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If you're looking for a fun and curious way to visit Arezzo, you've come to the right place! With this digital guide created with the support of a local, you will be able to visit all the most important monuments at your own pace. You'll get to know the stories and curiosities of Arezzo! But also you will discover everything about local foods, Italian Aperitivo in authentic local restaurants, and much more!
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Arezzo Walking Tour with Audio and Written Guide by a Local
3 to 4 hours
Free Cancellation
4.4
(16)
5% savings
from
$7
$7
Price varies by group size
Member Pricing
Discover the iconic Tuscan town of Cortona (made famous in the book by Frances Mayes "Under The Tuscan Sun"). Located between Florence and Rome, Cortona is rich in Etruscan roots. Cortona is an easy city for everyone to really love. This is because of its atmosphere, its Etruscan past, its delightful medieval old town and also its splendid panoramas.
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Cortona private walking Tour
2 hours 30 minutes
Free Cancellation
5.0
(10)
5% savings
from
$177
$168
Price varies by group size
Member Pricing
This e-bike tour around Cortona offers a unique and engaging way to explore Tuscany's stunning landscapes and rich history, featuring stops at Villa Bramasole, Fortezza del Girifalco, and the Basilica of Santa Margherita. The tour provides an immersive cultural experience, with insider insights from a knowledgeable local guide who shares fascinating stories about the area. Perfect for adventure seekers and families with children, the e-bike allows you to navigate Cortona's charming streets and hilly terrain effortlessly, ensuring you experience the best of the region’s natural beauty and architectural wonders. This tour promises memorable encounters with local traditions, offering a deeper connection to the enchanting town of Cortona.
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Half Day Tour by Ebike Around Cortona
2 to 4 hours
Free Cancellation
5.0
(22)
5% savings
from
$174
$165
Member Pricing
Discover Cortona, the town made famous by the novel Under the Tuscan Sun, during a prvate walking tour. With a local guide, you’ll hear fun facts about the book and the film as you stroll through the Roman square of Piazza della Repubblica and see landmarks such as Teatro Signorelli and the Palazzo Comunale. Choose between a morning or afternoon tour when you book.
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Cortona Private Guided Tour
2 hours
Free Cancellation
4.6
(27)
5% savings
from
$302
$287
Per group
Member Pricing
Olive oil is one of Tuscany's premier products, with a rich history and deeply rooted traditions. Take a deep dive into olive oil culture at SuprEvo, the unique olive oil mill and museum set near Arezzo. Learn how olive oil has been produced over the ages via multimedia exhibits and interactive displays, marvel at historic tools, visit a modern olive oil mill, and sample different oils with a guided tasting. Come away with a better understanding of this important Tuscan specialty, as well as purchases from the olive oil-themed shop.
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Oil museum and oil mill in Tuscany: tour and tasting
1 to 2 hours
Free Cancellation
4.8
(22)
5% savings
from
$23
$22
Member Pricing
Tuscany produces one of Italy’s flagship wines: Brunello di Montalcino. Exploring the countryside where these wines are produced, however, means navigating confusing rural roads and searching for remote wineries. With this wine tour, leave the hassle of driving to the experts and instead enjoy a stress-free day of wine tasting and sightseeing. Visit two winereis and a cellar.
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Brunello and Montepulciano Wine Tour from Cortona
6 to 8 hours
Free Cancellation
4.7
(26)
5% savings
from
$580
$551
Price varies by group size
Member Pricing
In the cellar, in Mugliano, we offer the opportunity to taste our organic products combined with cutting boards made with local products in the different locations present, from the "Garden" to the "Barricaia", to the "Wine Rooms". The wine cellar and the garden atmosphere will guarantee the wine enthusiast a special experience.
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Private Tasting of Organic Wines in the Cellar in Mugliano
2 hours
Free Cancellation
4.7
(11)
5% savings
from
$35
$33
Member Pricing
We are going to do a walking tour of the city visiting the most attractive places and views from the city to the valley around. Starting from the beginning of Cortona, we are going to discover the main street, the most important Churches of the town and the Etruscan walls hidden in Cortona. Walking around 3000 years of History together.
