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Discover Assisi and Cortona on this private, guided day trip from Florence, featuring stunning views, expert guides, and flexible free time for authentic experiences.

Our review of the Full Day Private Guided Tour to Assisi and Cortona from Florence offers a well-rounded look at this highly-rated experience. Designed for those who want to explore two iconic Italian towns comfortably and authentically, it combines guided visits with free time, all in a private setting. One of the biggest perks? Traveling in your own air-conditioned minivan means avoiding crowded group buses and sticking with your preferred pace.
What we especially love about this tour is how it balances guided insights with personal exploration. You’ll get a meaningful look at Assisi’s famous basilicas with a professional guide, plus ample free time to soak in the town’s peaceful charm. Cortona’s captivating views and medieval streets feel even more special when you’re not rushed. A possible consideration? Since the Basilica di San Francesco is closed on Sundays, this tour is best scheduled on other days to see its interior. This trip suits curious travelers looking for a flexible, intimate experience in Italy’s beautiful countryside.

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The tour kicks off early at 9:00 am from Piazza dei Cavalleggeri in Florence, a central location easy to reach whether you’re staying in the city or nearby. Traveling in an air-conditioned minivan makes all the difference—especially when navigating the rural roads of Umbria and Tuscany. The comfort and quiet allow you to relax or even catch a quick nap during the drive, which, depending on traffic, usually takes around 1 to 1.5 hours to reach Passignano sul Trasimeno.
The first stop is a quick 30-minute visit to Passignano sul Trasimeno. This charming lakeside village is the perfect start, offering a snapshot of rural Italy with its cobbled streets, vibrant waterfront restaurants, and medieval fortress overlooking Lake Trasimeno. Travelers have praised this stop for its scenic beauty and relaxing atmosphere, often noting how it provides a nice breathing space before the more intense sightseeing begins.
You won’t spend much time here, but it’s enough to snap some photos, breathe in the fresh air, and maybe browse a local shop or cafe. It’s a good way to ease into the day without feeling rushed. One reviewer mentioned that this village’s medieval architecture and scenic views made it a highlight, even in its brief visit.
Next up, the star of the day—Assisi, known globally as the birthplace of Saint Francis. The highlight here is a guided tour of the Basilica di San Francesco, which is a UNESCO World Heritage Site. The basilica is famous for its stunning frescoes by Giotto and Cimabue, illustrating the life of Saint Francis and other biblical stories.
However, a crucial point to keep in mind is that the basilica is closed on Sundays, so if you’re planning this tour on a Sunday, you won’t be able to enter the basilica’s interior. Instead, you’ll enjoy the exterior views and a walk around the town, soaking in its medieval charm.
The guided portion lasts about an hour, during which your guide will share stories about Saint Francis, the architecture, and the art that adorns the basilica. Reviewers like Barbara noted that their guide was “everything you might want,” making the visit meaningful and insightful. She added that they promised to return to spend more time, reflecting how much she appreciated the depth of the guide’s knowledge.
Following the guided tour, you’re granted one hour of free time to wander Assisi at your own pace. Some visitors like Paul emphasize that this free time allowed them to visit other local sites, shop for souvenirs, or simply enjoy a coffee in the quaint cafes. Assisi’s winding streets, ancient stone buildings, and peaceful vibe make it ideal for a relaxed exploration.
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After lunch (not included), the journey continues to Cortona, made famous by the book Under the Tuscan Sun. With two hours of free time, you’ll have plenty of opportunity to explore its narrow, winding streets, visit historic churches like the Duomo, or simply enjoy the breathtaking panoramic views over Val di Chiana.
Cortona’s atmosphere is often described as rustic and timeless. Its medieval walls and Etruscan roots shine through as you stroll. Visitors, including Andreas, mention how the views from Cortona are stunning, and the town’s peaceful vibe makes it a perfect spot for a leisurely walk and some authentic photos.
The tour wraps up back at the original meeting point in Florence around late afternoon, giving you a full, enriching day without feeling overly rushed. The convenience of having your transportation included means you won’t have to worry about navigating local buses or train schedules, and the private aspect allows for flexible pacing.

