Private Full-Day Tour of Assisi and Cortona from Florence

A Day of Sacred Beauty and Tuscan Charm: Private Tour to Assisi and Cortona

If you’re visiting Florence and craving a taste of Italy’s spiritual and scenic treasures, this private full-day tour to Assisi and Cortona offers a compelling mix of history, architecture, and breathtaking views. For $630 per person, you’ll enjoy about 10 hours of personalized exploration, comfortably transported in a luxury Mercedes Benz with Wi-Fi, with hotel pickup and drop-off included.

What we especially love about this experience is the chance to walk in the footsteps of Saint Francis in Assisi, feeling the reverence in the air as you wander through cobblestone streets and visit iconic basilicas. Plus, the time spent in Cortona—a quintessential Tuscan hilltop town—gives you a relaxed, unhurried atmosphere perfect for soaking up the local vibe and taking plenty of photos.

One potential consideration is that lunch and entrance fees are at your own expense, so you’ll want to budget accordingly. Also, with about two hours driving each way, this tour suits those comfortable with a bit of time on the road, but it’s well worth it for the depth of experience. This trip works best for travelers who love history, architecture, art, or simply want a scenic escape from Florence’s city bustle into the quieter charms of Umbria and Tuscany.

Key Points

• Flexible exploration: You get time to wander independently in Assisi and Cortona, allowing personal discovery.
• Comfortable transport: Travel in a private Mercedes with Wi-Fi, making the journey relaxing and scenic.
• Sacred sites and stunning views: Visit major basilicas and walk the streets Saint Francis once called home.
• Authentic Tuscan and Umbrian landscapes: Enjoy the rolling hills, scenic vistas, and medieval architecture.
• Ideal for spiritual seekers and romantics: The towns exude history, charm, and a sense of timeless tranquility.
• Cost and value: While the price is considerable, the private, all-day convenience and in-depth experience justify it for many.

Detailed Review: What This Tour Offers and Why It Matters

Starting in Florence: Comfort and Convenience

The tour begins bright and early at 8:30 am with a hotel pickup in Florence. We loved the way this eliminates the hassle of finding a meeting point, especially after a busy morning or if you’re staying outside the city center. Your driver, a local expert, greets you in a sleek Mercedes Benz, equipped with Wi-Fi—perfect for catching up or sharing photos as you roll through the Tuscan and Umbrian countryside.

The drive itself is a highlight, offering scenic views of rolling hills, vineyards, and olive groves. We found it relaxing to sit back in the plush seats as the driver navigates the sometimes winding roads, giving us glimpses of the landscape that makes this part of Italy so beloved.

Assisi: Walking in Saint Francis’ Footsteps

Arriving in Assisi after about two hours, you’re immediately struck by the town’s white buildings and lush valley views. This hilltop town is more than picturesque; it’s a living testament to Italy’s spiritual tradition. As many reviews note, the atmosphere is palpable, especially during quieter seasons when crowds thin out, as one visitor remarked, “Assisi was beautiful. It was the low season so no crowds and lots of atmosphere.”

You’ll have roughly three hours to explore independently—plenty of time to wander at your own pace. Highlights include:

• Basilica di Santa Chiara: Known for its pink and white striped marble exterior and the tomb of Saint Clare, this church offers a quiet, reverent space that’s both beautiful and historically significant. Inside, you might find the frescoes long lost, but the sense of history remains palpable.

• Basilica di San Francesco: The star of Assisi, this basilica is both an architectural marvel and a treasure trove of artwork. The frescoes by Giotto and others tell the story of Saint Francis’ life in vivid color. The lower church, housing his tomb, offers a sense of being close to the saint himself.

• Basilica di Santa Maria degli Angeli: Slightly outside the town center, this basilica houses the Porziuncola, a tiny chapel where Saint Francis founded the Franciscan order. It’s a humble yet deeply meaningful site that visitors find both peaceful and inspiring.

