Arezzo is a treasure for those who love wandering through towns where every cobblestone and church tells a story. Unlike many Tuscan cities that cater mainly to car travelers, Arezzo’s compact streets and rich architectural layers invite exploration on foot. Whether you’re interested in uncovering its medieval charm, admiring stunning views, or delving into Etruscan roots, a walking tour is the perfect way to experience this vibrant town. Among the options, the 2-hour group tour offers a lively introduction, while the private tours give you a personalized, in-depth look—ideal for those craving an intimate experience or traveling with family. For lovers of history and photography, the Arezzo private walking tour is a standout.
Below, you’ll find a curated list of the best walking tours in Arezzo, each with unique strengths. From guided group explorations to private journeys through historic streets, these options help you choose the perfect way to soak in the city’s sights.
1. Walking Tour in Cortona
At number 1, this Walking Tour in Cortona offers a rich 1.5 to 2-hour stroll through one of Tuscany’s most picturesque hill towns. While technically outside Arezzo, it’s a favorite for visitors who want a compact, expert-led introduction to Cortona’s Etruscan walls, main street, and notable churches. The tour visits the Chiesa San Francesco, holding relics of Italy’s religious history, and the Duomo di Cortona, where you’ll see the differences in Italian church architecture firsthand.
What makes this tour stand out is its focus on 3000 years of history, weaving stories from ancient Etruscans to modern times. Guides like Elisona bring a personable touch, making the past come alive. Reviews praise her knowledge and kindness, with many mentioning how her insights add depth to the experience. The tour includes admission tickets for key sites, making it not just educational but also convenient.
Bottom Line: This tour is perfect for travelers who want a quick, engaging overview of Cortona’s highlights, especially if you’re short on time but want rich storytelling and scenic views.
2. Cortona private walking Tour
Number 2 on our list is the Cortona private walking tour, which lasts about 2.5 hours. This personalized experience is ideal for those who want to explore Cortona’s main sights at their own pace. You’ll visit the Duomo di Cortona, the Piazza Signorelli, known for its beautiful architecture, and the Palazzo Casali, home to important museums and archives.
The tour’s highlight is a deep dive into Cortona’s Etruscan origins, alongside insights into its medieval and Renaissance phases. Guides like Catia and Debora are praised for their knowledgeable and personable approach, making history accessible without feeling rushed. Inside the churches and monuments, you’ll see works by famous artists, adding an artistic dimension.
Guests especially enjoy that this tour offers entry to key sites, giving a richer experience. It’s suited for travelers who love history, art, and a flexible itinerary with a trusted guide.
Bottom Line: Perfect for those wanting an in-depth, customizable tour with expert narration in a town made famous by Under the Tuscan Sun.
3. Arezzo Private walking tour
Number 3 is the Arezzo Private walking tour, which concentrates on the medieval core of Arezzo. Over two hours, your guide takes you through the Cathedral, Piazza Grande, and the Badia di S. Flora e Lucilla. This tour emphasizes Arezzo’s architectural highlights and historic shops—a great way to see how the city’s past lives on in everyday life.
Guests appreciate the personalized attention and the guide’s ability to blend factual history with lively storytelling. The tour covers important sites like Palazzo Pretorio, which is now a library, and includes plenty of photo opportunities. The inclusion of admission tickets means fewer surprises and more time appreciating the sights.
This tour is suited for travelers who want to experience Arezzo’s medieval charm intimately, especially if they enjoy shopping or are curious about local culture.
Bottom Line: A straightforward, well-rounded private option for exploring Arezzo’s main sights with a knowledgeable guide.
4. Private Walking Tour of Pienza with Licensed Tour Guide
Number 4 is the Private Walking Tour of Pienza, focusing on Pienza, a UNESCO World Heritage site famous for its Renaissance architecture. During this 2-hour tour, your guide will explore Pius II’s ambitious urban planning efforts, highlight the main square, and reveal secrets about its shape and hidden messages.
Guests love that the tour includes a Pecorino cheese tasting and offers views over the Orcia Valley, perfect for photography. The guide’s passion makes this tour especially memorable, and the focus on Pienza’s transformation from medieval village to Renaissance masterpiece** is a highlight. It caters to those interested in architecture, local gastronomy, and panoramic vistas.
This tour offers excellent value for those wanting a comprehensive look at a small but significant town, with plenty of insider tips.
Bottom Line: Ideal for travelers who want an in-depth, personalized experience of Pienza’s history, architecture, and culinary delights.
5. Cortona Private walking Tour under the Tuscan sun
Number 5 on our list is the Cortona Private walking Tour under the Tuscan sun, which emphasizes Cortona’s charm through its scenic viewpoints and famous film connections. This 2-hour tour takes you to Piazza Signorelli, the Duomo, the Fortezza di Girifalco, and the Porta Bifora.
The guide shares stories about Frances Mayes’ novel and film, making this tour especially appealing to fans of Under the Tuscan Sun. Tour highlights include spectacular views of the countryside and insights into Cortona’s Etruscan and medieval layers. Guests mention the guide’s passion and extensive knowledge, which bring the city’s history to life.
This tour is best suited for those seeking a personalized, story-rich experience with great photo opportunities and a relaxed pace.
Bottom Line: Perfect for fans of Under the Tuscan Sun or anyone wanting a scenic, story-driven tour of Cortona.
6. 2 hours Arezzo group walking tour
Finally, the 2-hour Arezzo group walking tour offers a lively overview of Arezzo’s main sights. With a focus on architecture and art, this tour highlights the Cathedral’s paintings and stained glass and visits Piazza Grande and the Badia of S. Flora.
Rated 4.4 out of 5, travelers find the tour friendly and informative, though some mention it could include more sites like San Domenico. The guide’s approachability and knowledge make it a good choice for first-time visitors wanting a quick but comprehensive introduction.
While this tour offers a great value, it may feel a bit rushed if you’re eager to explore every corner. It’s best for travelers with limited time who want a social, energetic group experience.
Bottom Line: Suitable for those new to Arezzo who want a friendly introduction without a hefty time commitment.
How to Choose the Best Walking Tour in Arezzo
When selecting your ideal walking tour, consider your budget, interest level, and pace. For a personalized experience that dives deep into Pienza’s architecture or Cortona’s panoramic views, the private options (Cortona private walking tour and Pienza tour) offer tailored insights but come at a higher price. If you’re after a quick overview and want to meet fellow travelers, the Arezzo group tour provides great value.
Think about your physical fitness—most tours involve walking on cobblestone streets and inclines. The best time for walking tours in Tuscany is during spring or early fall when weather is moderate. Booking in advance is advised, especially for private tours, to secure your preferred time and guide.
Final Thoughts
Arezzo and its nearby gems like Cortona and Pienza offer a variety of walking experiences that suit all types of travelers. Whether you’re looking for a quick introduction, an in-depth private exploration, or a scenic adventure based on literary fame, this list covers the best options. For history lovers, the private tours provide detailed insights, while group tours are perfect for socializing and soaking in the atmosphere.
If you want to make the most of your time in Tuscany, consider booking early—these tours fill up quickly in peak season. Whichever you choose, a walk through Arezzo’s streets promises a memorable blend of art, architecture, and authentic Italian charm.