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Discover Cortona with a private 2-hour walking tour led by expert guides, exploring historic sites, stunning architecture, and iconic spots from "Under the Tuscan Sun."
Experience the charm of Cortona through a private walking tour that lasts approximately 2 hours. Priced at $185.22 per person, this tour offers an intimate look at one of Tuscany’s most beautiful hilltop towns. Led by knowledgeable guides, the tour takes you through key landmarks, providing insights into Cortona’s Etruscan origins, medieval heritage, and Renaissance splendor. The tour is designed for most travelers, with the highlight being the opportunity to explore famous sites such as Piazza Signorelli, the Duomo, and Fortezza di Girifalco. With group discounts available and the convenience of a mobile ticket, this experience is both flexible and accessible.
While the tour is concise, its focus on major landmarks and the history of Cortona makes it ideal for visitors wanting a well-rounded overview in a short span. The personalized nature of this private experience ensures you receive tailored attention from the guide—perfect for those eager to learn about the town’s Etruscan roots and Renaissance art. A potential consideration is the price point, which reflects the exclusivity of a private guide, making it most attractive to those seeking a personalized, in-depth exploration of Cortona.


The tour begins at Piazza Signorelli, a lively hub named after the notable Renaissance painter. Here, the Etruscan Academy Museum showcases a captivating collection of bronze, ceramic, and funerary artifacts. This stop offers a glimpse into Cortona’s ancient past and its Etruscan heritage, which dates back centuries. The museum’s collection provides context for the city’s long history, and the free admission makes it accessible for all.
Strolling through the square, visitors appreciate the blend of historical artifacts and medieval architecture that surrounds the square, setting the tone for the rest of the tour. The guide shares stories about the Etruscan walls that still frame the town, giving depth to Cortona’s layered history.
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Next, the tour moves to Piazza del Duomo, home to the Cathedral of Santa Maria Assunta. This 14th-century gothic church stands prominently and is built atop an earlier church, with some remnants visible on its facade. The Renaissance architectural style of the cathedral reflects Cortona’s artistic heritage, and the guide explains its construction by followers of Giuliano da Sangallo.
Visitors can appreciate the monumental complex comprising the cathedral and the Bishops Palace, which together shape the square’s historic atmosphere. The free admission allows for a closer look at the church’s details and artistic elements.

Climbing up to Fortezza di Girifalco offers a dramatic view of Cortona from its highest point. Built in 1561 under the direction of Gabrio Serbelloni at the behest of Grand Duke Cosimo I dei Medici, the fortress is a significant example of military architecture.
The outlook from the fortress provides panoramic views of the Tuscan countryside, with cypresses, vineyards, and olive groves spread out below. The guide shares insights into the fortress’s role in Cortona’s defense and its historical importance, enriching the experience of the stunning vistas.

The tour includes a visit to Porta Bifora, also known as Ghibellina. This double-arched entrance dates back to Etruscan times and is the oldest surviving gateway of the town. Its name, “Bifora,” references the double entrance design that was characteristic of Etruscan architecture.
Standing at this ancient gate, visitors gain a tangible connection to Cortona’s pre-Renaissance history. The guide explains the significance of this structure as part of the original city walls, offering a fascinating look at the town’s archaeological layers.

The tour starts at Piazza Garibaldi in Cortona and lasts approximately 2 hours. It is a private experience, meaning only your group participates, providing an intimate and tailored atmosphere. The meeting point is conveniently located near public transportation, making it easy to access.
The tour includes free admission to the museums and landmarks visited during the walk, with the option for discounts if booked in a group. The mobile ticket allows for easy check-in, and the booking is flexible, with full refunds available if canceled at least 24 hours in advance.
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What sets this private Cortona walking tour apart is the knowledgeable guidance and focus on major landmarks. The guides are praised for their friendly and eager to share their love of Cortona’s history and art. Their attention to detail makes the experience engaging, whether explaining Etruscan origins or Renaissance architecture.
The emphasis on famous sites like Piazza Signorelli, the Duomo, and Fortezza di Girifalco ensures visitors see the most important aspects of Cortona, even in a short timeframe. This tour is particularly suited for those who want a personalized overview and insider insights into the town’s historical significance.

While the 2-hour duration allows for an efficient exploration, visitors should be prepared for some walking and standing. The stops involve staircases and uneven surfaces, and walking routes highlight outdoor settings with spectacular views. The price point reflects the private guide service, making it ideal for travelers seeking a more personalized experience.
Given its focus on major landmarks and history, this tour suits history buffs, art lovers, and anyone eager to understand Cortona’s past comprehensively. It may be less suitable for those seeking a culinary experience or hands-on activities—but those interested in the town’s heritage will find this tour particularly rewarding.
This private walking experience offers a compact yet comprehensive look at Cortona’s most significant sites. The guides’ expertise and personalized approach make it a strong choice for visitors wanting to maximize their time and gain insights into the town’s Etruscan, medieval, and Renaissance history.
The free admission to museums and landmarks, combined with the flexibility of private booking, provides value and comfort. While the cost may be a consideration for some, the depth of knowledge and customized attention justify the price for those seeking an authentic and insightful Cortona experience.
“Laura was fantastic! She is friendly, knowledgable and eager to share her love of Cortona with her guests. We appreciated her attention to detail a…”
Is this tour suitable for all ages?
Yes, most travelers can participate, though some walking and outdoor activity are involved. It’s best suited for those comfortable with walking and standing.
Can I cancel the tour if my plans change?
Yes, full refunds are available if canceled at least 24 hours before the scheduled start.
Where does the tour start and end?
It begins at Piazza Garibaldi and ends back at the same location, making it easy to continue exploring Cortona afterward.
Do I need to book in advance?
Yes, the tour is typically booked 22 days in advance on average, ensuring availability and planning.
Are the landmarks included in the tour accessible?
Yes, the landmarks have free admission, and the guide provides insights into each site’s significance.
What makes this private tour different from group experiences?
The private setting allows for a more personalized pace and direct interaction with the guide, tailored to your interests.