Full Day Private Guided Tour to Assisi and Cortona from Florence

Exploring Assisi and Cortona on a Private Day Trip from Florence

If you’ve ever dreamed of experiencing Italy beyond Florence’s legendary art and architecture, a day trip to Assisi and Cortona offers a wonderful escape. This private tour promises a seamless journey, allowing you to explore two of Italy’s most captivating hilltop towns without the hassle of navigating on your own. While I haven’t taken this exact tour myself, reviews and detailed itineraries give us plenty to consider—and it looks like a real winner for those who love history, scenic views, and a touch of local charm.

What really stands out about this experience is the personalized nature of the trip—no big tour groups, just your private group, your driver, and the flexibility to enjoy each stop at your own pace. Plus, the inclusion of guided visits and free time strikes a great balance, giving you insight into Assisi’s spiritual sites and ample opportunity to wander Cortona’s charming streets. However, one thing to keep in mind is that the Basilica of San Francesco in Assisi is closed on Sundays, so plan accordingly if that’s a must-see for you. This tour seems well-suited for travelers craving a more intimate, flexible day away from Florence’s crowds.

<h3 id="section-0">Key Points

• Private and personalized experience with your own group and driver
• Guided tour of Assisi’s Basilica with a professional guide, plus free time to explore
• Additional free time in Cortona for soaking in local atmosphere and views
• Comfortable transportation in an air-conditioned minivan
• Ideal for those wanting a relaxed, flexible day with a mix of guided insight and free exploration
• Consideration: The Basilica in Assisi is closed on Sundays, so plan accordingly

A Detailed Look at the Tour Experience

The Journey Begins at Florence

Your day kicks off early, with a pickup from your Florence hotel or a designated meeting point at Piazza dei Cavalleggeri. The private nature of the tour means you won’t be stuck with strangers, and the air-conditioned minivan promises a comfortable ride. Traveling in a small group or private setting is a huge plus—especially if you prefer a more relaxed and personalized day.

First Stop: Passignano sul Trasimeno

Less than an hour into the drive, you’ll make a brief stop at Passignano sul Trasimeno, a picturesque lakeside town on the northern edge of Lake Trasimeno. It’s a quick 30-minute visit, but enough to enjoy some breathtaking views of the lake and peek into a charming village with medieval roots. The town features cobbled streets, a fortress overlooking the water, and waterfront restaurants. It’s a nice way to stretch your legs and get a sense of the local vibe before heading inland.

Many travelers appreciate this stop as a scenic preview of the day’s later towns. Since it’s a free stop, you can take your time grabbing a coffee or snapping photos without feeling rushed. It sets a relaxed tone for the day.

Assisi: The Heart of the Trip

Next, the focus shifts to Assisi, home of Saint Francis and one of Italy’s most revered pilgrimage sites. The highlight here is a guided tour of the Basilica di San Francesco, which is truly a treasure trove of medieval art, including works by Giotto and Cimabue. But note—it’s closed on Sundays, so if your trip falls on that day, the itinerary might shift slightly.

The guided 1-hour tour is a major value, offering insights into the history and artistry of this UNESCO World Heritage site. You’ll get a glimpse of both the Lower and Upper Basilicas, with their stunning frescoes and spiritual ambiance. After the guided visit, you’ll have about an hour of free time to wander Assisi’s narrow streets, browse local shops, or just soak in the peaceful atmosphere. Many reviews mention how special it is to have this time on your own, away from the crowds.

The Charm of Cortona

After exploring Assisi, the tour heads south to Cortona, a town made famous by Frances Mayes’ book Under the Tuscan Sun. With two hours of free time, you’ll have plenty of opportunity to stroll through cobblestone streets, admire historic churches, and enjoy panoramic views over the Val di Chiana.

Cortona’s appeal lies in its rustic beauty and timeless charm. It’s the kind of place where you can sit at a cafe, watch local life unfold, and marvel at the countryside stretching beyond the town walls. This stop is ideal for those who love wandering and soaking in the atmosphere without a strict schedule.

Wrapping Up the Day

After Cortona, your driver will return you to Florence, ending the tour at the starting point. The entire experience lasts around 10 hours, making it a full but manageable day that combines guided insights with ample free exploration.

What Travelers Love (And What They Mentioned Less Favorable)

Reviewers consistently praise the knowledgeable guides and the personalized touch of the private tour. One reviewer described their guide as “everything you might want on experiencing this very special place,” emphasizing how guided insights enhanced their visit. Another highlighted how their guide made them feel like family, adding warmth and extra effort to the day.

The scenic stops at Passignano sul Trasimeno and Cortona are repeatedly mentioned as highlights. The views, charming streets, and historic architecture seem to deliver exactly what travelers expect from an Italy hilltop town tour. The inclusion of free time is also welcomed, as it allows visitors to explore at their own pace.

Many customers have expressed satisfaction with the driver’s friendliness and communication, making the entire day feel smooth and enjoyable. The air-conditioned minivan and door-to-door pickup add to the comfort and convenience, especially in the heat of summer.

However, a few travelers noted that visiting the Basilica of San Francesco on Sundays is impossible due to closures, which might be disappointing if that was a major part of their plan. It’s a good idea to double-check the schedule and plan accordingly.

The Impact of Price and Value

At around $605 per person, this tour isn’t exactly cheap, but considering the private nature, guided tours, transportation, and flexible schedule**, it’s fair value for those who want an intimate experience without the hassle of navigating alone. The cost covers transportation, the guide, and entry for the Basilica, though lunch and extras aren’t included.

For travelers who appreciate comfort, flexibility, and personalized insights, the price is justified. It’s especially appealing if you prefer not to join large groups or self-drive through unfamiliar regions. The detailed attention from your driver and guide can deepen your understanding and enjoyment of Assisi and Cortona, making it a worthwhile investment.

Who Should Consider This Tour?

This experience is best suited for travelers who value comfort and flexibility and want to avoid the complexities of public transport. It’s ideal for those interested in art, history, and scenic towns without the rush of group tours. It’s also good for visitors wanting to customize their time in each location—whether they prefer guided insight or solo wandering.

If you’re traveling with family or friends who appreciate a more private, relaxed day, this is a great pick. However, if you’re on a tight budget, or if visiting the Basilica on a Sunday is unavoidable, you might want to explore other options or plan accordingly.

FAQs

Is this tour suitable for those who want to visit the Basilica di San Francesco?
Yes, the tour includes a guided visit to the Basilica. However, keep in mind it’s closed on Sundays, so check your schedule and plan accordingly.

How much free time do I get in Assisi and Cortona?
You’ll have about 1 hour in Assisi for wandering after the guided tour, and 2 hours in Cortona for exploring on your own.

Is transportation comfortable?
Absolutely. The tour uses an air-conditioned minivan, making the long drive more comfortable, especially in warmer months.

What’s included in the price?
Your fee covers the private driver, guided tour of Assisi, the stops, and transportation. Lunch, souvenirs, and extras are not included.

Can I cancel this tour?
Yes, you can cancel free of charge up to 24 hours before the scheduled start, for a full refund.

Would this tour be good for families or travelers with children?
While the tour isn’t specifically designed for families, the pace and private setting make it manageable. Just be aware of the walking involved and the need to respect the basilica’s dress code.

In essence, this private day trip offers a well-rounded way to see Assisi and Cortona comfortably and at your own pace. It combines guided art and historical insights with free time for personal discovery, making it ideal for those seeking a meaningful yet relaxed escape from Florence. If you’re after a smooth, personalized experience with beautiful scenery and cultural stops, this tour could be just what you need for a memorable day out.