Cortona is a magical place to explore, thanks to its beautiful views, rich artistic heritage, and authentic Tuscan charm. While wandering its winding streets, you’ll find that the town offers more than just pretty scenery—it’s a hub for unique experiences. Among our favorites are a heartfelt journey through local history, a luxurious visit to a historic winery, and a relaxing organic wine tasting in the countryside. Each of these gives you a different way to connect with Cortona’s soul, whether through history, wine, or scenery.
One experience we particularly love is Cortona: Journey Through Time. It’s not just about seeing sights; it’s about feeling the heartbeat of the place with guides who truly know their history and culture. For wine lovers, the Tenimenti d’Alessandro tour offers a taste of Tuscany’s finest, set in a stunning estate. And for those who want a fun, relaxed outing, the Organic wines tasting at Colle Acacia’s vineyards provides a delicious way to soak in the landscape while sampling excellent local wines.
Below, you’ll find detailed descriptions of each experience, helping you decide which suits your interests, schedule, and budget best.
1. Cortona: Journey Through Time
This tour offers a deep dive into Cortona’s art, history, and traditions. It’s a full-day experience that goes beyond just sightseeing. Instead, you’ll walk through the town’s most meaningful sites, guided by locals who have a personal connection to the area. What makes this tour stand out is its focus on immersion — it’s not about rushing past monuments but about feeling the history and soul of Cortona. The tour includes visits to more than 60 fully functional tractors, which add an authentic rural touch if you’re interested in the agricultural side of Tuscany’s past.
The guides are experts with ties to the community, sharing stories and insights that you won’t find in guidebooks. The tour is ideal for travelers who want to understand Cortona’s cultural fabric and walk through history with a passionate local. The experience may include walking through narrow alleyways, visiting historical sites, and enjoying local traditions that have persisted over centuries.
A key highlight is the balance between seeing beautiful sights and engaging directly with the local culture. Since it’s a full-day outing, be prepared for some walking, but it’s well worth the effort for the authentic perspective you gain. The reviews consistently rate this experience a perfect 5/5, praising its depth and engaging storytelling.
Bottom line: This tour is perfect for history and culture enthusiasts who want a comprehensive, personal experience of Cortona’s past and present.
2. Tenimenti d’Alessandro – Visit the winery and wine tasting
For those who love wine and want to enjoy a luxurious experience in Tuscany, Tenimenti d’Alessandro is a standout choice. This historic winery is situated in an exclusive location on the hills of Tuscany, offering sweeping views and a peaceful setting. The visit includes a tour of the estate, where you’ll learn about their own local production, including the secrets behind their classic Tuscan wines.
The estate is a private, refined place—an ideal spot to appreciate the craftsmanship that goes into every bottle. The experience often includes tasting sessions where you sample a variety of wines, giving you a real taste of Tuscany’s wine-making traditions. The guides are knowledgeable and passionate, sharing insights into the process from grape to glass.
Guests often comment on the serene atmosphere and the high quality of the wines, which are carefully crafted on-site. The experience is perfect for couples, wine aficionados, or anyone looking to combine leisure with cultural appreciation. Since the tour can be tailored, it’s suitable for a range of schedules—just check availability to see the best times.
Bottom line: If you’re after a refined, educational wine experience in a historic setting, this tour offers excellent value for wine lovers seeking a quiet, quality-focused outing.
3. Cortona: Organic wines tasting at Colle Acacia’s vineyards
For a relaxed, scenic experience, the organic wine tasting at Colle Acacia is a great choice. This four-hour tour combines beautiful vineyard walks with tasting some of the best organic wines produced locally. At just $59 per person, it offers excellent value, especially considering the quality of wines and the setting.
You’ll sample four different wines, including a Super Tuscan blend, a Syrah, and a rosé, paired with local delicacies like pecorino cheese and ham. The tasting is held amid the rolling hills of Colle Acacia’s vineyards, giving you plenty of opportunity to soak in the landscape. The guides are friendly and eager to share their knowledge about the vines and organic farming practices.
During the walk through the vineyard, you’ll learn about the different grape varieties and how the terroir influences the flavors. It’s a perfect experience for those who want to enjoy a laid-back, delicious afternoon in Tuscany, especially if you appreciate organic wines and scenic views. The only potential downside is that the tour is relatively short, but the quality of the wines and setting more than make up for it.
Bottom line: This tasting is ideal for wine lovers seeking a peaceful, scenic experience with a focus on organic and local products.
How to Choose
Choosing the right Cortona experience depends on your interests, schedule, and what kind of memories you want to bring home. If you’re passionate about history and culture, the Journey Through Time offers an immersive and personal look at the town’s soul. For wine aficionados craving a luxurious visit, the Tenimenti d’Alessandro tour combines education with elegance. If you prefer a light, scenic, and casual outing, the organic wine tasting at Colle Acacia provides a relaxed way to enjoy Tuscany’s landscape and wines.
Consider your budget, how much time you have, and whether you prefer culture or wine tasting. Book early, especially in high season, to secure your preferred time slot. Check availability ahead of time to ensure a smooth experience.
Final Thoughts
Cortona offers a rich set of options for travelers eager to explore beyond the surface. If you want to truly connect with its history and traditions, the Journey Through Time is a highly recommended choice. Wine lovers seeking a peaceful yet educational outing will find the Tenimenti d’Alessandro tour perfect. And if a casual, scenic tasting is more your style, the organic wines at Colle Acacia deliver a delightful afternoon.
Each offers a different way to experience Cortona’s natural beauty and rich culture. No matter your preference, booking early guarantees a memorable experience. These tours are small enough to feel personal but packed with authentic, meaningful moments—just what you need to make the most of your time in Tuscany.