Arezzo, in the heart of Tuscany, is perfect for cycling tours. Its gentle rolling hills, historic towns, and stunning countryside make for memorable rides, especially with the help of eBikes. Whether you’re after a relaxed sightseeing experience or a full-day adventure, Arezzo offers options for all levels. We particularly love the Cortona eBike tours for their mix of beautiful vistas and cultural stops, such as Villa Bramasole from Under the Tuscan Sun or the panoramic Fortezza di Girifalco. Plus, the combination of history, nature, and the ease of electric bikes makes exploring Tuscany’s landscapes both fun and accessible.
For those wanting a broader experience, some tours include wine tastings, while others focus on medieval charm or full immersion in Val d’Orcia. All these options give you a chance to see Tuscany in a way that’s active but not exhausting, with plenty of opportunities to stop and soak in the scenery or enjoy a local delicacy.
1. Cortona – Easy guided eBike tour around the Etruscan City
At number 1, this popular guided eBike tour in Cortona offers an easy way to explore a charming hilltop city famed for its Etruscan roots. This 2 to 3-hour shared tour is limited to just 2-3 people, ensuring a relaxed experience. The route takes you along paved streets and historic paths, stopping at key sites like Fortezza di Girifalco, Basilica di Santa Margherita, and Eremo Le Celle, the peaceful sanctuary of Franciscan monks.
What makes this tour stand out are the beautiful vistas and the informative guides who bring Cortona’s stories to life. You’ll ride on quality eBikes, which are ideal for those who want a gentle ride without sacrificing the scenery. The stops include a scenic viewpoint below Girifalco fortress, inside the Basilica, and at Villa Bramasole — the house made famous by Under the Tuscan Sun. With consistent praise for the guide’s friendliness and the bikes’ quality, this tour is perfect for anyone looking for a low-impact, high-scenery outing.
Bottom Line: An excellent choice for those wanting a relaxed introduction to Cortona’s sights and history, combining light cycling with enriching stops.
2. Cortona – eBike tour and wine tasting in the Val di Chiana
![Cortona - eBike tour and wine tasting in the Val di Chiana [+40]](https://happytovisit.com/wp-content/uploads/2025/10/cortona-ebike-tour-and-wine-tasting-in-the-val-di-chiana-40.jpg)
For around $188, the eBike and wine tasting tour in Val di Chiana is a full-day experience that combines scenic cycling with a taste of Tuscany’s renowned wines. Starting 20 minutes by car from Cortona, this tour covers about 5 to 6 hours, making it ideal for those with a full day to spare.
The ride winds through the rolling hills of the Val di Chiana, with stops at vineyards and olive groves. You’ll enjoy a leisurely cruise along the iconic white roads, passing cypress-lined hills and vineyards that seem to stretch forever. The highlight? The wine tastings and a delicious lunch, which guests say are “out of this world.” The guide shares stories about the local wine production, adding depth to the experience. The bikes are brand new, and the scenery — especially at sunset — is spectacular.
This tour suits travelers who want a mix of physical activity, cultural education, and culinary indulgence. It’s particularly praised for the friendliness of the guides and the quality of the wine. Keep in mind that the group size is limited for comfort, and some previous guests mention it’s a “wonderful, easy ride through the hills.”
Bottom Line: Perfect for wine lovers and those seeking a full-day, immersive Tuscany experience with scenic cycling and gourmet treats.
3. Castiglion Fiorentino – eBike tour in the Tuscan countryside
Coming in at number 3, the Castiglion Fiorentino eBike tour offers a 3.5-hour ride through Tuscany’s lush landscape, with a special focus on Montecchio Castle. This tour, priced at about $159 per person, is praised for its ease and the quality of the bikes.
The route takes you away from crowded tourist spots, giving you time to enjoy the serenity of the green hills and natural scenery. The highlight is the visit to Montecchio Castle, a 1,000-year-old fortress that offers views of the surrounding countryside. The guide is commended for being helpful and knowledgeable, making the experience accessible for all levels, including those new to eBiking.
Guests often mention how the electric bikes make the ride manageable, even on slightly challenging terrain. The landscape’s authenticity is a key selling point, with ample photo opportunities along the way. This tour is best suited for travelers who want a comfortable ride with a touch of history and nature. It’s also a good pick for those who prefer less crowded routes.
Bottom Line: An excellent option for history enthusiasts and nature lovers seeking a moderate, scenic ride with a historical highlight.
4. Pienza – Ebike tour for a full immersion in Val d’Orcia
This full immersion eBike tour in Val d’Orcia offers a 3.5-hour journey through one of Tuscany’s most iconic landscapes. Starting from Pienza, a Renaissance town and UNESCO World Heritage site, the tour covers the breathtaking vistas of rolling hills, cypress-lined roads, and fields of lavender and wheat.
