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

An Authentic Journey from Assisi to Florence with Stops in Cortona & Montepulciano

Traveling through Italy’s rolling hills and picturesque towns doesn’t have to be complicated or crowded. This private transfer from Assisi to Florence offers an excellent way to see some of Tuscany’s most captivating sights without the hassle of self-driving or group tours. For $290.36 per person, you get a full-day experience that combines scenic drives, historical exploration, and wine tasting — with the flexibility and intimacy of a private guide.

What we love most about this tour is how it blends culture with comfort. The driver, who acts more like a knowledgeable host, takes you through landscapes that seem to be carved out of a postcard. Plus, the stops at Cortona and Montepulciano are thoughtfully curated: you’ll enjoy free time to wander, explore local sights, and sample some of Tuscany’s most famous wines. The second highlight? The authentic, behind-the-scenes visits to historic cellars—a rare chance to see massive oak barrels and learn what makes Vino Nobile di Montepulciano so special.

One thing to keep in mind is that lunch isn’t included, so you’ll want to accept the driver’s recommendations for a delicious Tuscan meal. Also, since this is a private transfer, the timing and pace are flexible, which is ideal if you want to linger longer in a certain town. This experience suits travelers who value comfort, local insight, and a taste of Italy’s rural beauty — especially those eager to combine sightseeing with wine tasting and authentic local flavor.

Key Points

• Personalized Experience: The private vehicle and driver ensure a flexible, intimate journey tailored to your pace.
• Authentic Stops: Explore Cortona’s Etruscan roots and Montepulciano’s renowned wine cellars, with free time to soak in the atmosphere.
• Scenic Drives: Enjoy a comfortable ride through Tuscany’s famous rolling hills, cypress-lined roads, and lush countryside.
• Cultural & Culinary Highlights: Discover historic sites and indulge in wine tastings, with the driver ready to recommend local eateries.
• Perfect for Wine Lovers: Visit two historic cellars and taste regional wines, including Vino Nobile di Montepulciano.
• Convenience & Value: All logistics handled, with bottled water included and optional stop at Lake Trasimeno.

A Detailed Look at This Tuscany Transfer Experience

Setting the Scene: Why This Tour Works

This private transfer stands out because it’s not just about getting from Assisi to Florence — it’s about the journey itself. The route takes you through the heart of Tuscany, giving a real taste of the landscape that has enchanted visitors for centuries. For roughly 8 hours, you’ll be immersed in views of vineyards, olive groves, and medieval towns, all from the comfort of a well-maintained, air-conditioned vehicle.

The driver, often described as very knowledgeable, acts as your guide, sharing insights about the towns and region along the way. This makes the experience richer than just a transfer. You’re treated to a tailored introduction to local culture and history, making it perfect for travelers who want more than just transportation.

The Stops: Cortona and Montepulciano

Cortona: Etruscan Charm with Artistic Flair

Your first stop is Cortona, a town famous for its Etruscan origins and Renaissance connections. Sitting at about 600 meters above sea level, it offers panoramic views you’ll love to photograph. As you stroll through its narrow streets, you’ll notice remnants of its Etruscan past—like ancient walls and artifacts—intertwined with Renaissance art and architecture.

Julie_K mentioned in her review that she appreciated the “nice drive” with a stop in Cortona, noting its picturesque setting and artistic appeal. Outside the town, the Hermitage of San Francesco (“Le Celle”) provides a peaceful spot to reflect and enjoy the countryside.

The free visit lasts about 1.5 hours, which is enough time to wander, take in the views, maybe browse some local shops, and enjoy the relaxed Tuscan atmosphere.

Montepulciano: Medieval Elegance & Wine Heritage

Next, you’ll head to Montepulciano, a medieval and Renaissance hill town famed for its architecture and, most notably, its world-class wines. This stop combines sightseeing with a deep dive into regional winemaking traditions.

You’ll visit two historic cellars, where a qualified winemaker shows you colossal oak barrels filled with Vino Nobile di Montepulciano DOCG and Rosso di Montepulciano. The guided tasting that follows is a highlight — you’ll get to savor these wines and learn what sets them apart. The underground cellars add to the authenticity, echoing centuries of tradition.