One guest highlighted that their guide, Oswaldo, “changed stops to accommodate us and explained everything,” which suggests that flexibility is a key advantage of this tour.

Lunch Break: On Your Own but Well-placed

A note from the reviews is that lunch is not included, so you’ll want to budget time and money for an authentic meal. Assisi has charming cafes and trattorias offering everything from fresh pasta to local wines. We recommend taking a moment to enjoy a slice of Terni-style pizza or a simple bruschetta, paired with a glass of local wine or a refreshing mineral water.

Moving to Cortona: A Picture-Perfect Tuscan Town

After your spiritual and cultural walk through Assisi, the journey continues to Cortona, roughly a two-hour drive away. This town became famous worldwide thanks to the film “Under the Tuscan Sun,” and it’s easy to see why. The narrow alleys, medieval buildings, and panoramic views of the Val di Chiana make it a photographer’s paradise.

In Cortona, you’ll have another two hours of free time. Many reviews mention how much travelers appreciate the medieval architecture and the chance to stroll freely, soaking in the timeless charm. Here, you might explore local shops, visit the town’s Etruscan museum, or simply sip a coffee while watching the world go by.

Return to Florence: A Relaxed End to Your Day

By late afternoon or early evening, your driver will collect you for the journey back. The return trip gives you time to process the day’s sights, perhaps replaying the frescoes in your mind or savoring the views from the car window.

The tour concludes with a drop-off at your hotel, making it seamless after a long day of sightseeing.

Why This Tour Works and Who It’s For

This experience offers a balanced mix of sacred art, historic architecture, and scenic landscapes, making it great for travelers who love history, spirituality, or just want to enjoy the peace of Italy’s hill towns. The private format ensures flexibility—reviews indicate that guides often adapt stops based on your interests, which is rare in group tours.

The luxurious transportation and hotel pickup add value, especially for those who prioritize comfort and convenience. It’s also perfect for those who want to avoid the hassle of driving themselves, allowing you to relax and truly enjoy the scenery.

However, the price reflects that level of service, so it’s best suited for travelers who appreciate personalized attention or those eager to maximize their time exploring without the worry of logistics.

Frequently Asked Questions

How long is the drive from Florence to Assisi?
Expect about two hours each way, allowing plenty of time to enjoy the scenery and relax in comfort.

Are entrance fees included?
No, entrance fees to basilicas and sites are at your own expense. The tour is designed for flexible exploration and personal preference.

Can I customize my stops in Assisi and Cortona?
While the tour is private and offers some flexibility, the itinerary is generally fixed. However, guides are often accommodating if you wish to spend more time in certain sites.

Is food included in the tour?
No, meals are not included. You’ll need to budget for lunch, but there are many local options in both towns.

What is the group size?
This is a private tour, so only your group will participate, ensuring a personalized experience.

Is this tour suitable for all ages?
Generally yes, especially for those comfortable with walking and a full day of sightseeing. Accessibility details aren’t specified, so it’s best to consider your personal needs.

Final Thoughts

This private full-day tour from Florence to Assisi and Cortona balances spiritual exploration, artistic discovery, and scenic beauty. It’s particularly suited for travelers who value flexibility, comfort, and authentic Italian towns rather than crowded group experiences. The opportunity to independently explore the basilicas and towns at your own pace adds a layer of intimacy and personalization that many travelers find rewarding.

While the cost may seem high, the convenience of private transport, the opportunity to see two iconic towns efficiently, and the chance to walk in Saint Francis’ footsteps make it a worthwhile investment for those eager to deepen their Italian experience beyond Florence.

If you enjoy a blend of history, art, and breathtaking views, and prefer traveling in style with minimal hassle, this trip offers a memorable way to connect with Italy’s spiritual and scenic heritage. It’s a journey that many find both inspiring and restorative—an authentic taste of Tuscany and Umbria in a single day.