Arezzo isn’t just a city of stunning architecture and centuries of art—it’s also a fantastic place to explore on two wheels. Thanks to its gentle rolling hills, well-maintained paths, and an abundance of historic sites, biking here becomes more than just exercise; it’s a way to see Tuscany’s authentic side. One of our favorite options is the Cortona – Easy guided eBike tour around the Etruscan City, which combines effortless riding with visits to iconic sites like Villa Bramasole from Under the Tuscan Sun. It’s a perfect introduction to the area’s charm and privacy, with small group sizes ensuring personal attention.
While Arezzo itself offers beautiful cityscapes, the surrounding countryside shines on bike tours. We love the idea of combining scenic rides with wine tasting, which you’ll find in the Cortona – eBike tour and wine tasting in the Val di Chiana, a 5-6 hour experience that mixes cycling through Tuscan vineyards with a delicious wine and food experience. For those interested in exploring beyond, options like the Castiglion Fiorentino eBike tour offer a less crowded, more nature-focused ride, including a visit to Montecchio Castle.
Below, you’ll find a detailed look at each of the top bike tours in Arezzo—covering everything from short city explorations to full-day wine adventures.
1. Cortona – Easy guided eBike tour around the Etruscan City
At number 1 on our list, this easy guided eBike tour in Cortona is a fantastic choice for anyone who wants to explore the scenic hill town without breaking a sweat. It lasts about 2 to 3 hours and covers paved streets, historic routes, and some of the town’s most beloved sights. The tour includes stops at Fortezza di Girifalco, where you can enjoy one of the best views of Cortona, and the basilica of Santa Margherita, with its stunning facade and artwork.
What makes this tour stand out is its small group size—limited to 2 or 3 bookings—to ensure comfort and personalized attention. The bikes are high-quality electric models, making the ride accessible for most fitness levels. The highlight for many is a visit to Villa Bramasole, famous from Under the Tuscan Sun, surrounded by gardens and olive groves. Reviewers love the friendly guides and the flexibility to customize the experience. Priced at $165, it offers excellent value for a rich, relaxed introduction to Cortona’s character.
Bottom Line: A short but sweet ride perfect for those new to e-biking or visitors who want a manageable yet immersive taste of Cortona.
2. Cortona – eBike tour and wine tasting in the Val di Chiana
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Starting from a point 20 minutes by car from Cortona, this full-day eBike and wine experience is ideal for those who want to combine cycling with a deep dive into Tuscany’s viniculture. Over 5 to 6 hours, you’ll pedal through the picturesque Val di Chiana’s rolling hills, passing vineyards, cypress-lined roads, and historic farms. The ride itself is gentle, covering about 32 kilometers with e-bikes available if needed, making it suitable for most fitness levels.
The tour includes a visit to a local winery where you’ll learn about traditional winemaking, followed by tastings of regional wines and local products. The sunset views over the Tuscan countryside are breathtaking, and the relaxed pace allows plenty of time to soak in the scenery. Guests consistently praise the friendly local guides and the delicious lunch that accompanies the wine tastings. For $188.01, this tour offers a wonderful blend of active exploration and culinary indulgence.
Bottom Line: Perfect for wine lovers and those wanting an all-encompassing experience of Tuscany’s landscapes and flavors.
3. Castiglion Fiorentino – eBike tour in the Tuscan countryside
At number 3, this eBike tour in Castiglion Fiorentino provides a 3.5-hour journey into Tuscany’s lesser-known but equally stunning scenery. Starting from Arezzo, you’ll ride through lush, untouched nature with panoramic views, passing by Montecchio Castle—an ancient fortress with a thousand years of history. The ride is well-suited for most levels with manageable terrain and top-notch bikes.
Guided by experienced locals, you’ll learn about the area’s history while enjoying the tranquility of the countryside. The inclusion of a visit to Montecchio Castle adds a historic touch, and the small group size ensures a relaxed, personalized experience. Guests note the helpful guidance and the beautiful scenery, with many saying it’s a wonderful way to escape the crowds and connect with nature.
Priced at around $159.35, this tour offers outstanding value, especially for those interested in combining history and scenic riding.
Bottom Line: An excellent choice for slightly more adventurous riders wanting a mix of history and nature.
4. Pienza – Ebike tour for a full immersion in Val d’Orcia
This full-immersion eBike tour in Pienza is a 3.5-hour journey into the heart of the UNESCO-listed Val d’Orcia. It begins from the charming Renaissance town of Pienza, where you’ll pedal through landscapes that look like they’ve come straight out of a postcard—cypress trees, rolling hills, and fields of wheat and lavender. The tour combines effortless riding with moments to appreciate panoramic views and small local towns.
Guided by a knowledgeable host, you’ll visit notable spots like the Romanesque basilica in Pienza and take in the scenery at every turn. The landscape’s beauty is complemented by insights into local traditions and architecture, making it an enriching experience. Reviewers highlight Roberto’s professionalism and the memorable visits to small towns and natural springs.
For $159, this tour offers a perfect balance of scenery, culture, and moderate activity, making it suitable for anyone wanting a deep dive into the Tuscan countryside.
Bottom Line: A well-rounded, scenic experience ideal for lovers of art, architecture, and nature.
5. CORTONA Medieval Charme: PRIVAT E-bike Experience, Top Quality!
Coming in at number 5, this private eBike experience in Cortona offers a personalized tour lasting about 3 to 4 hours. It’s tailored to your interests, with exclusive visits to Villa Bramasole, the Basilica of Santa Margherita, and the Fortezza di Girifalco. Starting from a scenic belvedere overlooking Valdichiana, your guide will share stories about Cortona’s Etruscan and Renaissance history.