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Walking Tour in Cortona
1 hour 30 minutes
to
2 hours
Free Cancellation
4.5
(24)
5% savings
from
$58
$55
Member Pricing
Discover the rich flavors of Tuscany on this immersive food and wine tour. Begin your day at a family farm in Pienza, renowned for its pecorino cheese, where you'll explore the grounds and enjoy a cheese tasting featuring six varieties, along with homemade accompaniments. Next, savor a delightful three-course lunch paired with Brunello wine in Montalcino, and take a guided tour of the vineyard and aging room. Conclude your adventure in Pienza, heritage UNESCO with a breathtaking view from the town - Explore a family farm in Pienza, the heart of pecorino cheese - Enjoy a tasting of six cheeses with local products and wines - Indulge in a three-course lunch paired with Brunello in Montalcino - Visit the medieval underground city of Montepulciano with a wine tasting
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Pecorino Cheese and Brunello Tasting Tour in Tuscany
9 hours
Free Cancellation
5.0
(10)
5% savings
from
$383
$364
Member Pricing
Discover Arezzo your way with Ciceru’s self-guided walking tour—audio and text in 7 languages, right on your phone. No app, no hassle—just press play and explore! Walking through the streets of Arezzo is like stepping back in time. Be enchanted by the frescoes of Piero della Francesca, the grandeur and splendour of the Duomo and the wonder of Piazza Grande. Arezzo is the ideal destination for a short trip between nature, art and good food!
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Arezzo Interactive City Tour
2 hours
Free Cancellation
2.0
(1)
5% savings
from
$8
$8
Member Pricing
If we talk about Tuscany, we cannot ignore the culture linked to tradition and history: the proposed activity is one of a kind, and interesting, since it allows access to a symbolic place of the valley that would otherwise not be possible to visit. Podere degli Olmi is the only original Leopoldina house that can be visited, and since it is private, access is only possible through this experience. The guide will be the descendant of one of the oldest noble families, who will tell you every detail of the Valdichiana and its traditions. You will take a leap back a few centuries, and it will be interesting to be in the presence of objects and walls full of history and years. The visit will end with a tasting of typical products linked to the territory, the history and cultivation of which will be illustrated to you, so that you can spend an evening learning about the secrets and nature of the territory that hosts you: the Valdichiana.
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Private visit to the House of Grand Duke Leopold of Tuscany with invitation
2 hours 30 minutes
Free Cancellation
5.0
(2)
5% savings
from
$46
$44
Price varies by group size
Member Pricing
This is not simply an e-bike tour — it is a curated private experience for travelers who value authenticity, comfort, and true local elegance. Set among the timeless landscapes of the Val di Chiana and Cortona, the journey unfolds at a relaxed pace, allowing you to connect deeply with the territory rather than simply pass through it. Carefully selected panoramic routes avoid crowds, offering breathtaking views, silence, and the true rhythm of Tuscany. Effortless riding is ensured by premium-quality e-bikes with all modern comforts, while your **certified local guide** shares authentic insights, history, and storytelling, offering a genuine perspective of the region with refined attention to detail. Designed for couples, families, and discerning travelers seeking privacy and quality, this is an intimate and elevated way to discover Cortona — immersive, seamless, far removed from ordinary group tours, and tailored for each guest
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Cortona E-Bike Scenic Ride - Private Medieval Countryside tour
3 to 4 hours
Free Cancellation
5.0
(11)
5% savings
from
$324
$308
Member Pricing
This e-bike tour starts from the historic center of Citta' di Castello, to reach Montone classified among "Most Beautiful Villages in Italy". The approximately 45 km long route can be tackled by all people with basic level of supported training of our pedal assisted bikes. We will follow the banks of the Tiber river a totally traffic-free path until we climb the gentle hills that lead to Montone. Here you leave your bikes we will discover the medieval village with a suggestive view of the Tiber Valley. On request it will be possible to visit the Montone Museum inside the magnificent Cloister of San Francesco where paintings and art objects from the history of Umbria are kept. After the visit we will take the Tiber cycle path back to the starting point in Citta' di Castello
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E-Bike tour in Montone with visit to the medieval village
4 hours 30 minutes
Free Cancellation
5.0
(1)
5% savings
from
$151
$143
Member Pricing
Walking through the medieval streets of Arezzo is a unique experience. Tradition, history and beautiful landscapes to photograph. Arezzo offers all this and much more. The tour aims to show the truest Tuscany, far from the classic tourist routes. Booking a day in Arezzo allows you to relax in one of the most beautiful medieval cities in Tuscany.
