Cortona is a charming hill town in Tuscany that offers more than just beautiful views and cobblestone streets. It’s a place where you can truly dive into local flavors, crafts, and history. Whether you’re a wine lover eager to taste limited-production bottles or a history buff wanting to walk through ancient streets, Cortona has tours tailored for every interest. We especially like the Journey Through Time for its engaging mix of art, history, and local life—it’s perfect for those who want an authentic cultural experience. And if wine tasting is your priority, the small-group Buccelletti wine tours offer a genuine taste of Tuscany’s boutique wineries.
Cortona’s tours stand out because they combine the region’s rich flavors with its deep history. Many of the experiences are led by local families or experts, offering a personal touch that large group tours often lack. As you explore, you’ll find options suited for all budgets, schedules, and interests, from leisurely tastings to in-depth cultural walks.
Quick Overview of the Best Tours in Cortona
Our list includes a variety of experiences to match diverse interests. You’ll find wine tasting tours that focus on limited-production, boutique wines, such as the Castiglion Fiorentino: Tour, Tasting & Charcuterie Board, and more casual tastings like the Buccelletti Wine Flight. For those wanting a deeper culture, the Journey Through Time offers a guided exploration of art, history, and local traditions. If you prefer scenic walks paired with wine, Colle Acacia’s organic vineyard tasting combines beautiful vistas with delicious wines. And for a full-day adventure, the Tenimenti d’Alessandro provides an in-depth look at a historic winery in Tuscany.
Below, we explore each of these options in detail so you can find the perfect tour for your trip.
1. Castiglion Fiorentino: Tour, Tasting & Charcuterie Board
At number 1 on our list, this tour offers an immersive visit to a family-run winery in the lush Valley of Chio. You’ll explore the property, including the historic family chapel dating back to 1625, the olive mill, and the vineyards. The highlight is a tasting of three wines, carefully paired with local cheeses, salumi, focaccia, and their own olive oil.
What makes this experience stand out is its intimate atmosphere and the fact that the winery is directed solely by women. Their wines are limited, not mass-produced, so you’re tasting unique products from a winery with 400 years of history. The guided tour (about 20 minutes) helps you connect with the land and the process, while the hour-long tasting allows ample time to savor the flavors. The setting in the rolling hills of Tuscany makes every sip feel authentic.
Guests rave about the personalized service and quality of wines, with one calling it “Really enjoyed it.” This tour is perfect if you’re interested in learning about traditional winemaking and tasting wines that aren’t available everywhere.
Bottom line: Ideal for wine lovers who want an authentic, small-scale experience with a rich history.
2. Castiglion Fiorentino: Buccelletti Wine Flight
For a more casual, no-fuss wine tasting, the Buccelletti Wine Flight offers an hour of tasting three different wines paired with fresh bread and their own Extra Virgin Olive Oil. This tour is especially suited for those who want a quick yet informative experience without committing to a full tour. The winery is again a boutique, family-run operation, and the wines are limited-production, making every sip special.
The tasting is led by a friendly guide who explains each wine’s character and the family’s approach to winemaking. One review highlights the “Very friendly lady who explained everything well,” reflecting the welcoming atmosphere. The setting in the beautiful Valley of Chio provides a peaceful backdrop for savoring these wines.
Priced at just $25 per person, this experience offers great value for a relaxed afternoon. It’s particularly good for travelers short on time or those wanting a straightforward wine experience that still captures the essence of Tuscany’s boutique wine scene.
Bottom line: Perfect for a quick, friendly introduction to local wines without fuss.
3. Castiglion Fiorentino: Buccelletti Wine Tour & Tasting
This tour combines a guided visit of the property with a tasting of three wines, plus a plate of fresh bread and their delicious Extra Virgin Olive Oil. Starting from Via Santa Cristina, the tour lasts about 1.5 hours, making it manageable for most travelers. The visit explores the family chapel, olive mill, and vineyards, giving you a well-rounded look at the estate’s heritage.
What makes this tour stand out is the focus on both wine and the land—your guide shares insights about the history, the family’s 400-year tradition, and the local landscape. The wines are limited in production, ensuring you’re tasting something authentic and crafted with care. Guests consistently praise the experience with reviews like “Really enjoyed it,” echoing the memorable nature of the visit.