What makes this tour special is its private nature—perfect for couples, families, or groups wanting a more intimate experience. The guide’s extensive knowledge and the carefully curated stops ensure a rich, relaxed exploration. The included visits to Bramasole and Santa Margherita offer cultural depth, and the route’s flexibility means you can focus on what interests you most.
Costing around $311.18, this is excellent value if you’re seeking a customized, in-depth experience with high-quality service.
Bottom Line: Best suited for travelers who want a private, in-depth look at Cortona’s treasures.
6. Bike Ride immersion Val d’Orcia
At number 6, this guided Bike Ride immersion in Val d’Orcia covers approximately 20 miles through the iconic Tuscan landscape. Starting from Pienza, it takes you over rolling hills dotted with vineyards and farms, ending at Bagno Vignoni, a thermal spa town. The ride is straightforward with moderate hills, and e-bikes are available to ease the journey.
What teams up this tour is its focus on authentic scenery combined with a visit to the thermal baths—ideal for those who want a relaxed sightseeing experience with a touch of wellness. Reviewers rave about Panos’ organization and the picturesque views, including a memorable stop at a natural hot spring.
Priced at $138.91 per person, it’s a good value for a full day of scenic riding plus optional thermal relaxation.
Bottom Line: A delightful mix of nature, history, and leisure, perfect for a leisurely rider.
7. Half Day Tour by Ebike Around Cortona
This half-day eBike tour offers a flexible 2 to 4-hour exploration with stops at Villa Bramasole, Fortezza del Girifalco, and the Basilica of Santa Margherita. It’s designed for those short on time but eager to see Cortona’s highlights on two wheels. The route includes a visit to the “Under the Tuscan Sun” farmhouse and a walk through the Etruscan walls.
The tour is praised for its knowledgeable guide and a good balance between sightseeing and riding. It’s suitable for families and adventure seekers alike, with bikes that accommodate different skill levels. The price is around $174.22, offering a quick yet meaningful encounter with Cortona’s sights.
Bottom Line: Great for travelers with limited time who still want a comprehensive taste of Cortona.
8. MONTEPULCIANO: The Heart of Chiana Valley, PRIVAT E-Bike Experience
Ranked 8, this private eBike experience in Montepulciano takes about 3 to 4 hours exploring the scenic Chiana Valley. It starts with a visit to the historic Abbazia Farneta, a 30-minute stop in a centuries-old monastery, and continues through endless vineyards, olive groves, and small villages. A highlight is a visit to a local winery, where you’ll enjoy a guided tasting and a light lunch.
This tour is tailored for those who want an intimate, insider look at Tuscany’s viticulture and rural life. The guide shares stories about the land’s history and traditions, elevating the experience beyond just a bike ride. The cost of $373.20 reflects its personalized nature and includes the winery visit.
Bottom Line: Ideal for travelers seeking a private, wine-focused tour with a deep connection to Tuscany’s land.
9. Around Lucignano Private ebike tour and Cooking Class
For those wanting a full culture, this around Lucignano eBike and cooking class combines a scenic ride with a hands-on culinary experience. Starting in Lucignano, you pedal through scenic countryside, visiting a castle, medieval village, and a sacred sanctuary. The highlight is a cooking class where you learn to make PICI, a traditional Tuscan pasta.
Priced at $650.08, this tour is a more premium option, suitable for food lovers who want to combine active sightseeing with authentic culinary skills. The route includes stops at farms and scenic viewpoints, making it both engaging and educational. Reviewers mention the knowledgeable guides and the memorable meal they prepared.
Bottom Line: Best for travelers who want to incorporate cooking into their biking adventure for a full cultural feast.
10. E-Bike Tour in Montone with Visit to the Historic Winery
Completing our list, this tour from Montone offers about 4.5 hours of cycling through the Umbrian hills. Starting from Città di Castello, it includes a visit to Montone—one of Italy’s most beautiful villages—and a visit to the historic Blasi Cantina for a tasting session in a cellar dating back to 1720.
The route follows traffic-free paths along the Tiber River and climbs gentle hills, making it accessible to most riders. The wine tasting at the end adds a tasty conclusion to the day. Reviewers appreciate the personable guides and the scenery, calling it a well-organized and memorable experience.
At $156.12, it’s a good choice for those interested in combining history, scenic riding, and wine.
Bottom Line: A charming blend of cultural exploration and wine over a manageable route.
How to Choose the Best Bike Tour for You
When selecting your ideal bike tour in Arezzo, consider your budget, fitness level, and interests. For a quick city overview combined with cultural highlights, the Cortona eBike tour is perfect. If you love wine and scenic landscapes, the Val di Chiana wine tasting offers a full day of relaxation and indulgence. Looking for a private, tailored experience? The Cortona private eBike ensures personalized service. Budget-conscious travelers can stick to shorter rides like the half-day tour, while adventurous souls might enjoy combining biking with unique activities such as cooking classes.
Booking early is advised, especially for popular tours or those with limited availability. Also, consider the time of year—spring and early fall typically offer the best weather.
Final Thoughts
Arezzo and its surroundings offer a wide array of bike tours tailored to different interests and levels of fitness. Whether you want a quick cultural spin, a full-day wine and scenery adventure, or an exclusive private experience, there’s something to match your travel style. For a family-friendly option with a gentle ride, the Cortona eBike tour stands out. For those seeking a deep dive into Tuscany’s flavors and landscapes, the Val di Chiana wine tour delivers. And if privacy and personalized service are your priority, the Cortona private eBike is the way to go.
No matter which tour you choose, booking ahead will ensure you secure your spot in these popular experiences. Now, all that’s left is to get your pedals turning and enjoy the best of Arezzo on two wheels.
