Top Arezzo Sightseeing Tours in 2026

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.

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.

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 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

Embark on a 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.

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!

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.

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!

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.

Once the tour is booked, you can go to the rental point to pick up the bicycles and start the experience with virtual navigation. The e-bike loop tour starts in Pienza and measures about 26 km with 350 m of positive elevation gain: medium-easy level. The route alternates secondary roads, paved sections, about 6 km of state road, and short paths. Some sections are open to vehicular traffic and it is therefore important to have good confidence with the bicycle and feel safe on shared roads. The itinerary crosses the landscapes of Val d'Orcia among estates, open fields, and panoramic viewpoints, also passing near a famous location from the film Gladiator. The main stop is Bagno Vignoni, a thermal village famous for the large water basin in the center of the square. During the return towards Pienza, the route passes near the Cappella di Vitaleta. The road alternates between asphalt, secondary roads, dirt roads, and short easy gravel paths.

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.

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.

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.

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.

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 Cortona through an exclusive private journey for travelers seeking the highest level of authenticity and comfort. Ride premium e-bikes along quiet panoramic routes guided by a local expert who shares stories, culture, and hidden perspectives of Tuscany.Enjoy privileged access to a family-owned olive oil estate dating back to the 1800s, where a private visit reveals traditional production methods, historic tools, and centuries of heritage rarely experienced by visitors. Conclude the day with a refined winery experience with a curated lunch and exceptional wines in an intimate setting, with no overlapping groups.As a final gesture, guests receive a personally selected bottle of estate olive oil — a lasting memory of Tuscany. Designed as a fully private experience, every detail is tailored to create rare access, genuine connection, and unforgettable moments.Ideal for travelers who prefer meaningful experiences over crowded tours and value time, privacy, and true Tuscan elegance.

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.

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!

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 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

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.

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.

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.