Led by a professional guide, you’ll experience the natural beauty and artistic charm of the region. The guide, Roberto, is praised for making the tour both fun and educational, sharing insights about the landscape and local culture. The route includes stops at small towns, natural springs, and Roman baths, adding variety and interest. The bikes are comfortable and well-maintained, suitable for all levels.
Guests note that this tour is ideal for those wanting to see Tuscany’s countryside in a relaxed way, with plenty of photo stops and cultural insights. The value for money is high, considering the included stops and the quality of the guide.
Bottom Line: Best for travelers seeking a scenic, cultural, and leisurely ride through Tuscany’s classic landscapes.
5. CORTONA Medieval Charme: PRIVAT E-bike Experience, Top Quality!
Number 5 is a private eBike tour in Cortona that offers a tailored experience. The Medieval Charme tour lasts 3 to 4 hours and costs around $311 per person, making it the most premium option on our list.
This tour visits top landmarks like Villa Bramasole, Santa Margherita Basilica, and Fortezza di Girifalco, with a focus on personalized storytelling. The route begins at a panoramic viewpoint over Valdichiana, then takes you to the famous Villa Bramasole, the scene of Under the Tuscan Sun. The guide is highly praised for their knowledge of local history and the personalized service. The trip also includes stops at the Santa Margherita church and the fortress, offering both spiritual and historic sights.
Guests who choose this private option appreciate the flexibility and depth of the experience, especially if they’re interested in cultural stories, photography, or simply enjoying a more exclusive ride. Because of the cost, it’s best suited for travelers seeking a more premium, tailored experience rather than a group tour.
Bottom Line: Ideal for those who want a private, in-depth exploration with a higher level of comfort and customization.
6. Bike Ride immersion Val d’Orcia
Number 6 on our list is the Bike Ride in Val d’Orcia, offering a 3 to 6-hour ride through some of Tuscany’s most photographed scenery. Priced at about $138.91 per person, it’s an affordable way to experience the region’s natural beauty.
The tour covers approximately 20 miles (32 km) of rolling hills, with an option for eBikes if needed. The route begins in Pienza, crossing lush pastures and cheese factories producing Pecorino. It then descends to Bagno Vignoni, a thermal spa town with ancient stone buildings around warm springs. Riders can choose to return by bike or via van, depending on their energy level.
Past participants highlight how Panos, the guide, customizes the experience and hits all the right spots, including picnics and scenic viewpoints. The ride is suited for travelers with a moderate fitness level who want an authentic, less commercialized look at Tuscany’s countryside.
Bottom Line: A good-value, scenic ride for those wanting a longer, relaxed exploration of Val d’Orcia’s classic vistas.
7. Half Day Tour by Ebike Around Cortona
Finally, the Half Day eBike Tour provides a quick but thorough taste of Cortona’s highlights in about 2 to 4 hours. For around $174, you’ll visit Villa Bramasole, Fortezza del Girifalco, and the Basilica of Santa Margherita.
The route starts at the scenic Parterre di Cortona, with stops at the fortress built by Cosimo de Medici, and the spiritual Basilica. The guide shares fascinating stories about each site, including the famous film house, Villa Bramasole. The ride is accessible for most, with a focus on cultural and scenic highlights within a manageable timeframe.
Reviews praise the guide’s storytelling ability and the quality of the bikes. This tour is best suited for those with limited time but still wanting a comprehensive taste of Cortona’s sights.
Bottom Line: A compact, engaging option for travelers seeking a quick yet meaningful ride through Cortona.
How to Choose the Best Bike Tour in Arezzo
When selecting your perfect bike adventure, consider your fitness level, time availability, and interests. For a relaxed overview of Cortona’s key sites, the Easy guided eBike tour is ideal. If you’re passionate about wine and want a full-day experience, the Wine tasting tour offers excellent value.
For those interested in history and culture, the private Medieval Charme provides an in-depth, personalized journey. Budget travelers and those craving a longer ride may prefer the Val d’Orcia or full immersion in Pienza, both of which combine scenic views with cultural stops.
Booking early is wise, especially during peak season, to ensure availability and secure your preferred time slot. Consider also your comfort with cycling; eBikes make even challenging terrain manageable, so don’t let fitness hold you back.
Final Thoughts
Arezzo’s cycling options run the gamut from scenic tours around historic towns to full-day explorations of Tuscany’s iconic landscapes. For a relaxed introduction, the Cortona guided eBike is hard to beat, offering great value and memorable stops. Those seeking a more luxurious or private experience will find the Medieval Charme tour perfect, while wine lovers can indulge in the wine tasting and countryside ride.
Whether you’re on a tight schedule or looking to spend a day immersed in Tuscany’s beauty, these tours offer something for every cyclist. Booking early, especially in high season, guarantees you a spot on one of these fantastic rides. Now, all that’s left is to pick your adventure and pedal into the Tuscan sunset.