Arezzo is a city that’s rich in art, history, and landscapes, but what makes it truly special for travelers are the tours that bring its surroundings to life. Whether you’re a wine lover eager to taste world-class Brunello, a foodie keen on learning authentic cooking skills, or an adventurer looking to explore on two wheels, Arezzo offers experiences that go beyond the typical sightseeing. The vineyard tours like the Tour through the vineyards of Chianti are popular for their combination of wine, art, and history, set in stunning Tuscan scenery. Meanwhile, the eBike adventures in Cortona and Castiglion Fiorentino offer scenic rides through rolling hills and historic towns, perfect for active travelers.
Our list below highlights the best tours in Arezzo, covering a wide array of interests — from private wine tastings and guided city walks to immersive cooking classes and scenic bike rides. Each offers a unique way to experience Tuscany’s charm, often with highly praised guides, small-group intimacy, and authentic local flavors.
1. Tour through the vineyards and wine and olive oil tasting in Tuscany
This immersive experience takes you into a Tuscan vineyard near a Renaissance villa of 1558 that’s full of stories. For about 1.5 hours, you’ll learn about the production of Tuscan wines and olive oils, taste several varieties, and enjoy the scenery. Virginia, your guide, is praised for her storytelling, making this not just a tasting but a journey into art, history, and tradition.
The highlight is the story of the vineyard’s origins and the lessons in wine tasting, complemented by tasting fresh Shiraz grapes and local cheeses. The reviews speak to its value, with visitors mentioning the knowledgeable guide and the beautiful scenery. For wine lovers and those interested in Tuscan agriculture, this is a warm, educational, and delicious experience.
Bottom Line: Perfect for small groups and those who want a true taste of Tuscany’s viticulture without a hefty price tag.
2. Brunello Wine Tour and Val D’Orcia Landscape
This private, half-day tour offers a deep dive into Brunello di Montalcino, one of Italy’s most prestigious wines. After pickup from Arezzo, you’ll visit a local family-owned winery for a behind-the-scenes tour and tastings of Brunello and other wines, paired with local snacks. The tour continues with a scenic drive through Val d’Orcia, a UNESCO World Heritage site famed for its timeless rolling hills and hilltop towns.
Fabrizio, the guide, is highly rated for his knowledge and personalized approach. Guests love how he customizes the experience based on preferences, making it suitable for both wine novices and connoisseurs. The stunning landscape views combined with exclusive tastings make this tour a favorite for those wanting a refined, intimate wine experience.
Bottom Line: An excellent choice for wine enthusiasts seeking exclusivity and scenic beauty, with a high-quality, personalized touch.
3. Cortona – Easy guided eBike tour around the Etruscan City
This 2 to 3-hour guided eBike tour in Cortona takes you through the famous film location of “Under the Tuscan Sun” and other historic sites. The route includes stops at Villa Bramasole, the Basilica di Santa Margherita, and the Eremo Le Celle – a tranquil sanctuary of Franciscan monks.
Bikes are well-reviewed, and the group size is kept small for comfort and safety. Many visitors comment on the easy ride, beautiful vistas, and informative guides like Alessio and Mario, who share stories about the town’s past. The tour is suitable for riders of most levels, with a relaxed pace that allows for plenty of photo stops.
Bottom Line: A fantastic, active way to discover Cortona’s sights and scenery, especially if you’re into history, movies, and cycling.
4. Cortona Cooking Class
This 4-hour, hands-on cooking class in Cortona is ideal for foodies eager to learn authentic Tuscan dishes. You’ll prepare antipasto, handmade pasta, a second course, and dessert, all under the guidance of a professional chef. After cooking, everyone sits down to enjoy the meal with local wine.
Chef Elena and Cristina are praised for their warmth and clear instructions. The class often receives 5-star reviews for its informality, delicious food, and the authenticity of ingredients. Vegetarian options are available, making it accessible for dietary restrictions. The experience offers both culinary skills and cultural insight.
Bottom Line: Perfect for those who want to bring home Tuscan flavors and enjoy a fun, intimate meal with new friends.
