Full Day Private Guided Tour to Assisi and Cortona from Florence

This full-day private tour from Florence takes you to two of Italy’s most enchanting towns: Assisi and Cortona. For $605.01 per person, you’ll spend about 10 hours exploring with a dedicated driver and guide, avoiding the hassle of public transport. The experience includes visits to the Basilica di San Francesco in Assisi, famous for its stunning frescoes, plus ample free time to stroll through Assisi’s medieval streets. Afterward, you’ll head to Cortona, the Tuscan hill town made famous by “Under the Tuscan Sun,” for two hours of exploration and relaxation.

What we really appreciate about this tour is its personalized nature—it’s a private experience, so your group can set a relaxed pace. The drive itself is comfortable, thanks to an air-conditioned minivan. Plus, the combination of guided highlights and free time allows for both in-depth understanding and spontaneous discovery.

A possible consideration is the long travel time involved—roughly 10 hours—so this tour suits those comfortable with a full day on the road. Also, the visit to the Basilica of San Francesco is not available on Sundays, so plan your trip accordingly.

This tour is perfect for travelers who want a flexible, intimate experience with expert insights without the constraints of a large group. If you’re interested in art, historic towns, and authentic Italian scenery, you’ll find plenty to love here.

Key Points

• Private, personalized experience ensures flexibility and intimacy
• Two beautiful towns—Assisi and Cortona—each with unique charm and history
• Guided tour of Assisi’s Basilica with masterpieces by Giotto and Cimabue
• Ample free time to explore and absorb the atmosphere in each town
• Comfortable transportation in an air-conditioned minivan
• Ideal for those seeking hassle-free, immersive day trips from Florence

Discovering the Best of Assisi and Cortona in One Day

When booking a day trip from Florence that combines history, art, and stunning scenery, this private tour hits many high points. For around $600, you’re paying for a full day of guided exploration, with the freedom to wander at your own pace. It’s more personalized than a big group tour, and the experience is tailored to your group’s interests and timing.

The Itinerary: A Closer Look

Stop 1: Passignano sul Trasimeno
The journey begins with a quick 30-minute stop at Passignano sul Trasimeno, a charming lakeside village in Umbria. This is a perfect spot to stretch your legs, enjoy scenic views of Lake Trasimeno, and soak in the tranquil vibe of narrow cobblestone streets and waterfront cafes. You might find this a lovely introduction to Italy’s less touristy, authentic lakeside life. The stop is free, making it a great way to ease into the day.

Stop 2: Basilica di San Francesco in Assisi
Next, the highlight for many is the visit to the Basilica of Saint Francis, a UNESCO World Heritage site. Built in the 13th century to honor the saint, this complex features two basilicas—lower and upper—decorated with frescoes by Giotto, Cimabue, and other masters of medieval art. These artworks aren’t just beautiful—they’re profound, illustrating Saint Francis’s life and teachings in vivid colors.

Given the basilica’s importance, it’s a spiritual and artistic treasure. The guided tour (about an hour) enriches your visit, highlighting the stories behind the frescoes and the architecture. Keep in mind, the basilica is closed on Sundays, so plan accordingly.

Stop 3: Free Time in Assisi
After the guided tour, you get an hour to explore Assisi on your own. We loved how this gives a chance to wander the medieval streets, perhaps visiting other churches or just relaxing in the town square. Assisi’s atmosphere, with its ancient stone buildings and peaceful vibe, makes for a memorable stroll.

Stop 4: Cortona
The final main stop is Cortona, with a full two hours of free time. Famous for its panoramic views over the Val di Chiana and its Etruscan roots, Cortona is a picture-perfect hill town. Its narrow streets, historic churches, and lively cafes make it a favorite among travelers who want authentic Tuscany without the crowds of more popular spots.

We enjoyed the views from Cortona’s walls and the chance to soak up the vibe of a town that inspired the book “Under the Tuscan Sun.” The two hours are enough for a relaxed lunch, some shopping, or just soaking in the scenery.

Transportation and Comfort

Traveling in a modern, air-conditioned minivan makes the long drive more bearable. Your driver, who speaks English, provides commentary along the way, making the journey part of the experience. The private nature of the tour means no worries about fitting into a crowded bus or being rushed through sites.

Authenticity and Value

Many reviews praise the knowledgeable guides and friendly drivers—Giacomo, in particular, was highlighted for his insight and kindness. The flexibility of having both guided and free time allows you to tailor the visit to your interests.

The price of about $600 might seem steep for some, but when you consider the private transport, guided tour, and personalized experience, it offers value—especially when compared to the cost and hassle of arranging independent visits.

Considerations

The main thing to keep in mind is the full-day commitment—it’s a long trip, but one that’s manageable if you’re prepared for a busy day. Also, note that visiting the basilica is not an option on Sundays, which might influence your planning.

This tour is best suited for those who appreciate art, history, and scenic towns, and who prefer a more intimate experience over large group tours. It’s perfect for travelers who want to see two iconic towns comfortably and with expert guidance.

Who Will Enjoy This Tour?

This tour is ideal for history buffs, art lovers, and those seeking a relaxed, personalized day out. If you value guided insight combined with free time to explore, you’ll find it rewarding. It’s also a good choice for travelers who want a hassle-free experience—the private transport and hotel pickup are significant perks.

Couples, small groups, or families will appreciate the personalized touch, avoiding the chaos of larger tours. If you’re interested in authentic Italian towns, stunning frescoes, and scenic vistas, this trip checks all those boxes.

Frequently Asked Questions

Is this tour suitable for all ages?
Yes, most travelers can participate, but keep in mind the full-day length and walking involved in towns like Assisi and Cortona.

Does the tour include lunch?
No, lunch is not included. You’ll have free time in Cortona to choose a restaurant or enjoy a quick snack.

Can I cancel or reschedule?
Yes, the tour offers free cancellation up to 24 hours in advance. Changes less than 24 hours before the start are not accepted.

Is pickup available from my Florence hotel?
Pickup is offered if your accommodation is centrally located in Florence, making it convenient to start your day.

What should I wear or bring?
Comfortable shoes are recommended for walking. Remember, visiting the basilica requires shoulders and knees to be covered, so dress accordingly.

Will I have a guide throughout the visit?
Yes, a professional guide will accompany you for the Assisi visit, providing insights and context.

How long is the drive between stops?
Travel time by minivan is included in the overall 10-hour duration; expect some time on the road but with scenic views and commentary.

Is the basilica always closed on Sundays?
Yes, the Basilica of San Francesco in Assisi is always closed on Sundays, so plan your visit accordingly.

What are the main highlights I should expect?
The frescoes in the basilica, the medieval charm of Assisi, panoramic views from Cortona, and the personalized service that makes this trip stand out.

To sum it up, this private tour offers a wonderful way to experience two of Italy’s most beloved towns with ease and comfort. It’s perfect for those who want a tailored, authentic day with expert guidance, scenic stops, and the freedom to explore. While it requires a full day’s commitment, the combination of art, history, and beautiful scenery makes it well worth the effort. Whether you’re a first-timer to Italy or a seasoned traveler, this trip promises memorable moments in the company of friendly guides and breathtaking views.