Private Full-Day Tour of Assisi and Cortona from Florence

Exploring the Private Full-Day Tour of Assisi and Cortona from Florence

Taking a full day to explore Assisi and Cortona from Florence offers an excellent way to see some of Italy’s most iconic towns without the hassle of planning. This private tour, operated by Ciao Florence Tours, promises a seamless, comfortable experience with personalized attention, making it perfect for travelers wanting a mix of religious heritage, medieval charm, and breathtaking landscapes.

What stands out most is the flexibility to explore each town at your own pace—thanks to the generous free-time periods—and the luxury transport in a Wi-Fi-equipped Mercedes. However, some travelers have noted that the price may seem steep for those expecting guided tours in every stop, as entries and meals are not included.

This tour suits those craving a combination of cultural sightseeing and leisure, especially if you want to avoid large group tours and enjoy a more intimate experience with expert drivers taking care of the logistics. Whether you’re a history enthusiast, a lover of scenic drives, or simply want a taste of Tuscany and Umbria’s best, this trip offers real value.

Key Points

• Private, Comfortable Transport: Travel in style with a Mercedes vehicle that features Wi-Fi for a smooth ride.
• Flexibility in Exploration: Get ample free time in both Assisi and Cortona to wander, take photos, and soak in the atmosphere.
• Historical and Cultural Highlights: Visit major religious sites in Assisi and enjoy the medieval charm of Cortona.
• Expert Driver/Guide: Knowledgeable drivers enhance your experience with local insights and personalized service.
• Ideal for Day-Trippers: Perfect for those staying in Florence who want a full, enriching day outside the city.
• Cost Consideration: The tour costs about $630 per person, but includes hotel pickup, drop-off, and private transport, offering good value for a private experience.

The Full Scope of the Experience

This tour kicks off early in the morning, with a hotel pickup in Florence in a sleek Mercedes Benz. For about two hours, you’ll enjoy scenic views of Tuscany and Umbria’s rolling hills—golden fields, patchwork vineyards, and charming farmhouses—making the journey part of the adventure. Your driver, who speaks English, is there to ensure a relaxing trip and often shares stories or suggestions along the way.

Assisi: A Town of Faith and Medieval Charm

The first major stop is Assisi, a town that radiates spirituality and history. Known as the birthplace of St. Francis and St. Clare, Assisi’s narrow cobblestone streets and white buildings set against lush green valleys create an atmosphere that’s almost otherworldly.

One of the most praised aspects, according to reviews, is the knowledgeable guides and drivers who make the history come alive. For instance, one traveler mentioned that their driver, Oswaldo, not only adapted stops to their preferences but also explained everything with warmth and clarity. This flexibility makes a big difference, especially when you want to linger at certain sites.

The Basilica di Santa Chiara is a must-see. Its white and pink striped marble façade from nearby mountains creates a striking appearance outside, and the interior, though more subdued, contains the tomb of Saint Clare. Visitors appreciate its quiet reverence and its significance for women in religious history.

The Basilica di San Francesco is arguably the star of Assisi. Its two-layer design, with frescoes by Cimabue, Pietro Lorenzetti, and Giotto, leaves a lasting impression. Reviewers highlight the vivid frescoes illustrating Saint Francis’ life, and the sense of serenity inside. Some travelers note that the church is extremely sacred, but it’s also a place where you can quietly reflect on the spiritual journey of the saint.

Nearby, the Basilica di Santa Maria degli Angeli features the tiny Porziuncola chapel—where Saint Francis started his Franciscan order. It’s a humble yet powerful site, decorated with Gothic frescoes, and offers a glimpse into the humble beginnings of one of Italy’s most beloved saints.

Lunch and Leisure

After exploring Assisi’s religious sites, the tour offers a lunch break (own expense), giving you the chance to try local dishes, perhaps in a trattoria overlooking the valley. The flexibility here is appreciated, as reviewers often mention that exploring Assisi independently allows you to tailor your experience—whether that’s a quick snack or a leisurely meal.

