Arezzo is a treasure trove for travelers who enjoy exploring authentic Italy beyond the usual tourist paths. Known for its stunning architecture, charming streets, and rich cultural layers, Arezzo offers a variety of tours that appeal to different interests. Whether you’re a wine lover eager to taste fine Tuscan vintages, a history buff wanting to walk through ancient towns, or someone seeking a deeper understanding of local art, Arezzo has something to offer. We particularly love the Tour through the vineyards and wine and olive oil tasting in Tuscany for its perfect blend of wine, history, and scenery—plus, tasting fresh Shiraz grapes is a memorable highlight.
If you’re planning your trip, this guide will help you navigate the top options, highlighting what makes each one special, how much they cost, and who they’re best suited for. Whether you want to spend a relaxed afternoon among the vines or explore the streets of Cortona, you’ll find valuable insights here to make the most of your time in this beautiful part of Italy.
Quick Overview
Our list covers six of the best tours in Arezzo, showcasing a mix of wine experiences, historic walking tours, and scenic explorations. For wine lovers, options include the Tour through the vineyards and the All Tuscany Wine Tour, which highlight different regions and styles. History enthusiasts will appreciate the Walking Tour in Cortona, offering a deep dive into Italy’s Etruscan roots. For a more casual, local experience, the Arezzo Experience: Winery Tour combines wine tasting and a guided estate visit. The 2-hour group walking tour offers a quick but insightful look at Arezzo’s architectural and cultural highlights, while the Brunello and Val d’Orcia Tour takes you into Tuscany’s iconic landscapes and renowned wines.
Now, let’s explore each of these tours in detail to help you decide which fits your travel style.
1. Tour through the vineyards and wine and olive oil tasting in Tuscany
This wine and olive oil tasting experience offers a relaxed, 1.5-hour journey into a Tuscan farm located near a stunning Renaissance villa. The farm is part of the Chianti Colli Aretini region, rich with stories about its 1558 origins—perfect for those interested in both wine and art. Your guide will share insights into the vineyard’s history and the traditional methods used in winemaking and olive oil production. You get the chance to taste several local wines, including Shiraz grapes, alongside cheese and prosciutto, making it a flavorful experience.
What makes this tour special is its intimacy and focus on storytelling. Visitors consistently praise Virginia’s engaging narration and her ability to blend history with tasting. The scenery is also a highlight, with rolling vineyards and views of the Renaissance villa. At a very reasonable price, it’s an excellent choice for wine lovers and art enthusiasts wanting a taste of authentic Tuscany in a short time.
Bottom Line: A charming, informative experience perfect for small groups and those wanting a personal touch with local wines and scenic views.
2. Brunello Wine Tour and Val D’Orcia Landscape
At number 2, this private half-day tour combines a visit to a family-owned winery with a scenic drive through the UNESCO-listed Val d’Orcia. For around $255, you’ll enjoy a behind-the-scenes tasting of Brunello di Montalcino, one of Italy’s most acclaimed wines, along with other regional varieties. The tour starts with a pickup from your hotel, so no need to worry about logistics—just sit back and soak in the views.
What sets this experience apart is the opportunity for a personalized visit to a top local winery, guided by someone with extensive knowledge of Tuscan wines, including the sommelier Fabrizio. The drive through Val d’Orcia offers iconic Tuscan vistas—cypress-lined roads, medieval towns, and monasteries—these are the pictures you’ve seen in travel magazines.
Guests often comment on how tailored this tour is, with many praising Fabrizio’s ability to adapt the experience to their interests. It’s ideal for wine connoisseurs and those wanting an immersive day away from crowds, though it requires a moderate level of fitness for walking around the wineries.
Bottom Line: A private, customizable experience that immerses you in the heart of Tuscany’s wine and landscape, perfect for serious wine enthusiasts.
3. Walking Tour in Cortona
If you want to explore an Etruscan hill town, this walking tour of Cortona offers a compact but rich introduction to the city’s most important sights. Lasting about 1.5 to 2 hours, the tour takes you through the main street, the impressive churches, and the ancient Etruscan walls. Starting from Piazza Garibaldi, your guide will share stories of Cortona’s long history, from its origins over 3,000 years ago to its role in Tuscany today.
The highlights include visiting Chiesa San Francesco with its relics and the Duomo di Cortona, where you’ll learn how Italian churches differ in style and purpose. Several reviews highlight guides like Elisona for her deep knowledge and personable manner—she even helps with practical tips like train tickets.
