Top Arezzo Sightseeing Tours

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, 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 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.

Explore Tuscany and savor the wines of the region on this private all-day tour. Visit the medieval cities of Montepulciano, Pienza, and Montalcino and discover historic cellars. Enjoy wine tastings with a light lunch, then head to Pienza, where Pecorino cheese is made. Stop in Montalcino to see the castle and visit a winery where you’ll taste Brunello di Montalcino, one of Italy's most prestigious wines.

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.

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.

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.

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.

Experience the breathtaking Chianti hills on a day trip filled with stunning landscapes and rich culture. Begin with a visit to the UNESCO-listed city of Siena, renowned for its exquisite architecture. Enjoy a delicious lunch at a traditional Tuscan farmhouse, featuring homemade pasta and five tastings of the finest Chianti wines. Then, discover the secrets of local wine production in a picturesque setting.

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.

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.

Leave the hustle and bustle and tourist crowds of Rome behind for the day on a private tour to Val d’Orcia. This excursion is ideal for travelers seeking an authentic Italian cultural experience but are short on time. Comfortable transportation takes you from the capital city and into the UNESCO-listed valley. There, you’ll enjoy leisurely visits to the Tuscan Renaissance town of Pienza and the medieval town of Montepulciano.

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.

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.

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.

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.

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.

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.

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.

Hosted personally by a local curator specialized in private experiences. Not a tour, but a privately curated day through the hidden treasures of Cortona Valley. Access medieval castle, historic abbey, and secret estates normally closed to visitors, all at a relaxed pace. Along the way, you’ll pick and collect hidden local treasures, from artisanal products to olives and specialty ingredients, later enjoyed with a refined Tuscan wine pairing. Enjoy a private lunch and tasting with a curated itinerary, ensuring no overlapping groups and a premium pickup experience. Every moment is designed to delight your senses and create memories that last. Fully private, each step is carefully crafted to immerse your group in Tuscany’s culture, traditions, and seasonal delights — far from the crowds and tailored entirely to your experience.

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

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.