15 Of The Best Tours In Arezzo

Arezzo might be famous for its stunning Renaissance architecture and vibrant history, but it’s also a treasure trove for travelers seeking memorable tours. From tasting the finest Tuscan wines amidst rolling vineyards to exploring ancient Etruscan towns on a guided eBike ride, the city offers a rich variety of experiences. We especially like the Tour through the vineyards and wine and olive oil tasting in Tuscany for its intimate setting and engaging storytelling. This experience immerses you into the heart of Chianti Colli Aretini, with a chance to learn about art and history at a villa from 1558 while enjoying tastings. For a more exclusive indulgence, the Private Montalcino wine tour offers a behind-the-scenes look at Italy’s prized Brunello wines.

Arezzo’s diverse offerings make it a perfect base for wine lovers, history buffs, and foodies alike. Whether you want to pedal through classic Tuscan scenery, learn to cook like a local, or simply sip wines in a scenic setting, you’ll find a tour tailored to your interests.

1. Tour through the vineyards and wine and olive oil tasting in Tuscany

At number 1, this vineyard and oil tasting experience offers a delightful taste of authentic Tuscan life. Located near a beautiful Renaissance villa of 1558, the farm is set among the lush vineyards of Chianti Colli Aretini. The tour includes storytelling about the villa’s history, as well as tastings of local wines and olive oils. What makes this tour stand out is its intimate setting—only about an hour and a half long—and the chance to taste fresh Shiraz grapes and learn the art of wine tasting from knowledgeable guides like Virginia. Reviews highlight the engaging storytelling and scenic scenery, making this a perfect introduction for wine enthusiasts and those interested in art and history. The price point of around $40 makes it an excellent value for a personalized, small-group experience.

Bottom Line: This tour suits wine lovers who enjoy short, educational visits with tasting, storytelling, and scenic views—ideal for a relaxed afternoon in Arezzo.

2. Brunello Wine Tour and Val D’Orcia Landscape

Next on our list, this private half-day tour explores the renowned Brunello di Montalcino, Tuscany’s most celebrated red wine. For around $256, you’ll visit a family-owned winery, enjoy tastings of Brunello and other local wines, and explore the breathtaking landscapes of the UNESCO-listed Val d’Orcia. Your guide, Fabrizio, is a sommelier with deep regional knowledge who will customize your experience, making for a truly personalized day. Besides wine, you’ll visit hill towns and historic monasteries, capturing classic Tuscan vistas. Reviewers praise Fabrizio’s expertise and the ability to see sights you wouldn’t find alone, making this tour well worth the investment.

Bottom Line: This tour is perfect for wine connoisseurs and those eager to combine scenic drives with top-quality tastings in an exclusive setting.

3. Cortona – Easy guided eBike tour around the Etruscan City

Number 3 offers an eBike adventure through the charming hilltop town of Cortona. This 2-3 hour tour is suitable for most fitness levels, with a limit of 2-3 riders per guide to ensure comfort. You’ll visit the Fortezza di Girifalco, the Basilica di Santa Margherita, and the serene Eremo Le Celle—each spot offering stunning views and stories of the area’s Etruscan roots. The highlight is the visit to Villa Bramasole, made famous by “Under the Tuscan Sun.” Riders rave about the friendly guides and the ease of e-biking, which lets you enjoy the scenery without exhaustion.

Bottom Line: Ideal for active travelers wanting a light cycling experience combined with cultural and scenic highlights, suitable for all skill levels.

4. Discover Sustainable Wines in a Guided Tour and Tasting

At number 4, this private sustainable wine tour focuses on organic practices at a scenic vineyard near Arezzo. The experience features a tour of the vineyard, an exploration of the eco-friendly cellar, and tastings of three organic wines paired with local cheeses and cured meats. Priced at about $40, it offers a genuine behind-the-scenes look at organic winemaking, appealing to eco-conscious travelers and wine lovers alike. Reviewers appreciate the personal attention and the chance to learn about sustainable practices firsthand, making this tour both educational and delicious.

Bottom Line: Best suited for eco-aware wine enthusiasts looking for an authentic, intimate experience blending wine, food, and sustainability.

5. Cortona Cooking Class

Number 5 is a hands-on culinary experience led by a local chef in Cortona. For approximately $207, you’ll learn to prepare a full Tuscan meal—from antipasto and handmade pasta to dessert—using fresh, organic local ingredients. After cooking, everyone sits down together to enjoy the meal with local wine. Guests praise the friendly atmosphere and the chance to pick up authentic skills while getting a peek into Tuscan culinary traditions. The class is suitable for all skill levels and offers vegetarian options on request.

Bottom Line: A perfect choice for foodies who want to learn practical cooking skills and enjoy a delicious, authentic Tuscan feast.

6. Private Tour: Montalcino Wine Tasting Experience

Number 6 offers a luxurious, private exploration of Montalcino’s famous wineries. For about $406, you’ll visit top estates, explore historic cellars, and taste Brunello di Montalcino along with other fine wines. The tour includes a visit to the Abbazia di Sant’Antimo if desired, and transportation is private, making it ideal for those seeking exclusivity. Reviewers describe it as a “perfect blend of wineries” with an experienced guide elevating the experience. The focus on high-end wine tastings and private transportation makes this a splurge worth considering for serious wine collectors.

Bottom Line: Best for connoisseurs who want a high-end, fully customized wine journey across Tuscany’s best wineries.

7. Cellar Tour & Wine Tasting

This more affordable wine tour combines a visit to Villa Fabbriche’s vineyards and wine cellar with a tasty local lunch. For $57, you get an intimate look at the production of both red and white wines, plus a meal of local meats, cheeses, and bruschetta. The reviews highlight the knowledgeable host and the delicious food paired with excellent wines. It’s perfect for those who want a relaxed, informative experience that includes food and wine in a picturesque setting.

