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Discover Tuscany’s hidden gems with this private tour from Florence to Cortona and Arezzo, featuring stunning views, film locations, and personalized attention.
A Practical Look at the Florence to Cortona and Arezzo Private Tour
This private day trip from Florence takes you beyond the busy city streets to explore two lesser-visited, yet incredibly charming Tuscan towns—Cortona and Arezzo. For around 9 hours, you’ll enjoy a comfortable, all-inclusive experience that includes private transportation, free time to explore, and visits to sites that often escape the average tourist’s itinerary.
What we really appreciate about this tour is how it offers a personalized touch. The private vehicle means fewer crowds and more flexibility. Plus, the chance to visit filming locations from movies like Under the Tuscan Sun and Life is Beautiful adds a fun, pop-culture flavor to the day. On the flip side, it’s worth noting that this experience doesn’t include a guide, only a knowledgeable driver, which might matter if you’re looking for detailed historical commentary. This tour suits travelers who want to see authentic towns at their own pace, with a focus on comfort and convenience.

For a more personal experience, these private Florence tours deliver individual attention
Your adventure begins bright and early at 8:30am, with hotel pickup included. This punctual start ensures you maximize your time in Tuscany without feeling rushed. The round-trip private transportation is a major highlight—think of it as your scenic, stress-free ride through the rolling hills, rather than a crowded bus. The private vehicle comfortably accommodates your group, offering a more intimate experience.
After a roughly two-hour drive from Florence, your first stop is Piazza Grande in Arezzo. This historic square is a visual feast, with medieval architecture framing lovely views of the Tuscan landscape. The square is largely free to wander, giving you a chance to appreciate its timeless charm without the crowds. The reviews mention the “stunning views,” and you’ll see why — from the square, you get a fantastic vantage point overlooking the countryside.
While there’s no admission fee, the focus here is on soaking in the ambiance, photos, and a sense of authentic Tuscan life. You might find local cafes starting to stir, and the atmosphere is relaxed, perfect for some quiet reflection or snapping pictures.
Next, it’s about a two-hour visit to Cortona, a town made famous by Under the Tuscan Sun. The highlight here is the Duomo di Cortona, a church that’s worth a quick look for its architecture and the film connection. You’ll spend time wandering its surroundings, taking in the panoramic vistas, and perhaps reminiscing about the movie scenes shot here.
The guide’s insights enrich the experience, especially if you’re a film buff, as the filming locations for Life is Beautiful are also nearby in Arezzo. The reviews mention that the guide Massimo made the trip special, providing details and stories that bring the towns’ history and film ties to life. Interestingly, some travelers have noted the driver’s role is not that of a traditional guide, meaning the focus is on transportation and logistical support, but a knowledgeable driver can still enhance the day with local tidbits.
Both towns offer generous free time – roughly two hours in each. This is your window to explore independently, browse shops, enjoy a coffee, or simply sit back and take in the scenery. This flexible approach is a real plus for travelers who prefer to set their own pace rather than follow a fixed tour schedule.
Given the tour’s price point ($377.47 per person), a significant value is the comfort and convenience it offers. No need to worry about parking, navigating unfamiliar streets, or rushing from site to site. Plus, since it’s a private experience, your group can tailor how long you spend at each location and what you prioritize—be it photos, snacks, or just relaxing.
One point worth noting is that the tour does not include a professional guide for site visits—only a driver. Some reviews highlight this; while the driver is knowledgeable, they aren’t licensed guides equipped to lead museum or site tours. If you’re looking for in-depth historical commentary or guided museum visits, you may want to arrange for an additional guide.
Also, lunch is not included, so you should plan to bring snacks or budget time for a meal during your free periods. The physical aspect of the tour is manageable for most, but good walking shoes are advised, especially as both towns involve some uneven streets and uphill paths.
For travelers craving an authentic, relaxed exploration of Tuscany’s smaller towns, this day trip offers a perfect balance of comfort, culture, and scenic beauty. The private transportation and flexible timing make it easy to enjoy each location at your own pace. Plus, the inclusion of film locations adds a playful touch that appeals to movie lovers.
If you’re interested in stunning panoramic views and historic architecture without the large crowds, this tour delivers. The knowledgeable driver, who often doubles as an informal storyteller, helps you get a taste of Tuscany’s true character.
However, if you’re eager for in-depth guided tours or want to explore museums with a licensed guide, you might find this setup somewhat limited. Also, those seeking a culinary experience or a more structured itinerary might prefer other options.

This private tour is ideal for couples, small groups of friends, or solo travelers who want a personalized, comfortable day exploring Tuscany’s lesser-known towns. It suits those who value flexibility over rigid schedules and prefer a relaxed pace to truly soak in the atmosphere. Film buffs will enjoy the added layer of visiting locations from Under the Tuscan Sun and Life is Beautiful.
Travelers who appreciate stunning views and authentic town atmospheres, without the hassle of driving or parking, will find this experience both enjoyable and convenient. Keep in mind, it’s best suited for those with moderate physical fitness and comfortable shoes, as both towns involve walking on uneven streets.
In summary, this tour strikes a careful balance between ease, authenticity, and cultural charm. It’s a wonderful way to escape the crowds, enjoy beautiful scenery, and uncover some of Tuscany’s secret treasures.

Does this tour include a guide?
No, it features an English-speaking driver who provides transportation and some commentary, but it does not include a licensed guide for site tours.
Is lunch included?
No, lunch is not included. You should plan to bring snacks or enjoy meals during your free time in the towns.
How long are the stops?
Each town stop is approximately two hours, offering enough time to explore independently, take photos, and soak in the atmosphere.
Is this tour suitable for all fitness levels?
Yes, but travelers should have moderate physical fitness and be prepared for walking on uneven streets and some uphill paths.
What is the price and what does it include?
At $377.47 per person, the tour includes private transportation, hotel pickup and drop-off, and visits to both towns.
Can I cancel if my plans change?
Yes, free cancellation is available up to 24 hours in advance, allowing flexibility to adapt to your plans.
To sum it up, if you’re looking for a personalized, scenic, and stress-free way to discover two of Tuscany’s charming towns, this private tour offers a wonderful experience. It’s perfect for those seeking authentic towns, beautiful views, and the flexibility to explore at their own pace, all while avoiding the crowds. Just remember, if you want detailed guided commentary or a culinary focus, you might want to look elsewhere or add on a guide. For most travelers, this day trip strikes a lovely balance between comfort and discovery.