5. Private Tour: Montalcino Wine Tasting Experience
This 8-hour private tour focuses on Brunello di Montalcino, visiting prestigious wineries and cellars for exclusive tastings. Your guide takes you from Arezzo to stunning vineyards, with the optional visit to Abbazia di Sant’Antimo — a beautiful medieval abbey. This tour is tailored to your preferences, with private transportation included.
Guests often mention the personalized service and expert guidance, especially when visiting the top wineries. The focus on quality makes it a worthwhile splurge for serious wine lovers or those wanting a luxury experience. The full-day itinerary offers a comprehensive look at Tuscany’s most celebrated wine and landscape.
Bottom Line: A luxurious, in-depth tasting designed for connoisseurs or those celebrating special occasions.
6. Cellar Tour & Wine Tasting
This 3-hour tour explores Villa Fabbriche, a family-run vineyard outside Arezzo. You’ll visit the vineyards, learn about local wine production, and taste a variety of red and white wines. The experience is complemented by a lunch of local delicacies like cheeses, meats, and olive oil.
Visitors commend the personal attention from the host and the beautiful views of the Tuscan countryside. The tasting includes several wines, making it a good value at around $57.62 per person. It’s ideal for those interested in wine and food pairing, with an authentic, relaxed atmosphere.
Bottom Line: A well-rounded, affordable option for wine and culinary enthusiasts wanting a taste of local life.
7. Cortona – eBike tour and wine tasting in the Val di Chiana [+40€]
![Cortona - eBike tour and wine tasting in the Val di Chiana [+40]](https://mumsdotravel.com/wp-content/uploads/2025/12/cortona-ebike-tour-and-wine-tasting-in-the-val-di-chiana-40.jpg)
This 5-6 hour eco-friendly tour combines cycling, tasting local wines, and exploring the Val di Chiana. Starting near Cortona, you’ll ride through picturesque vineyards, visit a winery for tastings, and enjoy a local lunch.
Guides like Valentino are praised for their knowledge and friendliness, enhancing the experience. The tour suits active travelers who want to combine scenic cycling with culinary delights. The small group size ensures personalized attention, and the discount codes make it a good deal.
Bottom Line: A perfect blend of adventure and relaxation for those wanting to see Tuscany on two wheels with a gourmet touch.
8. Castiglion Fiorentino – eBike tour in the Tuscan countryside
This 3.5-hour ride offers a guided exploration of Castiglion Fiorentino and Monteccio Castle. The route features breathtaking views, serene landscapes, and stops at historic sites. Riders praise the top-quality bikes and friendly, knowledgeable guides.
Suitable for most fitness levels, this tour is ideal for history lovers and nature fans who want an active, scenic experience outside Arezzo. Reviewers mention how the route is easy to follow and full of photo opportunities.
Bottom Line: A relaxed yet scenic way to see Tuscany’s countryside, especially for those interested in medieval towns and historic landmarks.
9. Private Tuscany Cooking Lessons with a Professional Chef
This 4-hour private cooking class at Villa Il Poggetto offers a personalized culinary experience led by Chef Fabrizio. Participants prepare authentic Tuscan recipes using locally sourced ingredients. The class ends with everyone enjoying their homemade meal paired with Tuscan wine.
Guests love how Chef Fabrizio shares insider tips and customizes lessons, making the experience both fun and educational. The small-group format ensures plenty of hands-on involvement and personal attention.
Bottom Line: An ideal choice for passionate foodies who want to learn authentic cooking techniques in a welcoming setting.
10. Pienza – Ebike tour for a full immersion in Val d’Orcia
Starting from Pienza, this 3.5-hour guided eBike tour takes you through the iconic landscapes of Val d’Orcia. You’ll visit small towns, enjoy panoramic views, and explore local farms. Roberto, your guide, is praised for his professionalism and knowledge, helping you capture the essence of this UNESCO site.
The tour is suited for active travelers interested in photography and nature, with plenty of stops for pictures and snacks. The small group size makes it a personalized experience.
Bottom Line: Perfect for those wanting a scenic, active day immersed in Tuscany’s most famous landscapes.