According to the reviews, the wine tastings are highly praised. One reviewer appreciated the “delicious wine tasting of the best wines,” and the detailed explanation of their characteristics added to the experience. There’s also time to explore the town’s medieval streets, towers, and piazzas, giving a well-rounded visit.

The Scenic Drive & Optional Lake Trasimeno Stop

The drive itself deserves mention. Passing near Lake Trasimeno, travelers can request a stop — a wonderful opportunity to enjoy Italy’s largest lake, with its reed beds and water lilies. The scenery from the car window is stunning, making the journey as memorable as the stops.

Practical Details & What’s Included

The air-conditioned vehicle and bottled water keep you comfortable throughout the day. The two wine tastings in Montepulciano, with explanations, are included in the price — a real bonus considering how expensive wine tastings can be in Italy.

While lunch isn’t included, the driver will point out excellent places to eat, which means you can choose a meal that suits your taste and budget. This flexibility is ideal for those who prefer casual trattorias or local osterias over touristy spots.

Analyzing the Value and Suitability

At $290.36 per person, this tour offers a lot of value, especially considering the private transportation, guided visits, and tastings. For travelers eager to combine sightseeing with a personalized experience and culinary delights, it’s a smart choice.

Several reviews mention how the knowledgeable driver made the trip engaging and informative. The stunning views and authentic visits give a genuine taste of Tuscany, far from cookie-cutter tours. It’s especially suitable for those who want a relaxed pace and the ability to customize the stops slightly.

One potential drawback is the absence of lunch included, but for many, this allows the flexibility to explore local cuisine on their own, making the overall experience feel less rushed. Since most travelers seem very satisfied, it’s clear this tour hits the sweet spot for those looking to combine comfort, culture, and flavor.

Who Should Consider This Tour?

This experience is perfect for wine enthusiasts, history buffs, and photographers alike. It’s especially suited to travelers who prefer a private, flexible itinerary over rigid group tours. If you love discovering towns at your own pace, savoring regional wines, and enjoying breathtaking views without the stress of driving, this is a great option.

It also appeals to those who want a taste of Tuscany’s countryside, with enough time to explore without feeling hurried. Whether you’re coming from Assisi or Perugia, this tour makes the most of a day, offering a blend of cultural highlights and scenic beauty that captures Tuscany’s essence.

FAQs

Is this a group tour or private?
This is a private transfer, meaning only your group participates, allowing for a more personalized experience and flexibility.

How long is the tour?
The tour lasts approximately 8 hours, giving you plenty of time to explore both towns and enjoy the scenery.

Are the wine tastings included?
Yes, the wine tastings at two historic cellars in Montepulciano are included in the price. You’ll learn about regional wines and taste some of the best.

Can I request a stop at Lake Trasimeno?
Yes, a stop at Lake Trasimeno can be requested, providing extra time to enjoy the lake’s natural beauty.

Is lunch included in the tour?
No, lunch is not included, but your driver will recommend good local spots to enjoy authentic Tuscan cuisine.

What kind of vehicle will I ride in?
An air-conditioned vehicle suitable for your group size ensures a comfortable ride through the Tuscan countryside.

Who is the driver?
The driver acts as your local guide, providing insights about the towns and region along the way.

Is this suitable for all travelers?
Most travelers can participate, but those with mobility issues should check with the provider since walking in towns may vary.

Final Thoughts

This private transfer from Assisi to Florence with stops in Cortona and Montepulciano offers a balanced mix of scenic drives, cultural discovery, and wine tasting—perfect for travelers wanting to see Tuscany’s highlights comfortably and authentically. The experience provides a meaningful glimpse into Italy’s rural charm, away from crowded bus tours, with the added bonus of personalized attention and expert guidance.

You’ll love the panoramic views, the chance to explore historic towns at your own pace, and the opportunity to taste local wines straight from century-old barrels. It’s a flexible, tasteful way to deepen your understanding of Tuscany’s landscape and traditions, making your trip all the more memorable.

This tour is especially suited to those who value authentic experiences, enjoy good conversation with knowledgeable guides, and want to combine sightseeing with delicious wine and regional food. It’s a fantastic choice if you’re looking to experience Tuscany in a relaxed, authentic way—without sacrificing comfort or quality.