Cortona: The Film-Famous Hilltop Town

Post-lunch, you’ll head to Cortona, a town made famous by Under the Tuscan Sun. The two-hour stop here is praised for its medieval architecture, stunning views, and art-filled streets. The town’s Etruscan roots make its history particularly fascinating, and many visitors enjoy wandering at their own pace, discovering boutique shops, galleries, and cafes.

One reviewer admired how Placido, the driver, provided great tips, making their experience even richer. Cortona’s stunning vistas over gentle hills are a highlight, and the relaxed atmosphere makes it an excellent place for photos or a quick coffee.

Returning to Florence

By late afternoon, your driver will take you back to Florence, where the tour concludes with a drop-off at your hotel. The 10-hour duration generally means a long but fulfilling day, leaving you with a well-rounded impression of these two iconic towns.

What We Love About This Tour

The personalized touch of a private guide and driver makes all the difference. They don’t just chauffeur you around—they share stories, offer tips, and adapt to your interests, which is evident from reviews praising guides like Oswaldo and Placido.

The scenic drives through Tuscany and Umbria are a highlight, especially if you appreciate picturesque landscapes. The opportunity to explore at leisure in both towns means you can slow down and really soak in the atmosphere, which is often missed in larger group tours.

Religious sites and medieval architecture are deeply woven into the experience, making it ideal for history buffs or spiritual travelers. The frescoes in Assisi are frequently singled out as captivating, and the sense of walking in the footsteps of saints adds a special touch.

Possible Drawbacks

While the tour offers a lot of value, the cost may be steep for some, especially since meals, entrance fees, and souvenirs are not included. For travelers on a tight budget, this could add up quickly. Some reviews also mention the lack of guided tours at each site, so if in-depth historical or artistic commentary is a priority, you might find this tour somewhat limited.

On top of that, the timing means a lot of the day is spent in transit, which can be tiring if you’re not accustomed to long drives. However, the private transport and scenic routes tend to make this a more comfortable experience.

Who Should Consider This Tour?

This private tour best suits travelers who value comfort, flexibility, and personalized attention. If you want a comprehensive yet relaxed day visiting Assisi’s religious landmarks and Cortona’s scenic streets, it’s a strong choice. It’s also ideal for those who prefer to avoid large groups and enjoy more intimate exploration.

Those interested in art, architecture, and history will find this tour particularly rewarding. It’s great for couples, families, or small groups seeking a luxurious day trip without the hassle of navigating on their own.

However, if you’re on a very tight budget or prefer guided tours with detailed narration at each stop, you might want to consider other options. Still, for the value of transportation, flexibility, and the ability to explore independently, this tour hits many sweet spots.

FAQ

Is hotel pickup included?
Yes, the tour features 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 about two hours, allowing you to enjoy the scenic views of Tuscany and Umbria during the trip.

Are entrance fees included?
No, entrance fees are not included, so you’ll need to pay for entry to sites if you choose to visit inside.

Can I explore Assisi and Cortona on my own?
Absolutely, this tour offers free time in both towns for you to stroll, take photos, and enjoy local cafes at your own pace.

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

Is food included in the tour?
No, meals are at your own expense, giving you the freedom to choose local restaurants or cafes.

What should I bring?
Comfortable walking shoes are recommended, especially in Assisi and Cortona’s cobbled streets. Bringing a water bottle and camera is also a good idea.

Is this tour suitable for children?
Yes, as long as your family members are comfortable with a full day of sightseeing and driving, but note that some religious sites might not be suited for very young children.

The Bottom Line

This private full-day tour from Florence offers a well-balanced mix of religious heritage, medieval charm, and scenic beauty. With expert drivers, flexible schedules, and the chance to explore on your terms, it appeals to those who want a personalized, relaxed experience of Assisi and Cortona.

While it’s priced higher than some group options, the comfort, privacy, and convenience make this a worthwhile choice for travelers seeking a more intimate day trip. It works best for those who appreciate self-guided exploration within a structured, scenic framework.

In essence, if you’re craving a luxurious, scenic, and culturally rich day outside Florence, this tour offers a compelling way to see two of Italy’s most beloved towns with ease and style.