Full Day Private Guided Tour to Assisi and Cortona from Florence

Discover the Charm of Assisi and Cortona on a Private Day Trip from Florence

Taking a full-day private tour from Florence to Assisi and Cortona promises a blend of breathtaking scenery, cultural treasures, and authentic Italian ambiance—all without the hassle of public transport or large group tours. This experience is ideal for travelers seeking a personalized, relaxed pace to soak in two of Italy’s most picturesque towns, guided by a knowledgeable driver and local guide.

What we particularly love about this tour is how seamless and flexible it feels: you get the convenience of door-to-door pickup, the insights of a professional guide, and ample free time to explore each town at your own pace. A potential drawback? The Basilica di San Francesco is closed on Sundays, so if you’re visiting that day, you’ll need to adjust expectations or check alternative options. This tour suits those who value comfort, intimacy, and a deeper connection to Italy’s heritage — perfect for couples, small groups, or solo travelers craving a tailored experience rather than a rushed bus itinerary.

Key Points

• Private and Personalized: Only your group participates, which means more flexibility and tailored attention.
• Comfortable Transportation: Travel in an air-conditioned minivan with a friendly, English-speaking driver.
• Balanced Itinerary: Guided tour of Assisi’s highlights combined with ample free time to explore, plus a scenic stop in Passignano sul Trasimeno.
• Authentic Experiences: Visit UNESCO-listed sites and charming towns, with insights from expert guides.
• Flexible Timing & Easy Booking: Book in advance, with options for pickup from central Florence accommodation.
• Value for Money: Includes transportation, guided visit, and free time, making it an efficient way to see two regions in one day.

An In-Depth Look at the Full Day Private Tour to Assisi and Cortona

This tour offers a well-rounded taste of some of Italy’s most beloved hill towns, perfectly suited for travelers wanting more than just a fleeting glance. Here’s how it all unfolds, with insights into what makes each stop meaningful.

Starting Out: Early Morning Pickup in Florence

Your day kicks off at 9:00 am at Piazza dei Cavalleggeri. From here, a comfortable, air-conditioned minivan whisks you out of the city, setting the tone for a smooth and stress-free day. The driver, usually an English speaker, not only gets you where you need to go but often shares interesting tidbits about the regions you pass through—something we always appreciate.

First Stop: Passignano sul Trasimeno (30 minutes)

Your first quick stop is in Passignano sul Trasimeno, a small village perched on the northern edge of Lake Trasimeno. This charming town, with its cobblestone streets, medieval fortress, and lakeside views, offers a peaceful start to your day. Many reviews praise this stop as a lovely introduction; one traveler loved the relaxed vibe and the chance to stretch legs before heading further. Here, you can take a short walk or snap photos of the vibrant waterfront.

While no entrance fee is involved, this stop provides a chance for some quick sightseeing or a coffee break—ideal for resetting after a long drive. If you’re craving a more in-depth visit, you might consider returning here on your own in the future.

Next: Assisi and the Basilica di San Francesco (1 hour guided tour)

The highlight for most visitors is the Basilica of San Francesco, a UNESCO World Heritage site filled with incredible medieval frescoes by Giotto and Cimabue. The guided tour here, led by a professional guide, offers insights into the art and architecture that make this place so special.

However, note that the basilica is closed on Sundays—a crucial detail for planning. If your tour falls on a Sunday, you’ll explore Assisi’s streets without the basilica visit, which might be a disappointment but still offers plenty to see. The guide enriches your experience with stories about Saint Francis, the town’s history, and the art within the basilica.

Following the guided tour, you’ll enjoy an hour of free time in Assisi itself. This window allows you to wander the winding streets, visit smaller churches like Santa Chiara, or simply relax in a cafe. Reviewers often mention the town’s medieval charm—its stone buildings and peaceful atmosphere—making this a much-cherished moment.

The Final Stop: Cortona (2 hours free time)

After Assisi, the journey continues southward to Cortona, the town made famous by Under the Tuscan Sun. Here, you’ll have two hours of free time to explore at your own pace. Wander the narrow alleys, admire the views over the Val di Chiana, or visit local artisan shops. Many travelers comment on how Cortona’s rustic beauty and historic sites create the perfect backdrop for a relaxed walk.

