PRIVATE TRANSFER: from Assisi to Florence with stops in Cortona & Montepulciano

Traveling from Assisi to Florence doesn’t have to be just a straightforward ride. This private transfer experience, with scenic stops in Cortona and Montepulciano, offers a taste of Tuscany’s beauty, history, and flavors all in one day. While it’s not a tour in the traditional sense, it’s an excellent way to see some of the region’s highlights without the hassle of planning transport or worrying about navigation.

What we really like about this experience is how it combines comfortable private transportation with meaningful stops that give you a chance to explore towns famous for their art, history, and wine. Plus, the inclusion of wine tastings and local recommendations makes it feel like a personalized journey rather than a rushed group tour. That said, it’s important to note that this is a full-day drive, so if you’re looking for a more leisurely exploration of each town, or if you’re not keen on long drives, this might not be your best fit.

One thing to keep in mind is that this experience is best suited for those who want a quick, yet enriching peek into Tuscany’s countryside. It’s especially good if you’re short on time but want to squeeze in a few highlights en route to Florence. If you’re looking for more extensive sightseeing or guided tours inside each town, you might want to supplement this with additional activities.

This private transfer with stops offers a practical way to enjoy stunning views, authentic wine experiences, and charming towns, making it a solid choice for travelers who prefer flexibility and comfort over a rigid schedule.

Key Points

• Comfortable private transportation means you avoid crowded buses and can enjoy a relaxed day.
• Stops in Cortona and Montepulciano offer authentic Tuscan charm and stunning scenery.
• Wine tastings in Montepulciano provide a taste of renowned local wines, including Vino Nobile di Montepulciano DOCG.
• The flexibility of a private driver allows for personalized recommendations and stops.
• The duration of about 8 hours makes for a full, yet manageable day trip.
• Cost per person is $290.36, which is quite reasonable considering the private nature and included tastings.

Why Choose This Private Transfer?

This experience is perfect if you want to combine scenic drives with some hands-on local experiences without the structure of a typical guided tour. Since it’s a private activity, your group can enjoy a more intimate and flexible outing. The driver acts as both chauffeur and local guide, offering insights about the areas you pass through and helping you make the most of each stop.

The journey begins with a pick-up at your accommodation in Assisi, which means no worries about public transport or meeting points. As you cruise through the rolling hills of Umbria and Tuscany, you’ll get a glimpse of the landscape that makes this region so beloved. Passing near Lake Trasimeno adds a touch of natural beauty, with the option to request a stop if you’d like to snap some photos or stretch your legs.

Exploring Cortona

Your first stop is Cortona, a town that radiates charm and history. Famous for its roots as an Etruscan settlement, Cortona still bears traces of its ancient origins, which you can imagine as you walk the narrow cobblestone streets. The town’s panoramic views are a highlight, with vistas over the valley and Lake Trasimeno that make for perfect photo ops.

We adore how this stop allows for a free visit, giving you freedom to wander at your own pace. You can explore the medieval architecture, quaint piazzas, and local artisan shops. The visit to Le Celle, the Hermitage of San Francesco outside the city, adds a peaceful, scenic spot to see. Because of its connection to the film Under the Tuscan Sun, Cortona also has a romantic, cinematic feel that many travelers love.

From the reviews, we see that visitors appreciated the knowledgeable local guide and the stunning views. One reviewer mentioned, “We had a very nice private drive from Assisi to Florence with stops in Cortona and Montepulciano that included a wine tasting in Montepulciano. Thanks!” This suggests the town’s beauty is complemented by the personal touch of the driver and the overall relaxed pace.

The Charm of Montepulciano

After Cortona, you’ll head to Montepulciano, a hilltop town famed for its medieval and Renaissance architecture. Here, the highlight is the wine tasting in historic cellars, where a qualified winemaker guides you through the process and explains what makes Vino Nobile di Montepulciano DOCG unique.

You’ll see massive oak barrels that have stored the region’s renowned wines for decades, an experience that wine lovers especially enjoy. The wine tastings are not just about the drinks but about understanding the craftsmanship behind the labels. You get to sample some of the best wines while soaking in the atmospheric underground cellars.

