Top Arezzo Sightseeing 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.

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.

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 Cortona on a private, fully curated luxury e-bike journey blending breathtaking Tuscan landscapes, culture,and authentic local experiences.Ride premium e-bikes along serene, scenic routes with a professional local expert who brings the region to life with stories, history, and insider knowledge far from crowded paths.Pause to admire charming corners and hidden views, feeling the rhythm of the rolling hills and medieval streets. The journey culminates at a refined, private winery where the owner welcomes you for a curated Tuscan lunch with no overlapping. Savor seasonal appetizers highlighting the finest local products, a thoughtfully prepared first course, dessert or gelato and coffee,paired with at least three glasses of Syrah from different vintages to reveal depth and character.Designed for couples, families, and discerning travelers, this is a seamless, immersive, and unforgettable way to experience Cortona—where every detail is crafted for comfort, privacy, and discovery.

Embark on a private, guided journey through the picturesque vineyards and historic cellars of Montepulciano, the home of the celebrated Vino Nobile di Montepulciano. This exclusive tour offers an immersive experience that captures the essence of Tuscan winemaking tradition. What to Expect Guided Visits to three renowned Wine Estates: Explore estates with centuries of winemaking expertise. Learn about the intricate process of crafting Vino Nobile di Montepulciano from passionate experts. Exclusive Wine Tastings: Savor a curated selection of exquisite wines at each estate. Lunch at the Second Estate: Indulge in a traditional Tuscan meal paired with exceptional wines. This intimate experience blends Tuscan culture, history, and gastronomy into a memorable day amidst the stunning countryside of Montepulciano. Whether you're a wine enthusiast or simply looking to enjoy a luxurious day in Tuscany, this tour is the perfect choice.

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.

Explore Lake Trasimeno on an e-bike tour. Ride through a natural landscape, stop at Punta Navaccia for birdwatching, and visit the fortified town of Castiglione del Lago. Begin your journey at Passignano dul trasimeno and cycle along the lake's shore. Enjoy the natural surroundings, far from the hustle and bustle of city life, as you pedal on a mostly unpaved bike path. Reach Punta Navaccia, a significant natural site dedicated to birdwatching. As you cycle through a wilder area of the lake, keep an eye out for free-roaming animals. Arrive at Castiglione del Lago, a charming fortified town, and take a relaxing break at one of the many lakeside cafes. After your break, continue your ride back to the starting point, completing your scenic loop around Lake Trasimeno. - Guided tour of 56 km, suitable for groups of 4 - 8 people - Includes e-bike and helmet rental - Possibility of Wine Tasting and Typical Products by Reservation

Kick off your day with a comfortable ride through the stunning Tuscan countryside. First, we’ll arrive in Siena, one of Tuscany’s most beautiful towns. Explore Piazza del Campo, famous for the Palio di Siena horse race, admire the breathtaking Duomo (Cathedral), and wander through the charming, narrow streets of the historic center. Wine Tasting & Light Lunch Next, we’ll head to a renowned winery for a light lunch paired with an amazing wine tasting experience. A sommelier will guide you through five exceptional wines, plus an olive oil tasting. After lunch, we’ll continue our journey with a spectacular drive through the rolling Vernaccia di San Gimignano vineyards, home to Tuscany’s most famous white wine. Stop in San Gimignano you’ll have free time to explore this medieval gem, known for its 14 towers dating back to the 13th century. The town’s atmosphere will transport you back to the Middle Ages! And of course, you can’t miss the world’s best gelato at Gelateria Dondoli.

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.

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.

The rolling hills of Tuscany make it a great spot to explore using a motor-assisted e-bike. On this full-day private tour, get picked up at your Florence hotel and delivered to the countryside. Discover the town of Pienza—a UNESCO World Heritage Site—and enjoy an outdoor lunch of authentic local produce, including some wine, before heading off to relax by Bagno Vignoni’s ancient thermal springs.

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.

A tour where you can appreciate the beauty of the Umbrian High Tiber and its traditions. You will have at your disposal brand new e-bikes with which it will be possible to reach in the same tour the medieval villages of Citerna and Anghiari. A licensed National Guide will lead the tour in Italian or English presenting the most interesting aspects of the historical and natural heritage of the valley. We will cross the historic center of Citta' di Castello to follow the pleasant cycle path of the Tiber river until we reach Citerna. After a short visit we will resume the route to Anghiari.

Experience the magic of Tuscany without the sweat! Join us for a half-day e-bike adventure through the rolling hills surrounding the “Ideal City” of Pienza. This tour is carefully designed to take you along the most iconic white roads (strade bianche) in the region, offering panoramic views that look like they’ve been pulled straight from a postcard. Tour Highlights: Effortless Riding: Glide up the Tuscan hills with ease thanks to our premium electric bikes. Iconic Landmarks: Cycle past the famous Gladiator Row (Cipressi di San Quirico) and the charming Vitaleta Chapel. Cinematic Views: Capture the breathtaking landscapes of the Val d’Orcia, a UNESCO World Heritage site. Local Culture: Start and finish in the Renaissance gem of Pienza, with plenty of tips on where to find the best Pecorino cheese or best restaurants.

Brunello di Montalcino is one of Italy's most prestigious wines, but navigating to the rural wineries outside of Montalcino on your own can be stressful. On this private wine tour, let your driver take the wheel and focus on vineyard views as you make your way to the top wine estates and cellars for exclusive tasting experiences. Explore stunning vineyards, learn about traditional winemaking techniques, and savor the rich flavors of Tuscany with guided tastings and a traditional lunch.

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

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 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.

Put a professional touch on your Tuscany vacation photos, and book a day-long photo tour with an award-winning photographer at your side. Created and led by the talented Marco Bulgarelli, the tour takes you to impressive vantage points around Val d'Orcia and the Siena province where gorgeous shots are guaranteed every time.

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.

Take a break in the countryside with a private tour that includes visits to boutique wineries and a sustainable, family run cheese farm. Enjoy a full day dedicated to wine and cheese, exploring the heart of Tuscany. Drive through the Val d'Orcia, a UNESCO World Heritage Site, and savor some of the region’s finest red wines, including Vino Nobile di Montepulciano and Brunello di Montalcino. Stroll through the medieval squares of Pienza and sample authentic Tuscan cheeses at a historic estate, featuring one of the most breathtaking terraces overlooking the Orcia Valley.