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

Planning a seamless journey between Assisi and Florence that also offers a taste of Tuscany’s beauty and flavors? This private transfer with stops in Cortona and Montepulciano promises just that — combining comfortable transportation, charming towns, and unforgettable wine experiences. It’s a thoughtfully curated way to escape the highway and explore some of Italy’s most captivating hilltop villages, without the worry of self-driving or group tours that feel rushed.

What really caught our eye was the carefully balanced itinerary — a leisurely visit to Cortona, famous as the filming location of Under the Tuscan Sun, followed by an in-depth look into Montepulciano’s renowned wines. Plus, the flexibility of a private service means you can customize or simply enjoy the day at your own pace. On the flip side, keep in mind that this tour doesn’t include lunch, so planning ahead will help you maximize your experience.

This experience suits travelers who love scenic drives, authentic small-town atmospheres, and wine tasting without the fuss of large-group tours. It’s perfect for those who want a personalized touch to their Tuscan journey while enjoying stunning vistas and cultural spots along the way.

Key Points

• Private and Comfortable: Tailored transport with a knowledgeable driver ensures a relaxed, personalized day.
• Authentic Tuscan Towns: Visit two of Italy’s most iconic hilltop villages, each brimming with history and charm.
• Wine Tasting Included: Enjoy guided visits to historic cellars with tastings of Vino Nobile di Montepulciano and other local wines.
• Flexible Stops: Optional stop at Lake Trasimeno adds a scenic natural touch, should you want it.
• Ideal for Food and Wine Lovers: The tour highlights Tuscan culinary traditions alongside wine, with restaurant recommendations for lunch.
• Value for Money: At around $290 per person, it offers a comprehensive, private experience blending sightseeing, culture, and wine.

An In-Depth Look at the Experience

The Journey Begins: Comfort and Flexibility

Starting from your choice of accommodation in Assisi or Perugia, you’ll be picked up by a private, air-conditioned vehicle. This setup means you avoid the hassle of navigating unfamiliar roads or sticking to tight group schedules. The drive itself offers a scenic preview of the rolling hills that define Tuscany, with the driver providing insights into the landscape — and, if you request, a possible stop at Lake Trasimeno. This large, tranquil lake is a treat for nature lovers, home to a variety of waterfowl and reed beds, making a quick detour well worth it for those wanting a nature break.

First Stop: Cortona — The Artistic and Film-Inspired Gem

At approximately 1 hour and 30 minutes into the drive, the first stop is Cortona, the quintessential Tuscan town made famous by the film Under the Tuscan Sun. With an elevation of 600 meters, the views from Cortona’s ancient walls sweep across the valley and Lake Trasimeno, giving visitors a perfect photo backdrop.

During your free visit, you’ll have a chance to stroll along narrow lanes lined with medieval buildings, visit charming piazzas, and see remnants from the Etruscan period, with the town’s original name, Curtun. The guide mentions the town’s deep roots in art, with connections to Renaissance artists like Luca Signorelli and Beato Angelico, as well as Baroque master Pietro di Cortona. Outside the city, the Hermitage of San Francesco (“Le Celle”) offers a peaceful retreat with spiritual and scenic appeal.

One reviewer appreciated the “nice drive from Assisi to Florence with stops in Cortona and Montepulciano that included a wine tasting,” emphasizing how the stops made the transfer feel more like a cultural excursion than just transportation.

Lunch Options and Recommendations

While the tour doesn’t include lunch, your driver will recommend good places to eat, allowing you to enjoy traditional dishes like pici pasta, local cheeses, or hearty Tuscan soups. Many travelers find that sampling regional specialties enhances the day, especially paired with the local wines.

Second Stop: Montepulciano — The Wine Capital

After a scenic drive through hilltop vineyards and olive groves, your next destination is Montepulciano, a medieval and Renaissance marvel. The town’s atmospheric streets, lined with Renaissance palaces and stone facades, set the perfect scene for a leisurely exploration.

The real highlight here, according to reviews and the tour’s focus, is the guided visit to historic cellars. You’ll see gigantic oak barrels holding Vino Nobile di Montepulciano DOCG, one of Italy’s most revered wines. A qualified winemaker will explain the wine’s characteristics, what makes it special, and how it’s crafted. The tasting experience is not just about sipping; it’s about understanding the depth of flavor, the aging process, and the tradition behind each glass.