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Private and Guided Walking Tour of Arezzo City of Gold
2 to 3 hours
Free Cancellation
5.0
(1)
5% savings
from
$255
$243
Per group
Member Pricing
It’s an incredibile experience that will take you to learn not just local history but culture keys to entry deeply inside the Italian style of life
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Castiglion del lago, Spello & Assisi tour
8 hours
Free Cancellation
4.8
(10)
5% savings
from
$255
$243
Member Pricing
Tasting with the senses: a sensory experience that will accompany enthusiasts to the cellar to learn about how our Syrah is born and to savor its peculiarities. An all-round gustatory embrace that leads us to welcome, by reservation, small groups of enthusiasts, from two up to a maximum of eight people.
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Wine Tasting: a SYRAH that makes you fall in love
2 hours
Free Cancellation
5% savings
from
$35
$33
Member Pricing
Everyone loves Cortona, because it is an authentic and fascinating place. Village of Etruscan origin with stone houses, which stands in the center of an impeccable countryside, hand-sculpted in every corner, pampered by man in every detail. All around there are cypresses, vineyards, olive trees, oaks and fruit trees. Frances Mayes, the very famous writer, made Cortona famous in the eyes of the world thanks to her novel "Under the Tuscan Sun" and the beautiful film based on her novel. So what will we see in this treasure chest of wonders? 1) The Palace of the Captain of the People and the Town Hall, buildings from the medieval era 2) Piazza Signorelli, which owes its name to the famous Renaissance painter who was a friend of Leonardo da Vinci. 3) Piazza del Duomo with its fourteenth-century gothic cathedral 4) the Girifalco Fortress 5) The ancient walls of Cortona with the Porta Bifora, the oldest, as it is of Etruscan origin Enjoy strolling through magic Cortona!
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Cortona Private walking Tour under the Tuscan sun
2 hours
Free Cancellation
5.0
(3)
5% savings
from
$219
$209
Price varies by group size
Member Pricing
Tuscany is one of the most beautiful areas in Italy, with lots of spots to take magical photographs. I will create magical memories through the photos for you to keep forever. Exploring the famous and hidden gems together will be great!
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Tuscany Private Photoshoot Experience
2 hours
Free Cancellation
5.0
(231
Operators
)
5% savings
from
$894
$850
Per group
Member Pricing
Explore the enchanting city of Arezzo on our private kid-friendly tour designed to captivate the imagination of the whole family! Our adventure begins at the picturesque Piazza Grande, the heart of Arezzo, where you will be amazed by the medieval architecture and the lively atmosphere. Next, we will marvel at the imposing Medici Fortress and the Duomo from the outside. One of the highlights of our tour is the entrance to the Archaeological Museum of Gaius Mecenas and the adjacent Roman Amphitheater. Here, kids will have the chance to uncover the mysteries of ancient Rome through interactive exhibits. Additionally, fans of the beloved movie "La Vita è Bella" will delight in spotting the iconic filming locations throughout the city, adding a touch of cinematic magic to our journey. Join us for an unforgettable 2.5-hour adventure in Arezzo, where history, culture, and fun come together to create lasting memories for the entire family!