This tour suits those who want a detailed introduction to a historic winery and enjoy pairing wine tastings with regional foods. The value is high given the depth of experience and quality of wines offered.
Bottom line: Best for travelers who want a comprehensive look at a historic, family-run winery with a focus on authenticity.
$39.86 per person
4. Cortona: Journey Through Time
If history and culture are your main interests, the Journey Through Time offers an engaging exploration of Cortona’s art, history, and traditions. This full-day experience (check availability for departure times) takes you beyond the usual tourist spots and deep into the local life of this ancient town.
Guided by local experts with a strong connection to the area, you’ll walk between the past and the present, discovering art, architecture, and stories that have shaped Cortona. The tour is not just about viewing monuments but about enjoying the memory and soul of the place. The tour includes visits to historic sites, local workshops, and hidden corners that reveal the true character of Cortona.
This experience is perfect for travelers interested in authentic cultural encounters and for those who want a well-rounded understanding of the town’s significance. The tour’s focus on local stories makes it memorable.
Bottom line: Ideal for history and art enthusiasts seeking an in-depth, guided cultural experience.
5. Cortona: Organic wines tasting at Colle Acacia’s vineyards
For those who want to combine scenic beauty with wine tasting, the Organic Wines Tasting at Colle Acacia offers a four-hour visit to a scenic vineyard near Cortona. You’ll enjoy tasting four wines, including Cortona Syrah, a Super Tuscan blend, and a Rosé, all paired with local delicacies like pecorino cheese and ham.
The highlight here is the chance to walk through the vineyard, learning about the vines and sustainable farming practices. The serene surroundings make it a relaxing experience, perfect for those who want to escape the hustle and enjoy the landscape at a leisurely pace. The landscape views are especially striking, adding to the overall experience.
The single review praises the experience, highlighting the friendly staff and the high-quality wines. This tour offers good value if you’re interested in organic winemaking and Tuscany’s countryside.
Bottom line: Great for wine lovers who want a combination of beautiful scenery, organic wines, and local food.
$59 per person
6. Tenimenti d’Alessandro – Visit the winery and wine tasting
Rounding out our list, this full-day experience visits Tenimenti d’Alessandro, an historic winery in Tuscany’s hills. Here, you’ll tour the ancient Villa-Farm and enjoy a private tasting of their own wines, produced on-site. The exclusive atmosphere and historic setting make this a special outing for wine connoisseurs and lovers of craftsmanship.
The winery’s own local production means you’re tasting wines made with care in a historic setting. The experience is ideal for travelers seeking a more luxurious, in-depth exploration of Tuscany’s wine culture. The staff’s knowledge and the historic ambiance add to the overall value.
While details about the price aren’t specified, this tour is perfect for those who want a premium, comprehensive experience and are willing to splurge a bit for exclusivity.
Bottom line: Well suited for serious wine enthusiasts interested in historic estates and private tastings.
How to Choose Your Perfect Tour in Cortona
When picking a tour, consider your priorities: budget, time, interests, and physical activity level. If you’re short on time and want a quick taste of local wines, the Buccelletti Wine Flight offers great value. For a deep dive into the history and art of Cortona, the Journey Through Time is ideal. Wine lovers with a passion for authentic, small-scale producers should opt for the Castiglion Fiorentino or Buccelletti experiences.
Those interested in organic wines or scenic landscapes should consider the Colle Acacia vineyard. And if you’re looking for a premium experience, Tenimenti d’Alessandro offers an exclusive look at Tuscany’s historic wine estates.
Booking early is wise, especially in peak season, to secure your preferred time and avoid disappointment.
Final Thoughts
Cortona’s variety of tours ensures there’s something for all — from quick tastings to immersive cultural walks. If you’re a wine enthusiast, the boutique, family-run wineries provide authentic tastes you can’t find elsewhere. History buffs and art lovers should not miss the guided Journey Through Time for its engaging narrative. Both options give a real flavor of what makes Cortona special.
Whether your trip is focused on wine, history, or local culture, planning ahead and booking early will help you make the most of your time here. Cortona’s tours are a perfect way to deepen your experience of this enchanting Tuscan town.