From reviews, we learn that guides and drivers are friendly and communicative—an important factor when navigating these complex hill towns. One reviewer mentioned that the driver was “ramah san komunikatif” (friendly and communicative), making the experience feel more personal. Visitors love to take photos of the panoramic vistas and enjoy a leisurely lunch or coffee in the piazzas.

Ending the Day

The tour wraps up at the meeting point in Florence, with an estimated return in the late afternoon or early evening. The total duration is approximately 10 hours—an immersive yet manageable day trip, especially considering the convenience and depth of experience.

What Makes This Tour Stand Out?

Transportation: Traveling in an air-conditioned minivan with just your private group means you avoid crowded buses and rigid schedules. It’s a more comfortable way to move between towns, especially if you’re traveling with family or friends.

Guided and Free Time Balance: The combination of a guided tour in Assisi and free time in both towns grants a rich experience—you get expert insights plus the flexibility to explore your own way. One reviewer noted, “Our guide was everything you might want on experiencing this very special place,” highlighting how knowledgeable guides make a difference.

Authentic Cultural Touches: From Passignano sul Trasimeno’s lakeside charm to Cortona’s vibrant arts scene, every stop offers a slice of real Italy away from tourist crowds.

Price and Value: At around $605 per person, this tour is an investment in comfort and depth of experience. When you factor in transportation, guided visits, and free time, it becomes an efficient way to see two regions with no logistical headaches.

Who Would Enjoy This Tour?

This experience is perfect for those who value personalized attention, culture, and comfortable travel. It suits travelers who want to avoid the chaos of large group tours and prefer a flexible, relaxed pace. It’s also great for small groups, couples, or solo travelers eager for a mix of guided and independent exploration.

Final Word: Is This Tour Worth It?

If you’re looking for a day trip that combines scenic beauty, historical sites, and real Italian village life without the hassle of public transport, this tour offers excellent value. The private nature means you can tailor your experience, and the knowledgeable guides ensure you don’t miss the stories behind each site.

The stops in Assisi and Cortona are two of Italy’s most photogenic and culturally significant towns, and this tour makes it easy to enjoy both in one day. The seamless transportation, flexible free time, and personalized service make it a standout option for those wanting a stress-free yet enriching experience.

If you’re keen to indulge in Italy’s art, history, and landscapes at your own pace, this trip hits all the right notes.

FAQ

Is pickup included in the tour?
Yes, pickup from your centrally located Florence accommodation is offered, making it convenient to start your day stress-free.

What is the duration of the tour?
The entire experience lasts about 10 hours, including travel time, guided tours, and free exploration.

Can I visit the Basilica of San Francesco on Sundays?
No, the basilica is always closed on Sundays. If your tour is on a Sunday, you’ll visit Assisi without the basilica interior.

What is included in the price?
Transportation in an air-conditioned minivan, an English-speaking driver, a guided tour of Assisi, and free time in Assisi and Cortona are included. Lunch and entrance fees are not.

Is this tour suitable for families?
Yes, it’s suitable for small groups, couples, or solo travelers. The private nature offers flexibility and comfort.

Are there any additional costs?
Extras like meals, souvenirs, or optional guided tours in Cortona are not included.

What should I wear?
Comfortable shoes for walking are recommended, as both towns have cobbled streets. Remember to cover shoulders and knees when visiting the basilica.

Can I customize my experience?
As a private tour, there’s some flexibility, especially with free time in each town, allowing you to explore more or relax as you wish.

How far in advance should I book?
On average, this tour is booked about 108 days ahead, so early booking is recommended to secure your spot.

What if the weather is bad?
The tour requires good weather; if canceled due to poor conditions, you’ll be offered a different date or a full refund.

In essence, this private day trip from Florence to Assisi and Cortona offers a thoughtfully curated glimpse into Italy’s artistic, spiritual, and scenic treasures. Perfect for travelers seeking comfort, authenticity, and a deeper connection to Italy’s enchanting landscapes and towns.