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Kid-Friendly Arezzo Private Guided Tour for Families
2 hours 30 minutes
5% savings
from
$265
$252
Price varies by group size
Member Pricing
I was Born and raised in this magical region od Tuscany, I have key villagers that I have known for many years and you know in Italy is all about relationships...I go above and beyond to take care of my clients. One thing that makes me unique is that I have lived abroad for several years and my spoken English is excellent, this is very important for you to maximize your tour and investment, I comunicate well and I know how to relate to the culture overseas. One other thing is I can sure teach you history but what my clients love about me is the stories and secret I tell them and one thing is for sure...you will laugh and not be the usual boring tour!!!!!
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Val D'Orcia Dreaming!!
4 hours
Free Cancellation
5.0
(20)
5% savings
from
$228
$217
Member Pricing
Get to know an Italian family by dining with them in their home. Take the stress out of finding a restaurant by booking this private dinner for an intimate experience of Italian cuisine and culture. You and your group will enjoy a delicious three-course meal paired with local wine. Sample delicacies like tiramisu and pasta dishes made using fresh ingredients from their garden.
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Typical Tuscan family dinner in a Villa near Cortona
3 hours 30 minutes
Free Cancellation
3.7
(3)
5% savings
from
$79
$75
Member Pricing
Tuscany is famed for its scenery and gastronomy, but navigating this rustic region isn’t easy—especially for first-time visitors. Enjoy a deluxe introduction to the rolling Tuscan landscape during this full-day tour of Cortona and Montepulciano. A heart Tuscan lunch is included, plus a guided tour of a historic wine cellar and five exclusive wine tastings.
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Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings
8 hours
Free Cancellation
5.0
(45
Operators
)
5% savings
from
$302
$287
Price varies by group size
Member Pricing
Born from a "dream of love and an idea of beauty", Pienza, the ideal city of the Italian Renaissance, is still today an intact testimony of an illustrious architectural project, commissioned by Pope Pius II Piccolomini and made concrete by the great Florentine architect Bernardo Rossellino. Built in a very limited period of time (1459-1462), the city of Pio is the result of a single master plan marked, by the will of the great humanist pope who gave it the name, by design criteria of harmony and aesthetic perfection still today. clearly visible in the small urban center that was Corsignano in the Middle Ages.
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Private Guided Tour of Pienza on Foot
3 hours
Free Cancellation
4.7
(7)
5% savings
from
$244
$232
Per group
Member Pricing
A private professional photo and video experience in the Val d’Orcia, designed for elegant and authentic visual memories. I personally guide you through the most iconic locations starting from Pienza, selecting the best light and cinematic angles to create natural, high-quality photos and videos. What’s included: – 30 professionally edited photos – 1 cinematic video trailer (approx. 2 minutes) with professional editing and color grading – Video delivered in both 16:9 and 9:16 formats – Professional equipment and aerial drone footage (where permitted) – Digital delivery via email within 3 days
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Private Luxury Photo and Video Shoot in Val d'Orcia
2 to 4 hours
Free Cancellation
5% savings
from
$580
$551
Per group
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Must-Dos in Arezzo
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Prada Outlet
Explore Options
from
$165
Arezzo Piazza Grande
Explore Options
from
$143
Villa La Ripa
Explore Options
from
$66
Basilica of San Francesco
Explore Options
from
$165
Pienza
Explore Options
from
$45
Santa Margherita Basilica (Basilica di Santa Margherita)
Explore Options
from
$163
Prada Outlet
Explore Options
from
$165
Arezzo Piazza Grande
Explore Options
from
$143
Villa La Ripa
Explore Options
from
$66
Basilica of San Francesco
Explore Options
from
$165
Pienza
Explore Options
from
$45
Santa Margherita Basilica (Basilica di Santa Margherita)
Explore Options
from
$163
Prada Outlet
Explore Options
from
$165
Arezzo Piazza Grande
Explore Options
from
$143
Villa La Ripa
Explore Options
from
$66
Basilica of San Francesco
Explore Options
from
$165
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