Top Arezzo Walking Tours

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!

You will visit with us our winery and vineyard to discover our philosophy and passion. A unique experience in which you can then taste 4 wines from Villa La Ripa, paired with excellent products from the Tuscan tradition in a light three-course lunch. You can also enjoy a wonderful view from the tasting room overlooking the winery and the vineyards of the company.

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!

You will understand how vast and interesting the world of oil is. The walk extends over two gentle hills covered with olive trees. The view is over the entire Val d'Orcia and the tasting takes place in total contemplation of what surrounds you

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.

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.

Make the most of your time in Montepulciano with this walking tour that takes in the highlights of the medieval hill town in just hours. Skip the dry guidebook and visit with a guide who can make the Tuscan town’s history to life as you stroll the picturesque lanes and climb to the top of the bell tower (own expense) to admire the views. End with a glass of local wine to cap off your visit.

Arezzo gave the world Petrarch and Vasari — and its medieval streetscapes are as good as anything in Tuscany. This app-led scavenger hunt takes you through Arezzo on foot, with phone-based riddles leading from one landmark to the next. No guide, no fixed start time. • Follow clues to the Chiesa di Santa Maria della Pieve, the Chiesa di San Domenico, and Palazzo Pretorio — three landmarks anchoring one of central Italy's finest medieval centres • Fully self-paced with no time limit — start straight from the train and take it at your own speed • Works for couples, families, and friend groups; observation tasks and photo challenges keep all ages engaged Around 2 hours, any group size, available in English and Italian. Arezzo hosts the Joust and the antiques market on the Piazza Grande — the trail gives you the city in between.

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.

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.

During our visit we will discover everything about the past of this wonderful town, known as the "ideal city". We will talk about its origins and the way it was turned into a beautiful Renaissance city, mostly thanks to the efforts of the Pope Pius II. Not only will we discover every secret (Is the shape of the main square trying to send a hidden message? What happens twice a year?), but we will also go and look for the best corners and panoramic spots where to take great pictures. Last but not least, we won't leave Pienza without tasting its typical and super tasty Pecorino cheese! IMPORTANT: the tour schedule in the system is 10am and 15pm, but the tour times can be arranged directly with the guide upon request.

Head to an authentic family-run vineyard and winery near the walled town of Castiglion Fiorentino to discover Tuscan wine-making traditions on this private tour. Explore the vineyard (weather permitting), the cellars, and the Vin Santo production area as you hear about the techniques the family has used for generations. Wrap up with a tasting of cheese, salami, extra virgin olive oil, and six different wines.

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.

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.

A true paradise nestled in the Tuscan hills where once stood a temple dedicated to the mythological hero Hercules. We are in Val di Chiana, a production area of Chianti, a land of excellence that offers scenic wonders, where the winemaking tradition is expressed at the highest levels. We produce wines with a Tuscan soul, thanks to the passion for wine and the love for our territory that accompany the entire production process. We offer exclusive packages to visit our estate with expert guides and live a unique experience. The strategic position of Camperchi, just 5 minutes from the A1 Monte San Savino motorway exit, offers the opportunity to discover the wonders that Tuscany and Umbria offer

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!

See Tuscany’s loveliest scenery, and discover the history of one of Italy’s most revered wines, on this private, half-day tour. Following pickup from your area hotel, head off the tourist trail to a local, family-owned winery. Taste Brunello di Montalcino—a 100% Sangiovese wine that’s one of Italy’s best—as well as other wines and nibbles. You’ll also tour the idyllic Val d’Orcia, from ancient hill towns to historic monasteries.

Discover the charm of Cortona on our kid-friendly tour designed to engage and entertain the entire family! This enchanting adventure begins with a visit to the Basilica of Santa Margherita to admire the stunning architecture and frescoes. Next, we head to the Belvedere, offering breathtaking views of the surrounding Tuscan landscape that will captivate both young and old. It's the perfect spot for family photos and a moment of awe. Our journey continues to Piazza della Repubblica, the vibrant heart of Cortona's old town. We will then explore the charming old town, wandering through its picturesque streets and uncovering hidden gems along the way. The tour includes an external view of the magnificent Cathedral of Santa Maria Assunta, an architectural marvel that adds to the town's rich historical tapestry. Book an unforgettable 2-hour family adventure in Cortona, where history, culture, and fun combine to create lasting memories for everyone!

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!

Enjoy a wine tasting experience in an ancient villa located in Valdichiana in the heart of Tuscany. Wander the vineyard and admire the amazing Tuscan landscape. Learn about the history of the location and get an explanation about the methods and techniques of wine production. During the experience, taste three Tuscan wines as a professional sommelier explains the particularities of the wines.

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.

Perfect for families, couples, and solo travelers who want to enjoy the peace of the Tuscan countryside, where fresh air replace the city's summer heat. Here what makes it special: Real Truffle Hunt: a 50-minute walk through the woods, learning the secrets on how to find fresh truffles in their natural environment. Hands-On Cooking Class: Make fresh pasta & classic Italian tiramisu from scratch, using top-quality ingredients. Traditional recipes are revisited with the unique flavor of truffle. Gourmet 4-Course Lunch: Enjoy a truffle-based meal featuring what you’ve prepared, with one bottle of local wine for every two guests, served in a charming rural setting. Stunning Location: Set at Tenuta Armaiolo, a historic estate surrounded by wild nature, olive groves, and rolling hills. The atmosphere is timeless and peaceful. Social & Unforgettable: A chance to relax, connect, and experience something truly unique—perfect for meeting people, learning, and enjoying authentic Tuscany.