Private Full-Day Tour of Assisi and Cortona from Florence

Exploring Assisi and Cortona in a Day: A Balanced Look at This Private Tour

If you’re after an immersive day exploring two of Italy’s most picturesque towns—Assisi with its spiritual aura and Cortona with its charming, film-famous streets—this private full-day tour from Florence offers a lot. With the promise of comfortable Mercedes transportation, hotel pickup, and personalized free time, it sounds like an ideal way to squeeze a taste of Umbria and Tuscany into one memorable trip.

What we particularly like is the flexibility the tour offers—you’re not stuck with a rigid schedule, so you can wander at your own pace and really soak in the atmosphere of each place. However, a potential consideration is the cost—at around $630 per person, it’s an investment, but for those who value convenience, comfort, and a curated experience, it could be well worth it. This tour seems best suited for travelers who appreciate historical religious sites, stunning scenery, and small-town charm, and who don’t mind a long day on the road.

Key Points

• Comfortable private transport with Wi-Fi ensures a relaxed ride through scenic landscapes
• Flexible free time in Assisi and Cortona allows for personalized exploration
• Guided insights enhance understanding of religious and historical significance
• Beautiful scenery of Tuscany and Umbria set the perfect backdrop for your day
• Focus on authenticity and value—you get privacy, convenience, and access to important sites
• Consideration needed for extra expenses like food, entrance fees, and optional guide services

An In-Depth Look at the Tour Experience

Starting Point: Comfortable Pickup in Florence

The day kicks off with a hotel pickup in Florence, which is ideal for minimizing the hassle of finding meeting points. You’ll be chauffeured in a luxury Mercedes Benz with Wi-Fi—a small but significant perk that makes the journey more enjoyable, allowing you to relax or catch up on travel planning. This setup is perfect for travelers who prefer a private, intimate transfer rather than a crowded bus or group.

The Scenic Drive into Umbria and Tuscany

As your driver navigates the rolling hills, we loved the view of the Tuscan and Umbrian countryside—a patchwork of vineyards, olive groves, and quaint villages. The roughly two-hour drive to Assisi offers ample opportunity to appreciate Italy’s natural beauty from the comfort of your seat. The driver, often described as knowledgeable and friendly, can sometimes customize the stops, as one reviewer mentioned, adding a personalized touch that enhances the experience.

Exploring Assisi: A Sacred Hilltop Town

Assisi is an absolute highlight. Known as the birthplace of St. Francis and St. Clare, it’s a place that exudes spiritual calm and medieval charm. With around three hours to explore, you’ll have the chance to walk through narrow cobblestone streets that echo the footsteps of Saint Francis himself, which many visitors find moving.

The key religious sites are:

• Basilica di Santa Chiara: This church dedicated to Saint Clare features colorful striped marble outside and a simple interior that pays homage to her humble, faith-driven life. Inside, you’ll find her tomb, making it a pilgrimage spot for many. Reviewers appreciated that the basilica’s exterior’s striking color contrasts with its interior’s simplicity, which adds to its profound atmosphere.

• Basilica di San Francesco: Built over Saint Francis’s tomb, this church is a masterpiece. The frescoes by Giotto are a feast for the eyes—vivid and full of life, they tell stories of Saint Francis’s life. Visitors have praised the upper church’s light-filled, heavenly ambiance and the frescoes’ vivid storytelling, which help bring the saint’s legacy to life.

• Basilica di Santa Maria degli Angeli e dei Martiri: Located just outside the town center, this basilica is home to the Porziuncola, a tiny chapel where Saint Francis began his work. The frescoed interior and its historical significance make it a meaningful stop, especially for those interested in religious history.

One reviewer shared that they appreciated the chance to explore Assisi’s narrow streets without the usual crowds during the low season, adding to the town’s atmospheric charm. The free time is generous enough for a relaxed visit, and you can choose to peek into shops, enjoy local cafés, or simply soak up the spiritual and artistic aura.

Lunch Break: On Your Own

The tour mentions a break for lunch, which is at your own expense. Given the town’s charm, this is a perfect opportunity to try some local specialties—perhaps a plate of pasta or a casual panino—while enjoying the view. Many travelers find that exploring Assisi’s cuisine adds a delicious layer to the experience, though it’s wise to budget extra time and money for this.

Moving on to Cortona: The Tuscan Dream

After a meaningful morning in Assisi, your driver will take you to Cortona, roughly a two-hour scenic drive. This town gained fame as the filming location of Under the Tuscan Sun, and it’s easy to see why. The elevated streets, medieval architecture, and views of the surrounding hills create a picture-perfect setting.