11. Rent with driver
If you prefer not to drive but still want flexibility, this chauffeur service offers private car rentals with drivers for any duration from an hour to a full day. It’s perfect for customized transfers or day trips to vineyards, towns, or landmarks. The professional drivers ensure a safe, relaxing journey.
Ideal for travelers with specific destinations or those who want to avoid parking and navigation worries, this service complements any of the tours listed here.
Bottom Line: Best suited for travelers needing personalized transportation without the hassle of self-driving.
12. Cortona Private Guided Tour
This 2-hour private walk with a local guide offers an in-depth look into Cortona’s Etruscan and medieval roots. You’ll visit Piazza della Repubblica, Palazzo del Capitano, and the Teatro Signorelli. Hear stories about “Under the Tuscan Sun” and the town’s fascinating past.
Reviews emphasize the guide’s passion and knowledge, which bring the town’s history and charm alive. Private tours are customizable, making them suitable for personalized interests, including photography or history.
Bottom Line: A memorable, intimate way to discover Cortona’s rich past and visual beauty.
13. Wine & Oil Tasting Experience
This private, casual tasting takes place at a family-run vineyard near Castiglion Fiorentino. It includes a tour of the vineyards, cellars, and the Vin Santo production area, plus tastings of six wines and estate-grown extra virgin olive oil. Expect a relaxed, authentic atmosphere.
Reviewers enjoy the personal attention and the chance to taste multiple wines alongside local cheeses and salami. The price point is very reasonable at just $23.72 per person, making it accessible for a quick, authentic experience.
Bottom Line: Great for foodies seeking a laid-back, authentic introduction** to Tuscan wines and oils.
14. Val D’Orcia Dreaming!!
A personalized full-day tour led by someone with deep roots in the region, this experience offers customized visits to Pienza, Bagno Vignoni, and scenic drives through Val d’Orcia. The guide’s local relationships and fluent English help craft a memorable day, including gourmet stops and stunning photo opportunities.
Rated highly for personalized service and deep knowledge of Tuscany, this tour suits travelers wanting a tailored, intimate experience.
Bottom Line: Ideal for luxury seekers or those wanting a bespoke day exploring Tuscany’s iconic landscapes.
15. Personal Chef – Cooking class at your villa
For travelers staying in a villa, this bespoke cooking experience offers a private chef who prepares authentic Tuscan meals right at your accommodation. The chef takes care of shopping, cooking, and serving, allowing you to relax and enjoy your surroundings.
Guests appreciate the personalized service and the opportunity to learn about regional ingredients. It’s perfect for special occasions or those who want a high-end, stress-free culinary experience.
Bottom Line: Excellent for luxury travelers seeking private, customizable Tuscan cuisine in their own villa.
How to Choose the Right Tour in Arezzo
When selecting your perfect experience, consider your budget, interests, and physical activity level. For example, if you’re a wine enthusiast, the Brunello Wine Tour offers a comprehensive, exclusive taste of Tuscany’s best. If you’re more into culinary arts, the Cortona Cooking Class or the Private Tuscany Cooking Lessons provide hands-on opportunities to learn regional recipes.
Active travelers might prefer eBike experiences like the Cortona guided eBike tour or the Val di Chiana eBike tour, while those seeking a relaxed day can opt for private guided tours or rent with driver services for maximum flexibility.
Booking early is recommended, especially for popular tours during high season, and always check for discount codes or customization options to tailor your experience.
Final Thoughts
Arezzo and its surroundings present an incredible variety of tours that satisfy culinary, cultural, and adventurous appetites. From tasting world-class wines like Brunello to exploring ancient towns on eBikes, there’s something for all. If you’re into gastronomy, the cooking classes stand out, while wine connoisseurs will appreciate the exclusive tastings and private estate visits.
For a relaxed, culture, private guided tours and local experiences like the Wine & Oil Tasting offer unforgettable memories. No matter what you choose, booking early and tailoring your experience to your interests will ensure you get the most out of your time in this beautiful corner of Tuscany.
