Top Arezzo Historical Tours

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.

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!

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.

Discover the most popular landmarks and best kept secrets of Arezzo on a 2-hour private walking tour. The short jaunt around the historic center is the perfect way to orient yourself to the Tuscan city for future exploring. Highlights include the Parish Church, Piazza Grande, Antique Market, and more. Be sure to ask for recommendations for things to see, do, and eat during the rest of your vacation.

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.

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.

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.

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

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

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.

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!

During this 2-hour private tour, your expert guide will lead you through the most important and interesting sites of the beautiful city of Arezzo. You will be able to admire the medieval city and visit its historic shops.

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

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!

Ride through the rolling hills of Pienza’s countryside on a private e-bike experience, discovering charming landscapes and historic villages. After the ride, step by step, visit a working mill where your guide will show the journey from wheat to fresh pasta, sharing local stories, traditions, and insights into Tuscan culture, wine, gastronomy, and the region’s vineyards. Glide through vineyards and golden fields in the heart of UNESCO-listed Val d’Orcia, near Montalcino, enjoying cinematic views, iconic cypress-lined roads, and hidden gems beyond usual sights. With TREK e-bikes and carefully chosen routes, the journey unfolds at a relaxed pace, letting you explore far from crowds. The tour concludes with a light Tuscan lunch in a special setting beside a castle, offering a final gastronomic moment highlighting the region’s culture, flavors, beauty, and local craftsmanship — an immersive Tuscan journey for travelers seeking authenticity, refinement, and true Tuscan elegance.

This experience follows the same high-level luxury format offered in Cortona, reimagined in Montepulciano and the Chiana Valley. Set among Tuscany’s rolling hills, the journey unfolds at a relaxed, immersive pace. Premium Trek e-bikes carry you through vineyards, olive groves, and medieval villages. While Cortona shows refined hilltown elegance, this experience reveals Tuscany’s authentic, expansive soul—quiet country roads, hidden corners, and timeless rhythms. Discover Tuscany’s hidden gems, panoramic vineyards, and medieval villages on a private, immersive tour designed for lasting memories. Led by a certified guide, you explore not just the landscape, but its history, traditions, and soul. As in every Hero-format experience, the journey concludes with a carefully selected lunch, a moment of reward, connection, and authentic Tuscan hospitality. Private, seamless, and deeply personal—where luxury is measured in meaning, not excess, and every ride becomes a lasting memory.

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

Optimize your logistics and make the most of your time with this private transfer from Florence to Assisi that includes stops to visit the Tuscan hill towns of Montepulciano and Cortona. Enjoy the ease of pickup at your Florence hotel and explore towns worry-free while your driver stays with the vehicle and your luggage. Sightsee, shop, and dine at your own pace, then end your day with seamless drop-off directly at your Assisi hotel.

Immerse yourself in Tuscany’s culinary heritage with a hands-on pasta-making class. Create colorful tagliatelle and ravioli from scratch, enjoy a three-course meal with bruschetta, Chianti wine, and seasonal dessert. Take home recipes and an apron as mementos.

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!!!!!

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.