Bottom Line: Great for travelers seeking a personal, budget-friendly wine day with a delicious local meal.

8. Cortona – eBike tour and wine tasting in the Val di Chiana [+40€]

A longer, full-day eBike and wine experience designed for enthusiastic cyclists. Starting 20 minutes from Cortona, this 5-6 hour tour includes riding through rolling hills, vineyards, and olive groves, with stops at a winery for tastings and lunch. The guide, Valentino, is acclaimed for his friendliness and local knowledge. Reviews mention the ease of riding, the spectacular scenery, and the delicious wine and food afterward. It’s suited for active travelers who want a comprehensive taste of the countryside.

Bottom Line: Perfect for fit, outdoor-minded travelers who want to combine cycling with wine tasting in a scenic setting.

9. Castiglion Fiorentino – eBike tour in the Tuscan countryside

Number 9 features a guided eBike tour through Castiglion Fiorentino’s countryside, combining solitude and scenery. For about $159, you’ll discover untouched nature, iconic views, and the medieval Montecchio Castle. Guides like Valentin are praised for their safety-first approach and knowledge. The ride is gentle, making it accessible for most riders, and it offers a chance to enjoy Tuscany’s peaceful beauty away from crowded tourist spots.

Bottom Line: Ideal for casual cyclists who want a scenic, educational ride through Tuscany’s quiet hills.

10. Private Tuscany Cooking Lessons with a Professional Chef

Number 10 offers a personalized cooking class at Villa Il Poggetto for around $138. Led by Chef Fabrizio, the class uses organic ingredients from the estate, focusing on authentic Tuscan dishes like pasta and lemon chicken. Afterwards, everyone dines together with wine, and you receive a recipes booklet. Reviewers highlight Fabrizio’s friendly guidance and the quality of both the experience and the food. Perfect for those wanting to take home not just photos but new culinary skills.

Bottom Line: Excellent for food lovers eager to deepen their knowledge of Tuscan cuisine with a talented local chef.

11. Pienza – Ebike tour for a full immersion in Val d’Orcia

This eBike tour from Pienza takes about 3.5 hours, exploring the iconic landscapes of the UNESCO World Heritage site. Starting in Pienza, you will visit the Roman hot springs at Bagno Vignoni and travel through the picturesque valleys of Val d’Orcia. The tour is praised for Roberto’s professionalism and the stunning views, with riders describing the experience as unforgettable. It’s suited for active travelers who want a comprehensive, scenic day on two wheels.

Bottom Line: Ideal for those who want an immersive, scenic experience through some of Tuscany’s most famous vistas.

12. Rent with driver

For ultimate convenience, this car-with-driver service provides tailored transportation. Whether you want a quick transfer or a full-day exploration, professional drivers are ready to make your trip stress-free. With prices around $119 per person, it’s great for travelers who prefer comfort and flexibility without the hassle of driving.

Bottom Line: Best for those seeking personal, flexible transport without worrying about navigation.

13. Cortona Private Guided Tour

Number 13 offers a private walking tour of Cortona, the setting of “Under the Tuscan Sun.” For around $308, you’ll explore Piazza della Repubblica, Palazzo del Capitano, and other landmarks with a personal guide. This tour includes fun stories about the film and its filming locations, making it perfect for fans of the movie or those interested in Etruscan and medieval history. Reviewers note the guide’s enthusiasm and knowledge, which vividly bring the town’s stories to life.

Bottom Line: A short, personalized exploration ideal for travelers wanting a deep dive into Cortona’s past and its cinematic fame.

14. Wine & Oil Tasting Experience

At about $24, this family-run vineyard tour emphasizes tradition. You’ll see the vineyards, explore the cellar, and taste six wines, including Vin Santo and several reds, alongside local cheeses and oils. Reviewers comment on the warmth of the host and the high-quality products. It’s perfect for those on a budget who want a relaxed, authentic taste of Tuscan wine and food.

Bottom Line: Best for travelers seeking an affordable, authentic family experience with a focus on wine and olive oil.

15. Val D’Orcia Dreaming!!

Finally, this full-day tour (about 4 hours) is led by a local who knows the region intimately. Starting in Pienza, visiting Bagno Vignoni, and crossing the scenic Val d’Orcia via secret dirt roads, the experience offers a personalized touch, storytelling, and plenty of photo opportunities. Reviewers praise the guide’s hospitality and the unforgettable landscapes, perfect for those wanting a curated, in-depth visit.

Bottom Line: Best suited for travelers wanting an insider’s perspective on Tuscany’s most beautiful landscapes with plenty of time to enjoy the scenery.

How to Choose the Right Tour

When selecting a tour in Arezzo, consider your budget, interests, and activity level. Wine lovers might prefer the Brunello and Montalcino or Montalcino private experience, while foodies should look at the Cortona cooking class. For scenic outdoor adventures, the eBike tours and countryside rides are excellent choices, especially if you enjoy cycling.

If convenience and comfort are your priorities, the rent with driver provides flexible transportation, or opt for the private guided tours for a personalized experience. Booking early is advisable, especially in high season, to secure your preferred dates and guides.

Arezzo has more than enough variety to suit all kinds of travelers: passionate wine enthusiasts, culinary explorers, history aficionados, or outdoor adventurers. Whether you opt for a quick tasting, a scenic eBike ride, or a full-day private tour, you’ll find that the city’s offerings are as warm and inviting as its Tuscan landscapes. Take the time to pick the experience that fits your style, and book early—these tours fill up fast!