One guest described the visit as “a wine tasting of the best wines, with an explanation of their basic characteristics,” and appreciated how the guide made the experience both educational and enjoyable. The underground cellars provide a cool, atmospheric setting that enhances the tasting experience, offering a glimpse into centuries-old wine-making traditions.

Authentic Tuscan Flavors and Cultural Riches

Beyond wine, Montepulciano is known for its culinary delights — from local pork and cheeses to honey and lentils. While the tour doesn’t include a meal, this stop is a great opportunity to indulge in a Tuscan lunch, either at a recommended restaurant or via your own exploration.

Drop-off in Florence — End of a Scenic Day

By late afternoon, your driver will take you directly to your Florence accommodation, ending a day filled with scenic vistas, historical insights, and delicious wines. The private nature of the transfer means you can relax and reflect on your day without feeling rushed, making it ideal for travelers who prefer comfort and flexibility.

Practical Details and Value

At $290.36 per person, this tour offers good value considering the personalized service, private transport, and included wine tastings. The small group or private setting allows for a more tailored experience, with the freedom to ask questions or linger at points of interest.

The duration is approximately 8 hours, which balances sightseeing and travel comfortably. The vehicle is air-conditioned, ensuring a pleasant journey through Tuscany’s sometimes hot landscape, especially in summer months.

The tour is suitable for most travelers, including those who may have mobility limitations, as the stops are mostly accessible, and the driver handles all logistics. Since lunch isn’t included, travelers should plan ahead — perhaps packing snacks or enjoying a meal in one of the towns.

What the Tour Includes:

• Private, air-conditioned vehicle
• Bottled water to stay refreshed
• Guided visits and tastings at two historic wine cellars
• Expert driver to navigate the scenic roads and provide local insights

What’s Not Included:

• Lunch (but driver will suggest good spots)
• Any additional personal purchases or extra activities

Authentic Insights from Reviewers

One reviewer, Julie_K, summed up the experience as “a very nice private drive from Assisi to Florence with stops in Cortona and Montepulciano that included a wine tasting,” highlighting how the stops made the journey more memorable. Her comment reflects the value of combining sightseeing with cultural and culinary experiences, rather than just a transfer.

Another aspect praised was the knowledgeable guides and the quality of the wine tastings, which added authenticity and depth to the visit. The underground cellars, with their colossal oak barrels, provide an immersive peek into traditional wine-making.

Who Will Love This Tour?

This experience is best suited for travelers who want a relaxed, private transfer that doubles as a cultural and gastronomic day trip. It works well for wine enthusiasts, history buffs, or anyone wanting a taste of Tuscany’s best without the crowds. It’s ideal for those who appreciate personalized service, scenic drives, and authentic small-town experiences.

If you’re looking for a quick, stress-free way to explore Tuscany’s hilltop towns and sample its wines, this tour hits the mark.

FAQs

Is this tour private or part of a group?
It’s a private transfer, so only your group will participate, offering a tailored experience.

How long is the total trip?
The total duration is approximately 8 hours, including stops, driving, and sightseeing.

Does the tour include lunch?
No, lunch isn’t included, but your driver will suggest good local spots to enjoy a traditional Tuscan meal.

Are the wine tastings suitable for non-drinkers?
While tastings involve sampling wine, non-drinkers can often opt for juice or still enjoy the cellar visits and explanations.

Can I customize the stops or activities?
The itinerary is set, but you can request to spend more or less time at each stop or ask about additional options during booking.

Is there a Lake Trasimeno stop available?
It’s a possible stop on request, as the drive passes near the lake; ask your driver if you’d like to include it.

Final Thoughts

This private transfer with stops in Cortona and Montepulciano offers a well-rounded taste of Tuscany’s beauty, culture, and flavors. It’s perfect for travelers who want a personalized experience, avoiding the bus crowds while still exploring iconic towns and enjoying excellent wines. The combination of scenic drives, cultural sights, and tasting sessions makes it more than just a transfer — it’s a mini-vacation within your Italian trip.

Travelers who value comfort, authenticity, and a bit of indulgence will find this experience offers a delightful balance between sightseeing and relaxation. Whether you’re a first-time visitor or returning to Tuscany, this day trip provides a meaningful way to connect with the region’s essence without feeling rushed or overwhelmed.

If you’re after a hassle-free, intimate way to enjoy the Tuscan countryside, this tour might just become a highlight of your Italian adventure.