Beyond the wine, Montepulciano offers excellent opportunities to stroll through charming streets, admire the fortified walls, and enjoy local specialties like pork, cheese, and honey. The town’s vibrant history and well-preserved architecture make it a favorite for those wanting a classic Tuscan experience.

From the review, one traveler shared, “During the wine tasting, a qualified winemaker explained the basic characteristics, and the experience of seeing those enormous barrels was incredible.”

Practical Aspects and Value

The entire day is about 8 hours — enough to see these two towns and enjoy some scenic and culinary delights without feeling rushed. The price of $290.36 per person is quite fair, considering you get private transportation, two wine tastings, and personalized recommendations. The cost reflects the convenience and exclusivity, especially since it’s just your group on board.

The vehicle is air-conditioned, which makes the long drive comfortable, especially in the warmer months. Bottled water is also provided to keep you refreshed during the day.

While lunch isn’t included, your driver is happy to point out some excellent local spots for a traditional Tuscan meal. This flexibility allows you to choose a place that suits your taste and budget, whether you want a quick panini or a leisurely sit-down meal.

Downsides and Considerations

Since this is a private transfer, it’s not a guided tour in the traditional sense. If you prefer someone narrating history or guiding you through each site, you might find this format a bit limiting. Also, at about 8 hours, it’s a fairly full day, so if you’re not used to long drives or want to explore each town more extensively, it could feel a bit rushed.

Plus, the tour’s success depends heavily on the driver’s knowledge and attitude. From the reviews, we see that local guides and drivers are generally well-regarded, but it’s worth confirming your driver’s experience if possible.

Who Is It Best For?

This experience suits travelers who enjoy scenic drives combined with cultural and culinary stops. It’s ideal for those who value comfort and flexibility over a rigid schedule and don’t mind a full day on the road. It also works well if you’re eager to sample Tuscan wines and see two of the region’s most charming towns without the hassle of planning your own transport or multiple bookings.

If you’re traveling with a small group or a partner, the private aspect makes it feel more personalized and intimate. It’s also a great way to get a quick overview of this part of Italy if your time is limited but you want a meaningful experience.

Frequently Asked Questions

Is this a guided tour inside the towns?
No, this is a private transfer with stops for sightseeing and tastings. You’ll have free time to explore each town on your own.

Are the wine tastings included in the price?
Yes, the two wine tastings at Montepulciano’s historic cellars are included, along with explanations of the wines’ characteristics.

Can I customize the stops or the schedule?
Since it’s a private service, you can coordinate with your driver for preferred stops or timing, within the overall 8-hour window.

Is lunch included?
No, lunch is not included, but your driver can recommend good places to eat during the day.

What makes this experience good value?
Considering private transport, scenic stops, and wine tastings, the price offers a convenient and personalized way to enjoy Tuscany’s highlights efficiently.

How long are each of the stops?
Cortona gets about 1.5 hours, and Montepulciano about 2 hours, giving you enough time to walk around, take photos, and enjoy the tastings without feeling rushed.

Is this suitable for families or children?
While not specifically designed for kids, the activity is primarily sightseeing and wine tasting, which may not appeal to very young children. It’s best suited for adult travelers or older teenagers interested in wine and history.

Final Thoughts

This private transfer experience from Assisi to Florence, with stops in Cortona and Montepulciano, offers a relaxed, personalized way to enjoy some of Tuscany’s most photogenic towns and renowned wines. It’s perfect for travelers who love combining scenic drives with cultural stops and want the comfort and flexibility of private transportation.

The inclusion of wine tastings, stunning views, and local insights makes it a worthwhile addition to your itinerary, especially if you’re short on time. While it doesn’t include guided city tours, the freedom to explore at your own pace, paired with the expert driver’s local knowledge, makes it a practical and enjoyable choice.

If you’re after a more intimate, flexible experience that lets you savor Tuscany’s flavors and vistas without the fuss of navigating yourself, this could be just what you need. It’s a day that balances beauty, culture, and relaxation, crafted for those who want to make the most of a single day in this enchanting region.