Arezzo is not just about stunning landscapes and medieval streets; it’s a lively hub for authentic tours and experiences that reveal Tuscany’s rich culture, flavors, and history. Whether you’re a wine enthusiast eager to taste world-class Brunello or a history buff wanting to walk through ancient Etruscan walls, Arezzo offers something special. We particularly love the Tour through the vineyards and wine and olive oil tasting in Tuscany for its intimate setting and storytelling, and the Brunello Wine Tour and Val D’Orcia Landscape for combining scenic beauty with exceptional wine tasting. These experiences stand out for their local focus and expert guides, making Tuscany’s charm accessible and memorable.
Arezzo’s tours span from tasting sessions in historic wineries to guided walking explorations of its ancient streets, giving visitors a well-rounded experience of Tuscany’s diverse offerings. For those wanting to learn cooking, the Cooking class in a Tuscan Villa near Cortona combines culinary skill-building with relaxed farm-to-table flavors. With a variety of options suited for different budgets, interests, and time frames, you’re sure to find something that fits your travel style.
1. Tour through the vineyards and wine and olive oil tasting in Tuscany
At number 1 on our list, this 1.5-hour experience immerses you in the heart of a Tuscan vineyard close to Arezzo. Hosted on a farm near a Renaissance villa of 1558, the tour combines art, history, and wine. Virginia, the guide, brings stories of the estate’s origins while you sample wines, cheeses, and prosciutto. Guests love her engaging storytelling—”We learned a lot and enjoyed every minute,” said one reviewer. The highlight is tasting fresh Shiraz grapes and hearing about the vineyard’s journey through history.
What makes this tour special is its intimate atmosphere and focus on art and tradition, perfect for those with a curiosity for Tuscany’s cultural landscape. The scenery alone makes it worthwhile, but the real prize is the tasting experience and the chance to learn about Tuscan wine-making in a relaxed setting. It’s a budget-friendly option that provides a deep dive into regional flavors. If you’re after a brief yet rich introduction to Tuscany’s viticulture and olive oil heritage, this tour is a top pick.
Bottom Line: An excellent choice for wine lovers, art enthusiasts, and anyone seeking a taste of authentic Tuscan life without breaking the bank.
2. Brunello Wine Tour and Val D’Orcia Landscape
For around $255, this half-day private tour promises a memorable experience exploring Tuscany’s most revered wines and scenic countryside. The tour begins with a customizable visit to a family-owned winery near Montalcino, where you’ll taste the world-famous Brunello di Montalcino—a 100% Sangiovese wine considered one of Italy’s finest. The guide, Fabrizio, who is a sommelier, shares insights into the wine’s production and the estate’s history, making each tasting both educational and enjoyable.
Beyond the winery, the tour takes you through the stunning Val d’Orcia, a UNESCO World Heritage site filled with medieval hill towns and ancient monasteries. Guests consistently describe Fabrizio as very knowledgeable and attentive, with one noting, “He customized the day based on our preferences and showed us things we’d never find on our own.” The combination of wine, landscape, and history makes this tour ideal for anyone wanting a comprehensive Tuscan experience.
Bottom Line: Best suited for wine connoisseurs who also want to see Tuscany’s iconic scenery, with a personal touch from a local expert.
3. Walking Tour in Cortona
At number 3, this 1.5 to 2-hour guided walk takes you through the picturesque streets of Cortona, a town made famous by Under the Tuscan Sun. Starting from Piazza Garibaldi, your guide leads you past the main street, key churches, and hidden Etruscan walls. The tour includes visits to the Chiesa San Francesco, with its relics, and the Duomo di Cortona, where you can compare Italian church architecture and art.
This tour is especially appreciated for its personalized attention—one reviewer mentioned how guide Elisona’s understanding of local history made the experience more meaningful. The walk offers a great introduction to Cortona’s 3000-year-old history, combining architecture, art, and local stories in one accessible package. It’s perfect for travelers with limited time but wanting a deep culture.
Bottom Line: A highly recommended way to get to know Cortona’s main sights in a relaxed, friendly atmosphere, ideal for history lovers.
4. Cooking class in Tuscan Villa near Cortona
Number 4 on our list is a 5-hour hands-on cooking class that turns you into a Tuscan chef. You’ll be welcomed by the host chef in his home, where the atmosphere is as warm as the food you’ll prepare. The class covers making fresh pasta, ragu, and tiramisu, all with ingredients produced on-site, including their natural olive oil. During breaks, you’ll taste their extra virgin olive oil and sip local wine—creating a true Tuscan feast.
Guests rave about the friendliness of the family and the slow-paced, detailed instruction. One reviewer called the experience “delightful, educational, and delicious,” emphasizing the chance to make dishes from scratch. After cooking, everyone sits down together to enjoy the meal, which makes it more than just a class—it’s a taste of Tuscan family life. It’s ideal for foodies, couples, or small groups who want a personalized, authentic experience.
Bottom Line: A memorable, hands-on cooking experience perfect for those who want to learn Tuscan culinary secrets in a friendly family setting.
5. Arezzo Experience: Winery Tour and Wine Tasting
At number 5, this short but sweet winery visit offers an intimate tasting of three wines paired with cured meats from Azienda Villani. The tour includes a guided estate tour and an olive oil tasting with bruschetta, making it a well-rounded experience. The winery is located just outside Arezzo, making it convenient and focused on local traditions.
