Small-Group Arezzo and Cortona Day Trip from Siena
Siena, Italy

Small-Group Arezzo and Cortona Day Trip from Siena

Outty Ranking 65 5.0 · 6 traveler reviews8 hoursFrom $217
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Outty Ranking

65/100

Solid Choice. Our proprietary evaluation. How we score

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 $217 per person. It scores 65 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
65 / 100
Rating
5/5 (6)
Duration
8 hours
From
$217 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 guided by an expert in the region’s culture and heritage.

What you get

    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

    1. 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

    2. 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

    3. 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

    Small-Group Arezzo and Cortona Day Trip from Siena, photo 2Small-Group Arezzo and Cortona Day Trip from Siena, photo 3Small-Group Arezzo and Cortona Day Trip from Siena, photo 4

    What travelers are saying

    Outty’s summary of the themes that recur across 6 traveler reviews. Written by us, not quoted from reviewers.

    Food and drink

    6 mentions

    The tastings and food stops are a highlight for most reviewers.

    The guide

    5 mentions

    Travelers single out the guide as the reason the experience works.

    Knowledge and storytelling

    3 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Photo opportunities

    3 mentions

    The views and photo stops come up again and again.

    Small groups

    2 mentions

    The group size is repeatedly described as intimate rather than packed.

    Traveler reviews

    6 verified traveler reviews for Small-Group Arezzo and Cortona Day Trip from Siena. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    6
    4 star
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    3 star
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    2 star
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    Sort
    589clydes · May 2026

    GaTech67

    The trip was amzzing with beautiful scenery. Our guide was very informative and added many sidenotes about the area, history and culture to add to the experience. Cortona and Arezo were amazing towns with a rich history and I really took a lot of pictures. The guide gave us plenty of insights into the cities and thinghs to see before we ventured into each city. The wine tasting experience was amazing with great food and wine.

    via Tripadvisor

    Jet801755 · July 2024

    Tuscan Wine Tour

    Our wine tour was on June 19, 2024. Our tour through Tuscan Escapes was excellent. Our guide Marco was wonderful and extremely knowledgeable with regard to the geography we were traveling through and the wine growing process. He paced the tour in a way we never felt rushed and were able to enjoy the two wineries we visited. Marco had a great rapport with the owners of each. If we were to return to Tuscany we would use Tuscan Escapes and definitely request Marco as our guide.

    via Tripadvisor

    A606FAroberth · May 2023

    Learn wine basics and view Tuscan country side

    Fantastic your. Tour guide Mattia a fountain of knowledge and could explain principles of wine in simple terms using analogies as well as cmemistry. Learmed so much. Scenery, especially around the castle was brilliant. Well fed ans lots of wine tasted. Small grpup of 8 made ot mpre intimate as well.

    via Tripadvisor

    doodly · October 2014

    This is definetely a tour worth doing...

    <p>This is definetely a tour worth doing while visiting the Chianti region! This was the highlight of my weekend trip to Siena. We were escorted to the beautfil village of Castellina by private van, after listening to an interesting take on Chinati wine thanks to our guide. After spending some free time in the village and seeing the main attraction of the medieval tunnel, we departed for Greve where a weekend market was taking place. The tour guide stopped at a beautiful little village and let us take photos. The highlight of the day was eating a delicious home-cooked Italian lunch in a little farm and winery. The Italian couple were amazing hosts and were so passionate about their wine business and the Chianti region. They made the lunch so enjoyable, thank you so much! We then went to a larger winery where we were able to watch part of the harvesting process occur. This was exciting and fascinating to watch. We enjoyed another wine tasting here. This is a tour definetely worth doing when you stay in Siena, but be mindful it's a busy day as you do so much! Thank you for an excellent day out!</p>

    via Viator

    merryberry · October 2014

    It was a wonderful day in the Chianti...

    <p>It was a wonderful day in the Chianti region. Both Castellina and Greve in Chianti are beautiful towns not to be missed. The farm where we had lunch gave you a true and sincere experience of Italian family. I'm surprised that this tour is yet to be rated on Viator.</p>

    via Viator

    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 runs

    Why this scores 65

    The Outty Ranking is a weighted composite. Here is how this experience performed on each component.

    Traveler sentiment (30% weight)86
    Review evidence (18% weight)33
    Booking momentum (14% weight)23
    Value for money (12% weight)96
    Listing quality (10% weight)63
    Local standing (8% weight)57
    Booking flexibility (8% weight)100

    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?

    +

    Prices start at $217 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?

    +

    It holds an Outty Ranking of 65 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 last minute in Siena, and how flexible the cancellation terms are.

    Can I cancel or reschedule Small-Group Arezzo and Cortona Day Trip from Siena?

    +

    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?

    +

    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?

    +

    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?

    +

    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?

    +

    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?

    +

    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, Siena: A Wine Tour and Tasting Experience, Small-Group Montepulciano and Pienza Day Trip from Siena. 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?

    +

    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?

    +

    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?

    +

    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.

    What is included in Small-Group Arezzo and Cortona Day Trip from Siena?

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    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; and Lunch. Not included: Hotel pickup and drop-off; and Gratuities. Always check the voucher for the final list before you travel.

    Where is the meeting point for Small-Group Arezzo and Cortona Day Trip from Siena?

    +

    meet tour guide under the large tree that is in front of the church steps Hotel pickup is not included, so plan your own transport and arrive 15 minutes early.

    What languages is Small-Group Arezzo and Cortona Day Trip from Siena offered in?

    +

    It runs in English. Pick your language when choosing a date and time, as not every departure runs in every language.

    Will I get instant confirmation and a mobile ticket for Small-Group Arezzo and Cortona Day Trip from Siena?

    +

    Confirmation is sent by the operator after booking, usually within 48 hours; if it is not confirmed you are not charged. Mobile tickets are accepted, so you can show the voucher on your phone.

    What happens to Small-Group Arezzo and Cortona Day Trip from Siena if the weather is bad?

    +

    It generally runs rain or shine, so dress for the forecast in Siena. Standard cancellation terms apply: free cancellation up to 24 hours before the start.

    What do travelers say about Small-Group Arezzo and Cortona Day Trip from Siena?

    +

    Across 6 reviews averaging 5.0 out of 5, recurring themes include food and drink, the guide, knowledge and storytelling. The tastings and food stops are a highlight for most reviewers.

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