When exploring the ancient hill town of Cortona, several excellent tours stand out. The practical Half-Day E-Bike Tour lets you comfortably cover more ground while enjoying panoramic Tuscan views. I’m especially fond of the Buccelletti Wine Tour – this family operation gives visitors an authentic peek into Tuscan winemaking, complete with an on-site olive mill. The Private Walking Tour brings Cortona’s Etruscan history to life through its medieval streets and ancient walls. For those wanting to combine scenery with local flavors, the Val Di Chiana E-Bike Tour offers a perfect mix: countryside cycling plus stops at a working farm and winery.
Let’s look at my favorite Cortona tours in detail.
Key Points
- The Half-Day E-Bike Tour is a 3-hour guided experience through the Tuscan countryside, visiting Villa Bramasole, Fortress of Girifalco, and Basilica of Saint Margaret.
- The Buccelletti Wine Tour & Tasting offers a 1.5-hour winery visit with three wine tastings, bread, and olive oil, along with optional charcuterie and olive oil education.
- The Private Walking Tour of Cortona is a 3-hour exploration of the town’s Etruscan history, historical core, and scenic views, with flexible booking options and family-friendly itinerary.
- The Private 2-Hour Guided Tour covers major historical sites in Cortona, such as Piazza della Repubblica and Palazzo Comunale, with knowledgeable English and Italian-speaking guides.
- The Val Di Chiana E-Bike Tour is a 5-hour eco-friendly experience through the Tuscan countryside, including a local farm and winery visit, suitable for most participants.
Half Day E-Bike Tour to Highlights Around Cortona
Though the picturesque town of Cortona offers a wealth of historic attractions, visitors can explore the best sights on a convenient half-day e-bike tour. Priced from $194.66 per person, this 3-hour guided experience takes adventurers through the Tuscan countryside, visiting highlights like Villa Bramasole from the movie “Under the Tuscan Sun” and the stunning Fortress of Girifalco.
Along the way, the tour also stops at the Basilica of Saint Margaret of Cortona and the optional Hermitage Le Celle, offering a chance to learn about local products and culture. Riders will enjoy the unique experience of exploring ancient towns and historical paths on hybrid e-bikes, away from traffic.
The tour includes e-bikes, helmets, insurance, an authorized guide, a typical Tuscan lunch, and private transfers, making it a hassle-free way to discover Cortona’s top attractions. With free cancellation up to 24 hours in advance, this tour is an excellent choice for those seeking an immersive and active way to experience the beauty of Tuscany.
Read our full review: Half Day E-Bike Tour to Highlights Around Cortona Review
Book now: Check availability
Castiglion Fiorentino: Buccelletti Wine Tour & Tasting
Situated in the picturesque Valley of Chio, the Buccelletti Winery offers visitors an immersive journey through the rich winemaking history of Castiglion Fiorentino. This family-run boutique winery, directed exclusively by women, has been producing exquisite wines since 1625, inviting guests to taste their limited-production offerings.
The 1.5-hour guided tour includes a visit to the family chapel, vineyards, cellar, and historic olive mill, culminating in a tasting of three wines accompanied by fresh bread and extra virgin olive oil. Guests can also opt to add a charcuterie board or an educational olive oil tasting to their experience.
Beyond the wine tasting, the winery provides ample opportunities for relaxation, with garden seating and outdoor games like bocce ball.
For those seeking a more comprehensive experience, the tour, tasting, and lunch option is available with a 24-hour reservation.
Whether exploring the winery’s rich heritage or indulging in the authentic Tuscan countryside, the Buccelletti Wine Tour offers an unforgettable culture.
Read our full review: Castiglion Fiorentino: Buccelletti Wine Tour & Tasting Review
Book now: Check availability
Cortona: 3-Hour Private Walking Tour
Explore the charming town of Cortona on a 3-hour private walking tour, delving into its rich Etruscan history and captivating landscapes.
This flexible tour allows you to reserve now and pay later, with no upfront payment required. And if your plans change, you can cancel up to 24 hours in advance for a full refund.
During the tour, you’ll discover Cortona’s historical core, including the cathedral, medieval old town, and splendid panoramas.
Your knowledgeable guide will bring the town’s artistic and historical significance to life, while you admire the fabulous scenery and learn about the Etruscan roots.
Suitable for families, the itinerary isn’t particularly demanding.
With an overall rating of 4.9/5 based on 9 reviews, this tour has received high praise from various traveler types.
Enjoy the charm of Cortona and embark on an unforgettable journey through its past and present for $156.15 per person.