In Cortona, you’ll have approximately two hours of independent exploration. The town’s Etruscan roots are visible everywhere—from ancient walls to archaeological finds—making it a fascinating spot for history buffs. The charming streets are filled with flower-filled balconies, artisan shops, and cozy cafés, perfect for photos and leisurely strolls.

Reviewers often mention enjoying the freedom to explore at their own pace—whether that’s popping into a gallery, grabbing an espresso, or simply wandering the scenic alleyways. One reviewer noted that Cortona’s medieval charm is even more striking without the crowds of high season, allowing for a more authentic, quiet experience.

Return Journey: Comfort and Convenience

As the day winds down, you’ll rejoin your driver for the journey back to Florence. The early evening drop-off ensures you avoid feeling rushed, and the ride offers a great chance to reflect on the day’s highlights. The entire experience is designed to prioritize comfort and flexibility, making it suitable for those who prefer a personalized, leisurely approach to sightseeing.

What Makes This Tour Stand Out?

The private nature of the tour is one of its strongest points. Unlike bus-based excursions, you gain the flexibility to linger where you want or skip certain stops if you prefer. Travelers noted that guides—like Oswaldo or Placido—are friendly, accommodating, and knowledgeable, often adding insightful commentary that enriches each visit.

The licensed transportation, with Wi-Fi and bottled water included, elevates the overall comfort. The scenic drives through Tuscany and Umbria are more than just transportation—they’re part of the experience, offering stunning views that many visitors treasure.

Price and Value

At approximately $630 per person, this tour isn’t cheap. But when you consider the all-day private transportation, hotel pickup and drop-off, and the personalized itinerary, it offers good value. The convenience of avoiding public transport or multiple bookings, coupled with the expert insight and flexibility, appeals to travelers who prioritize comfort and authenticity.

Who is This Tour Best For?

This experience is ideal for those who value personalized service, are interested in religious and historic sites, and want to enjoy the scenic beauty of Italy without the hassle of navigating on their own. It suits travelers who don’t mind a full day of sightseeing and are happy to pay for the added comfort and convenience. If you’re traveling with family, friends, or a small group, the private aspect makes it even more appealing.

The Sum Up

This private full-day tour of Assisi and Cortona offers a well-rounded blend of spiritual sites, medieval charm, and scenic landscapes. You’ll love the convenience of private transport, the freedom to explore at your own pace, and the opportunity to enjoy Italy’s beautiful countryside along the way. The stops in Assisi are deeply meaningful, especially if you’re interested in Saint Francis’s life, while Cortona provides that quintessential Tuscan village experience.

While the price might seem high, the value lies in the comfort, flexibility, and authentic insights you gain—especially with guides praised for their friendliness and knowledge. It’s a perfect choice for travelers eager to combine culture, history, and natural beauty without sacrificing ease.

If you’re after a personally tailored, relaxed way to see two of Italy’s most charming towns, this tour delivers on those promises. Just remember to budget for meals, entrance fees, and perhaps some souvenirs—because you’ll want to remember this day for a long time.

FAQ

Is hotel pickup and drop-off included?
Yes, the tour includes convenient hotel pickup and drop-off in Florence, making the start and end of your day hassle-free.

How long is the drive from Florence to Assisi?
The drive takes approximately two hours, offering scenic views of the Tuscan and Umbrian countryside.

What sites can I visit in Assisi?
You can explore the Basilica di Santa Chiara, Basilica di San Francesco, and Basilica di Santa Maria degli Angeli, all rich with religious and artistic significance.

Can I customize the stops or duration?
As a private tour, you have some flexibility to adjust the stops or time spent in each location, depending on your interests.

Is lunch included?
No, lunch is at your own expense, giving you the freedom to choose where and what to eat in Assisi.

What should I bring?
Comfortable shoes for walking cobblestone streets, some cash or cards for entrance fees, meals, and souvenirs, and a camera for capturing the stunning views.

Are entrance fees included?
No, entrance fees are not included; you’ll need to pay for individual site tickets if you wish to enter certain buildings.

Who is this tour best suited for?
Travelers who appreciate comfort, personalized attention, and the freedom to explore at their own pace, especially those interested in religious, historical, and scenic sites.

This tour combines the best of Italy’s spiritual history and rustic landscapes with all the perks of private transportation, making it an excellent choice for those wanting a memorable, stress-free day trip from Florence.