Arezzo may not be the first Italian city that springs to mind when planning a wine tour, but it’s actually a fantastic starting point for exploring Tuscany’s rich viticultural landscape. Its proximity to renowned wine regions like Chianti and Montalcino makes it a smart base for wine lovers seeking authentic experiences away from tourist crowds. We particularly appreciate tours that combine historic charm with hands-on tastings, like the Tour through the vineyards and wine and olive oil tasting in Tuscany, where you get a taste of both art and history along with your wine.
Some tours focus on the well-known classics—think Chianti and Brunello—while others take you into the countryside for a relaxed, rustic experience. Whether you want a quick tasting, a full day of sightseeing, or a scenic picnic among the vines, there’s something in Arezzo for every wine enthusiast.
1. Tour through the vineyards and wine and olive oil tasting in Tuscany
This 1.5-hour experience offers an intimate look at a Tuscan vineyard near a Renaissance Villa of 1558, with plenty of stories about the estate’s past. The farm is situated close to Arezzo and provides an environment where you can learn about both wine and olive oil production, making it ideal for visitors interested in more than just tasting.
Led by Virginia, whose engaging storytelling brings the vineyard’s history to life, this tour includes tasting a variety of wines paired with local cheeses and prosciutto. Visitors rave about the knowledgeable and entertaining guide and the chance to taste fresh Shiraz grapes. The scenic setting, combined with the chance to learn about Tuscan art and history, makes this experience unique. It’s perfect for those who want a short, immersive introduction to the region’s flavors and traditions without breaking the bank.
Bottom line: A charming, affordable option that combines history, art, and authentic wine tasting, ideal for small groups or families wanting a relaxed afternoon.
2. Brunello Wine Tour and Val D’Orcia Landscape
For around $255, this private half-day tour hits the sweet spot for those seeking a deeper dive into Tuscany’s wine and scenery. Starting with a pickup at your hotel, the tour takes you off the beaten path to visit a family-owned winery, where you can taste Brunello di Montalcino, considered one of Italy’s best wines. The guide, Fabrizio, a trained sommelier, offers personalized insights, making this tour especially suited for wine aficionados.
Beyond the winery, the tour explores the stunning Val d’Orcia, a UNESCO World Heritage site famous for its rolling hills, historic hill towns, and medieval monasteries. Guests love Fabrizio’s expert commentary and the chance to see Tuscan landscapes as beautiful as the wine itself. The tour’s focus on behind-the-scenes wine production and scenic drives makes it ideal for those wanting a luxury, personalized experience.
Bottom line: Perfect for serious wine lovers and scenery seekers, this private tour offers a tailored experience that balances wine tasting with breathtaking views and cultural highlights.
3. Arezzo Experience: Winery Tour and Wine Tasting
This 2-hour guided tour offers a taste of local Tuscan wines with a focus on tradition and history. At Azienda Villani, just outside Arezzo, you’ll explore the winery and sample three different wines, complemented by a cured meats platter and extra virgin olive oil tasting with bruschetta. The experience is intimate and relaxed, making it suitable for small groups or couples.
Claudia, the guide, is praised for her warm welcome and engaging storytelling, sharing insights into the estate’s history and the winemaking process. Guests appreciate the chance to taste ancient wines with modern flavors, and the combination of food and wine enhances the experience beautifully. The winery’s location in the Tuscan hills offers a peaceful setting, perfect for those who want a short but meaningful introduction to regional wines.
Bottom line: Great for a quick, authentic taste of Tuscany’s wine and culinary culture, this tour balances education with delicious local products.
4. All Tuscany Wine Tour
If you’re curious about multiple wine regions in Tuscany, this two-hour tour offers a comparative tasting of Brunello di Montalcino, Chianti Classico, Bolgheri, plus three Super Tuscans from Villa La Ripa. The highlight? The exclusive access to a wine cellar adjacent to a Renaissance villa, giving you a glimpse into Tuscany’s best wines in a refined setting.
This tour is especially valuable for those who want to understand regional differences and taste a curated selection of top-tier wines. The small business providing the experience emphasizes quality over quantity, ensuring each wine is carefully selected. Guests rave about the unique tasting experience that highlights the diversity of Tuscany’s wine styles.
Bottom line: A solid choice for wine enthusiasts eager to sample multiple regions and styles in a short session, with the added bonus of an elegant setting.
5. Tenute di Fraternita – Wine tasting in the Arezzo countryside
This 1.5-hour experience takes you to a working farm in the Arezzo countryside, where you can taste organic, environmentally-friendly wines in an authentic rural setting. The focus here is on tradition and simplicity, offering a taste of slow living in Tuscany.
The winery’s ambiance is unpretentious and welcoming, perfect for travelers interested in organic farming and authentic local production. The owners’ commitment to environmentally friendly practices adds a meaningful layer to the tasting. Reviewers mention the authenticity and the informative guide, making this a valuable experience for those who want a less commercialized wine tasting.
Bottom line: Ideal for eco-conscious travelers and those seeking a genuine connection to Tuscan rural life.
6. Arezzo: Tuscan Vineyard Picnic with Wine and Local Food
For just $50, this 1.5-hour picnic experience offers a relaxed way to enjoy Tuscany’s scenic vineyards. You’ll feast on a basket of local specialties and wine, choosing your perfect spot whether in the shade or sun. The setting allows you to stroll through the vines and breathe in the country air, creating a memorable, laid-back afternoon.
This tour is perfect for travelers who want a casual, scenic experience with good food and wine in a beautiful environment. The focus on local specialties and outdoor relaxation makes it suitable for families, couples, or anyone who prefers a less structured activity.
Bottom line: A great pick for those wanting to combine good food, wine, and scenery in a casual setting, ideal for a laid-back Tuscan afternoon.
How to Choose the Right Wine Tour in Arezzo
When selecting your perfect wine experience, consider your budget, available time, and your specific interests. If you’re after a quick taste and historical stories, the Tour through the vineyards and wine and olive oil tasting in Tuscany offers great value. For a luxury, personalized experience, the Brunello wine tour provides customization and scenic beauty.
If you prefer organic, rural settings, the Tenute di Fraternita is a strong choice, while the All Tuscany Wine Tour suits those eager to compare regional styles. Budget travelers and families may enjoy the Vineyard picnic, which combines scenery with casual food and drink.
Book your tour early—especially the private options—and plan according to your interests, whether it’s focused on history, scenery, organic practices, or multiple regions.
Arezzo offers a surprising range of wine experiences that go beyond the usual. Whether you prefer a quick tasting, a scenic drive, or a slow picnic in the vines, you’ll find options that suit your style. For a rich, memorable visit, consider combining one of these tours with the city’s art and history sites—Arezzo is full of surprises. Don’t wait too long—Tuscan wine waits for no one.