Read our full review: Cortona: 3-Hour Private Walking Tour Review
Book now: Check availability
Cortona: Private 2-hour Guided Tour
This private 2-hour guided tour of Cortona offers a comprehensive introduction to the town’s rich history and architectural highlights. Priced at $249.84 for up to 20 participants, the tour takes visitors through the Piazza della Repubblica, Palazzo del Capitano del Popolo, Palazzo Comunale, Palazzo Casali, and the town cathedral, providing insights into the city’s Roman, medieval, and Neoclassical heritage.
Led by knowledgeable English and Italian-speaking guides, the tour allows visitors to explore the historical sites at a leisurely pace.
With a 5/5 overall rating based on 13 reviews, the tour is praised for its informative and engaging presentations, as well as the guides’ accommodating nature.
Booking is flexible, with the option to reserve now and pay later, and free cancellation up to 24 hours in advance. However, the tour isn’t suitable for wheelchair users. Comfortable shoes are recommended, and tour availability should be checked when booking.
Read our full review: Cortona: Private 2-hour Guided Tour Review
Book now: Check availability
Cortona: Guided E-Bike Tour of Tuscanys Hidden Gem
Exploring Cortona’s stunning countryside has never been easier than with the guided e-bike tour. At £121.71 per person, this 3-hour, 12-14 km ride takes visitors through the hidden gems of Tuscany, including the Hermitage Le Celle, Basilica of Saint Margaret of Cortona, Fortress of Girifalco, and Villa Bramasole.
The tour’s eco-friendly e-bikes provide powerful assistance, allowing participants to enjoy the scenic routes without physical strain. With a maximum group size of 2-3 bookings, the experience ensures comfort and personalized attention from the expert guide, who shares insights into local history and culture.
Cancellation is free up to 24 hours in advance, and a reservation with pay later option is available. However, the tour may not be suitable for individuals with mobility impairments or over 264 lbs (120 kg).
Participants should wear appropriate sportswear and avoid sandals, flip flops, or loose clothing.
Read our full review: Cortona: Guided E-Bike Tour of Tuscanys Hidden Gem Review
Book now: Check availability
Cortona: Guided Walking Tour
Setting out on a guided walking tour of Cortona provides visitors an immersive way to uncover the historic town’s Etruscan origins and Renaissance charm. Priced from $166.56 per person, the 2-hour tour takes guests through the town’s main piazzas, including Piazza della Repubblica, Piazza Luca Signorelli, and Piazza del Duomo.
Along the way, knowledgeable guides fluent in multiple languages share insights into Cortona’s storied past and architectural highlights, such as the Palace of the Captain of the People and the Girifalco Fortress.
With the flexibility of free cancellation up to 24 hours in advance and the option to reserve now and pay later, this walking tour offers a convenient and enriching way to explore the essence of Cortona.
Based on 5-star reviews, the tour’s standout features include the guide’s expertise, enthusiasm, and ability to provide a thorough, informative experience that brings the town’s Etruscan and Renaissance legacy to life.
Read our full review: Cortona: Guided Walking Tour Review
Book now: Check availability
Cortona: Val Di Chiana E-Bike Tour With Optional Wine Lunch
Venture beyond Cortona’s historic center and explore the picturesque Val di Chiana region on an exhilarating e-bike tour. Priced from €164 per person, this 5-hour adventure lets you discover the Tuscan countryside on eco-friendly electric bikes.
Expert guides lead the way, sharing insights into the area’s rich history and culture as you pedal through peaceful gravel roads away from traffic.
Highlights include admiring vibrant wildflowers, wheat crops, and vineyards, as well as visiting a local farm and winery for an optional wine tasting and light lunch.
The tour is suitable for most participants, but pregnant women, those with mobility issues, and individuals over 264 lbs are advised to avoid it.
Remember to bring appropriate sportswear and avoid loose clothing or sandals.
With a 5-star rating based on 8 reviews, this tour offers a fantastic way to experience the natural beauty of the Val di Chiana region.
Read our full review: Cortona: Val Di Chiana E-Bike Tour With Optional Wine Lunch Review
Book now: Check availability
Sum Up
Cortona offers a variety of tours that allow visitors to explore the city’s historic sites and surrounding Tuscan countryside. From guided walking tours to e-bike adventures, there’s something for all. Whether you’re interested in wine tastings, architectural landmarks, or scenic vistas, Cortona’s tour options provide an immersive way to experience the charming Italian town and its picturesque region.