One of the strongest points is the combination of guided tours and free time. The professional guide’s insights add historical and cultural context that enriches your understanding of the sites. Yet, the free periods in Assisi and Cortona let you explore personal interests—whether that’s visiting a local artisan’s shop, taking photos, or simply soaking up the atmosphere.
Travelers consistently praise the private setting. Unlike large group tours, this allows for a more personal experience, where you can tailor your time and ask questions freely. The air-conditioned minivan offers comfort on what can be a long day, especially during warmer months.
Giacomo, the guide praised in a review, made the day special with his friendly demeanor and deep knowledge. Guests felt like they were exploring with a trusted friend who shared stories and tips, making the experience more memorable.
From Passignano sul Trasimeno’s lake vistas to Cortona’s panoramic hilltop views, this tour offers plenty of opportunities for photos and moments of awe. The towns themselves are authentic, not overly touristy, and packed with local charm.
The main consideration is the schedule’s dependence on the basilica’s opening hours. Since the basilica is closed on Sundays, this could impact your experience if you’re visiting on that day. Also, because lunch isn’t included, you might want to budget extra time or plan your own meal in Cortona or Assisi.

This experience is perfect for individual travelers, couples, or small groups who want a personalized, relaxed way to see Assisi and Cortona without the hassle of self-driving or large tours. It’s ideal if you love a mix of guided storytelling and personal exploration, especially if you’re interested in art, architecture, and stunning landscapes. It suits those who prefer private, comfortable transportation over crowded buses and want the flexibility to spend more time in the towns that catch their interest.
It’s also an excellent choice for travelers with limited time in Florence but eager to experience two of Italy’s most picturesque and culturally significant towns. The tour offers a well-organized yet flexible itinerary that balances sightseeing with leisure.

This full-day private tour provides a rich, comfortable way to explore Assisi and Cortona, blending guided insights with free exploration. The private setting and expert guides make it stand out, especially for those wanting a more personalized experience. The stops at lakeside Passignano sul Trasimeno, the awe-inspiring Basilica of Saint Francis, and the panoramic views of Cortona ensure you’ll leave with a deeper appreciation of Italy’s diverse regions.
While the tour’s convenience and intimate touches come at a premium price, the value lies in the quality of the experience, the flexibility, and the comfort. It’s perfect for travelers who prefer not to rush, want to avoid large crowds, and enjoy authentic moments in Italy’s historic towns.
If you’re looking for a day trip that combines scenic beauty, cultural richness, and personalized service, this tour could be a standout choice.

Is lunch included in the tour?
No, lunch is not included. You might want to bring snacks or plan to dine in one of the towns during free time.
What happens if I visit on a Sunday?
Since the Basilica di San Francesco is closed on Sundays, you won’t be able to see its interior. You’ll still enjoy the exterior views and the town’s ambiance.
How long is the total driving time?
The journey from Florence to Passignano sul Trasimeno typically takes around 1 to 1.5 hours, depending on traffic. The return trip is similar.
Can I customize the tour?
This is a private experience, so you can discuss your preferences with the driver or guide. However, the main itinerary is set, with designated free times.
Is this tour suitable for all ages?
Yes, most travelers can participate. However, keep in mind the walking involved in towns and the need to cover shoulders and knees when visiting religious sites.
What language is the guide?
The driver and guide speak English, ensuring clear communication and insightful commentary.
How far in advance should I book?
It’s recommended to book around 108 days in advance, especially during peak travel seasons, to secure your preferred date and time.
In summary, this private tour offers a perfect blend of guided storytelling and personal discovery, all in the comfort of a private vehicle. It’s well-suited for travelers wanting an authentic, flexible, and scenic day trip from Florence—covering Italy’s spiritual and scenic gems with ease and style.