Guests appreciate Claudia, the host, for her warm hospitality and her deep knowledge of wine production. One reviewer said, “We had a very pleasant couple of hours tasting regional wines and learning about their history.” This experience is ideal for travelers seeking a quick, authentic tasting with a focus on local flavors.
Bottom Line: Great for those who want a brief, personal introduction to Tuscan wine and olive oil without a full-day commitment.
6. 2 hours Arezzo group walking tour
Number 6 offers a 2-hour walking tour of Arezzo, perfect for a quick overview of the city’s main sights. Led by a friendly and knowledgeable guide, this tour covers the city’s architectural highlights and art masterpieces, including the Cathedral with its stained glass and paintings.
While reviews note that the tour could include more monuments like San Domenico, the guide’s personable style keeps it engaging. One comments, “It’s a good way to get a feel for the city in a short time,” making it suitable for travelers on a tight schedule. It’s a good introductory tour that balances sightseeing with storytelling.
Bottom Line: Ideal for a short, informative overview of Arezzo’s key sites, especially if you’re only in town briefly.
7. Educational Olive Oil Tasting
Number 7 is an hour-long private visit to a historic family-run farm in Val di Chio. The tour focuses on the art of olive oil production, with tastings paired with Tuscan bread. Visitors learn about traditional methods dating back to 1625, making it both educational and flavorful.
The setting is beautiful, and the owners are praised for being friendly and informative. One reviewer said, “The family’s story and their olive oil are unforgettable,” emphasizing the personal touch. This tour suits foodies, olive oil lovers, or anyone interested in Tuscany’s agricultural traditions.
Bottom Line: A perfect quick, authentic experience for those wanting to understand and taste real Tuscan olive oil.
8. All Tuscany Wine Tour
Number 8 combines tastings from three major Tuscan wine regions—Brunello di Montalcino, Chianti Classico, and Bolgheri. Hosted in a unique location beside a Renaissance villa, it offers a chance to compare Supertuscans with classic wines. The small business behind the tour guarantees quality and attention.
This experience is suited for wine lovers wanting to broaden their tasting horizons and appreciate Tuscany’s diverse wine landscape in one sitting. Guests appreciate the focus on wine from different areas and the exclusive setting. The tour lasts about 2 hours, making it a manageable, rich taste of Tuscany’s wine excellence.
Bottom Line: Perfect for those who want an all-in-one overview of Tuscany’s wine regions in a short, quality-focused session.
9. Tenute di Fraternita – Wine tasting in the Arezzo countryside
At number 9, this 1.5-hour wine tasting takes place at a traditional farmhouse, emphasizing authenticity and organic practices. You’ll sample wines while enjoying the rural atmosphere, with a focus on slow living and environmentally friendly production.
Reviewers highlight the simple, genuine experience and the warm hospitality of the owners. It’s ideal for travelers who want to escape the city and enjoy Tuscany’s countryside without a lengthy tour. This experience is especially suited for those interested in organic, local winemaking.
Bottom Line: A relaxing, authentic tasting experience for those wanting to connect with Tuscany’s rural wine tradition.
10. Arezzo: Tuscan Vineyard Picnic with Wine and Local Food
Finally, this 1.5-hour picnic among the vineyards offers a laid-back way to enjoy Tuscany. You’ll feast on a basket of local specialties, sip wine, and relax in the vineyard’s scenic surroundings. You can choose your picnic spot, whether under a shady tree or in the sun, and stroll through the vines afterward.
It’s a perfect experience for couples or families seeking a casual, scenic lunch with authentic flavors. Reviews note the quality of the local food and wine, which make it a memorable, restful way to spend part of your day.
Bottom Line: Ideal for those wanting a leisurely, scenic picnic experience that combines good food and wine with stunning views.
How to Choose the Right Tour in Arezzo
When selecting your ideal Arezzo experience, consider your budget, how much time you have, and what interests you most. If you love wine, the Brunello Wine Tour or the All Tuscany Wine Tour offer comprehensive tastings. For a culinary adventure, the Cooking class in a Tuscan Villa combines hands-on cooking with local ambiance.
If you prefer cultural walking tours, the Cortona Walking Tour or the Arezzo group walking tour are excellent options. For a relaxing countryside experience, the Vineyard picnic or Tenute di Fraternita provide authentic, scenic moments.
Booking early is advised, especially for private tours and popular experiences. Consider your fitness level and interest focus—whether it’s wine, food, or cultural exploration—and choose the tour that best matches your style.
Final Thoughts
Arezzo offers a broad spectrum of tours and experiences that showcase Tuscany’s wine, food, art, and history. From intimate wine tastings to scenic drives and hands-on cooking classes, you’ll find something to deepen your appreciation of this region. For a rich, authentic experience, the Tour through the vineyards and olive oil tasting in Tuscany is hard to beat, especially if you’re into art and history. Budget travelers might prefer the Walking Tour in Cortona, while lovers of scenic landscapes will enjoy the Brunello Wine Tour.
Whatever your interests, booking early will ensure you secure your spot. Tuscany’s charm is best savored with a well-planned experience—so pick your adventure and prepare for a memorable trip in Arezzo.