Top Arezzo Day Trips

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.

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.

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.

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.

Swap the cobbled streets of Cortona for its surrounding countryside on this small-group e-bike tour—and cover plenty of ground with ease. Follow the winding Tuscan roads through the Val di Chiana with views of vineyards and cypress-lined hills. A local guide leads the way and adjusts the route based on the group, stopping at a boutique winery where an optional wine tasting and lunch are available.

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.

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.

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.

Explore the charming Tuscan village of Lucignano on an exhilarating eBike tour that takes you through picturesque landscapes and hidden gems only locals know. Visit historic landmarks, lush vineyards, and stunning viewpoints, all while enjoying the ease and fun of electric biking. Afterward, immerse yourself in the rich culinary traditions of the region with a hands-on cooking class led by a local chef. Learn how to make the most famous shape of pasta in the area: PICI! Perfect for adventure seekers, food enthusiasts, and families, this tour offers a unique blend of outdoor adventure and authentic cultural experiences that will leave you with unforgettable memories of Tuscany.

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.

Optimize your logistics and make the most of your time with this private transfer from Florence to Assisi that includes stops to visit the Tuscan hill towns of Montepulciano and Cortona. Enjoy the ease of pickup at your Florence hotel and explore towns worry-free while your driver stays with the vehicle and your luggage. Sightsee, shop, and dine at your own pace, then end your day with seamless drop-off directly at your Assisi hotel.