This tour is perfect for history and art lovers who want a manageable and engaging way to understand Cortona’s cultural layers without overloading the schedule. Its price is reasonable, and the small group size means lots of personal attention.
Bottom Line: An informative stroll that uncovers the essential sights of Cortona, ideal for those who want a quick but meaningful overview.
4. Arezzo Experience: Winery Tour and Wine Tasting
At number 4, this Arezzo winery experience combines a guided estate tour with tastings of three different wines from a nearby Tuscan winery. The tour includes a tasting of local wines, complemented by a cutting board featuring cured meats from Azienda Villani, plus extra virgin olive oil and bruschetta. It typically lasts between 1.5 and 2 hours, with flexible starting times.
What makes this experience stand out is its focus on local tradition and history. Claudia, the host, is known for her friendly approach and knowledge about the estate’s wine-making process. Guests appreciate the chance to learn about the estate’s history while sampling wines that have been made in the region for generations.
This tour offers excellent value for those wanting a personalized, relaxed wine tasting without a long drive. It’s especially suited for travelers who prefer a shorter, intimate experience with good food and wine in a beautiful setting.
Bottom Line: A warm, approachable experience that balances wine education with regional flavors—perfect for a relaxed afternoon.
5. 2 hours Arezzo group walking tour
This Arezzo city tour is designed for a quick overview of Arezzo’s most notable sights in about two hours. It covers the city’s architecture, artistic masterpieces, and highlights like the Cathedral’s colorful stained glass. Meeting at Piazza Garibaldi, your guide will lead you through streets rich with history, pointing out key landmarks.
While it offers a condensed look, some reviews note it could include more monuments, such as San Domenico with Ligabue’s crucifix, to deepen the experience. Still, guides like Rita are praised for their knowledge and enthusiasm, making the tour lively and engaging. The tour is a good choice if your time in Arezzo is limited but you still want to get a solid sense of the city.
This tour is best for travelers who want a brief, cultural introduction without too much walking or complexity.
Bottom Line: A brief but insightful introduction to Arezzo’s highlights, great for a quick orientation.
6. All Tuscany Wine Tour
Finally, the All Tuscany Wine Tour offers a comprehensive tasting of three major Tuscan wine regions—Brunello di Montalcino, Chianti Classico, and Bolgheri—compared with three Supertuscans from Villa La Ripa. This 2-hour experience takes place in a small, high-quality winery, allowing for an intimate look at different wine styles and terroirs.
This tour is for those who want to understand the diversity within Tuscany’s wine landscape. The wines are served in the cellar next to a Renaissance villa, which adds a touch of elegance to the experience. The winemaker’s focus on quality, combined with the comparative tasting, makes it stand out. Reviewers appreciate the unique opportunity to taste wines from different regions in a single session.
Ideal for wine enthusiasts eager to deepen their knowledge and taste a broad spectrum of Tuscany’s best wines, this tour provides excellent value for its depth and quality.
Bottom Line: A thorough exploration of Tuscany’s wine regions in one session, suited for serious wine lovers wanting a detailed tasting.
How to Choose
When selecting the right tour in Arezzo, consider your interests, schedule, and budget. If you’re passionate about wine and scenery, the Brunello Wine Tour and Val d’Orcia offers a personalized experience with breathtaking views. For a quick cultural fix, the Arezzo group walking tour provides a solid overview in a short time.
Budget-conscious travelers might prefer the Tour through the vineyards, which combines affordability with authentic scenery and storytelling. Meanwhile, wine aficionados should consider the All Tuscany Wine Tour for its extensive regional comparison and rich tasting.
Timing is also key; weekends fill quickly for popular tours, and booking early guarantees your spot. Think about your fitness level—some tours involve walking on uneven terrain or standing for a while—so plan accordingly.
Final Thoughts
Arezzo and its surrounding regions offer a variety of engaging tours that showcase Tuscany’s beauty, history, and exceptional wines. For those interested in a personalized wine experience, the Tour through the vineyards and All Tuscany Wine Tour are top picks. History lovers will enjoy the Walking Tour in Cortona, which offers a deep dive into Italy’s ancient past.
No matter your preferences, early booking is recommended—these tours fill up fast, especially during peak seasons. Whether you want a quick overview or an in-depth exploration, Arezzo’s tours promise authentic experiences that will enrich your trip and deepen your understanding of Tuscany’s rich culture.