Top Arezzo Tours by Duration

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.

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.

This exclusive private wine tour takes you from Cortona to the heart of the Chianti Classico Black Rooster, an iconic wine area rarely reached from this part of Tuscany. Travel in comfort with a local professional driver and enjoy a personalized journey through one of Tuscany’s most celebrated wine landscapes. The experience includes visits to three carefully selected Chianti Classico DOCG wineries, where you will enjoy guided cellar tours and premium wine tastings. Each winery offers a different perspective on the Black Rooster tradition, allowing you to discover the diversity, history, and craftsmanship behind authentic Chianti Classico wines. A traditional Tuscan lunch is included, perfectly paired with local wines and seasonal products, for a complete and immersive Chianti experience. Designed for travelers seeking authenticity, privacy, and high-quality wine experiences, this tour combines culture, scenery, and exceptional flavors in a relaxed and exclusive setting.

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.

Discover the world-famous flavors of Tuscany on a 6-day culinary experience in Abrezzo. Stay at a private villa with a pool, where you can make friends with other aspiring chefs and soak up the Mediterranean sun. Learn to cook time-tested recipes for soups, sauces, pastas and desserts under the guidance of a professional chef, and enjoy many freshly prepared meals in the gorgeous setting. Visit a local winery and the charming villages near Abrezzo, and savor regional cuisine at local trattorias.

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.

This isn’t just a vacation — it’s an immersive Tuscan journey where you’ll: Taste Italian cuisine and recipes passed down through generations. Wander cobblestone streets in Cortona and beyond Indulge gelato daily. Share sunsets over rolling hills with friends and family.

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.

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.

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!!!!!

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.

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.

Book for an unforgettable cycling experience in Tuscany — carefully designed routes, top-quality equipment, and private tastings in authentic local settings.