ingredients and paired with delightful wines. Here, you’ll savor the flavors of the region together with your guide and fellow travelers
75 minutes here
Cortona
In the afternoon, visit the hilltop town of Cortona, famously depicted in Under the Tuscan Sun. Meander through its steep, picturesque streets, discover ancient Etruscan roots, and enjoy breathtaking views over the Valdichiana and Lake Trasimeno.
60 minutes here
Where it starts and ends
Meeting point
Siena
meet tour guide under the large tree that is in front of the church steps
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
meet tour guide under the large tree that is in front of the church steps
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Wed
- Group size
- Up to 8 travelers per booking
- Operated by
- Tuscan Escapes by Papilio SRL
Know before you go
- Public transportation options are available nearby
- Not recommended for travelers with poor cardiovascular health
- Suitable for all physical fitness levels
- Customers who have not reached Italy's legal drinking age of 18 will not be served alcohol
Photos



Good to know
- Duration
- 8 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Wed
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 2
- Verdict
- Solid Choice
Who runs this experience
Operated by Tuscan Escapes by Papilio SRL, who run 14 experiences we rank across 1 city, with an average Outty Ranking of 72.9 and 2 in the 90+ Club.
See everything Tuscan Escapes by Papilio SRL runsWhy this scores 64
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Small-Group Arezzo and Cortona Day Trip from Siena: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Siena.
How much does Small-Group Arezzo and Cortona Day Trip from Siena cost?
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Prices start at $190 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Siena usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Small-Group Arezzo and Cortona Day Trip from Siena take?
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Plan for about 8 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Siena is not rushed.
Is Small-Group Arezzo and Cortona Day Trip from Siena worth it?
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It holds an Outty Ranking of 64 out of 100, which we label "Solid Choice". That score blends traveler sentiment (5/5 across 6 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable most popular in Siena, and how flexible the cancellation terms are.
Can I cancel or reschedule Small-Group Arezzo and Cortona Day Trip from Siena?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Small-Group Arezzo and Cortona Day Trip from Siena suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 8-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Small-Group Arezzo and Cortona Day Trip from Siena?
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Around 2 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Siena can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Siena and add a light layer if any part of the 8-hour experience runs outdoors or after sunset.
Where does Small-Group Arezzo and Cortona Day Trip from Siena start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Siena within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Siena?
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On Outty we rank every Siena experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena, Skip the Line: Siena Duomo and City Walking Tour, Siena: A Wine Tour and Tasting Experience. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Siena?
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Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Siena?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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