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

Explore Tuscany with a Private Assisi to Florence Transfer Including Stops in Cortona & Montepulciano

This private transfer from Assisi to Florence offers more than just a ride — it’s a full-day adventure through some of Tuscany’s most charming hilltop towns. Priced at $290.36 per person, this journey features stops in Cortona and Montepulciano, with wine tastings and opportunities to explore historic sites. The 8-hour trip is ideal for those seeking a personalized experience with pickup included and the flexibility to enjoy key highlights at a relaxed pace.

What makes this tour stand out is its focus on local culture and wines, combined with scenic views of rolling hills and ancient towns. The driver leads the way, offering recommendations for lunch and guiding you through two historic cellars. This is a perfect choice for travelers wanting a tailored transfer that combines sightseeing, flavor, and convenience.

Key Points

• Private, customizable transfer from Assisi to Florence with stops in Cortona and Montepulciano
• Includes guided wine tastings at two historic cellars in Montepulciano
• Stops at scenic locations like Trasimeno Lake, with optional visits on request
• Duration of approximately 8 hours, with pickup from your accommodation
• Cost of $290.36 per person, with group discounts available
• Free cancellation up to 24 hours before the tour

Starting Your Day with a Convenient Pickup in Assisi

The tour begins with a pickup at your hotel, B&B, or private apartment in Assisi or Perugia, providing a seamless start to your day. The air-conditioned vehicle ensures comfort during the drive through the gentle, rolling hills of Umbria and Tuscany. The driver acts as both guide and chauffeur, sharing insights about the landscape and the towns you’ll pass en route to Cortona.

This personalized transfer makes it easy to relax and enjoy the scenery while avoiding the hassle of navigating public transport or multiple bookings. The group size remains small and exclusive, enhancing the intimate feel of the experience.

Scenic Drive Near Lake Trasimeno and the Rolling Hills of Tuscany

As the journey progresses, you’ll pass near Trasimeno Lake, a large natural body of water in the heart of Umbria. While a stop is optional and available on request, the lake’s beds of reeds, white water lilies, and wildlife offer picturesque views along the way. The drive through the undulating landscape gives a true sense of Tuscany’s iconic scenery—cypress-lined avenues and medieval towns dot the countryside.

This scenic route sets the perfect tone for the day, combining natural beauty with the anticipation of exploring historic sites. The travel time is optimized for comfort and sightseeing, without rushing through the highlights.

Discovering the Artistic Charm of Cortona

The first stop is Cortona, a 600-meter-high hilltown famed for its Etruscan origins and Renaissance art. The town still bears original remains from its ancient past, visible in its streets and ruins. Visitors can stroll through Cortona’s historic center, enjoying views of the Val di Chiana and Lake Trasimeno.

Cortona gained additional fame as the setting for the film Under the Tuscan Sun, and its cultural richness is apparent in sites like the Hermitage of San Francesco at Le Celle. This 1 hour 30 minutes stop offers a free visit, giving ample time to admire the medieval architecture, artistic works, and panoramic vistas.

The guide shares stories about the town’s Etruscan roots, Renaissance artists like Luca Signorelli and Beato Angelico, and Baroque influences from Pietro di Cortona. This stop is ideal for those interested in history, art, and photography.

Tasting Tuscan Wines in Montepulciano’s Historic Cellars

After Cortona, the journey continues towards Montepulciano, a medieval and Renaissance hilltown renowned for its wine and culinary specialties. This stop is a highlight for wine lovers, as it includes two guided visits to historic cellars.

Within the cellars, visitors observe gigantic oak barrels that hold Vino Nobile di Montepulciano DOCG—a local red wine with a distinctive flavor profile. The expert guide explains the characteristics of the wine, including its production process and aging techniques. Following the visits, a wine tasting features the best wines of the region, including Rosso di Montepulciano and Super Tuscan varieties like Brunello of Montalcino.

This experience offers a chance to learn about Tuscan wine traditions firsthand and enjoy tastings that highlight the regional terroir. The 2-hour stop balances exploration with relaxation, making it suitable for those eager to combine cultural sightseeing with gastronomic delights.

Enjoying Free Time in Montepulciano

Beyond the wine cellars, Montepulciano itself invites wandering its medieval streets. The town is famous for its pork, cheese, pici pasta, lentils, and honey, which reflect its culinary heritage. Visitors can explore the historic center, take photos of medieval towers and churches, or simply enjoy the atmosphere in one of the town’s piazzas.

While the tour includes guided wine tastings, there’s ample free time to stroll, shop, or sample local delicacies at your own pace. The driver is available for recommendations on where to dine or explore further.

Seamless Drop-Off in Florence at the End of the Day

After an immersive day in Tuscany’s artistic towns and wine regions, the private vehicle drops off guests directly at their Florence accommodation. The 8-hour itinerary ensures enough time to see highlights, taste wines, and enjoy scenic views without feeling hurried.

This door-to-door service offers the convenience of avoiding public transport and allows for a customized pace, making it ideal for luxury or independent travelers seeking a relaxed experience.

Practical Details: What’s Included and What’s Not

The tour price covers air-conditioned transport, bottled water, and two wine tastings at historic cellars. It also includes visits to Cortona and Montepulciano, with free time and guided explanations where applicable.

Lunch is not included, but the driver recommends excellent spots for a Tuscan meal. The tour is designed as a private activity, meaning only your group participates, enhancing personalized attention.

Who Will Appreciate This Tour Most

This private transfer suits those interested in art, history, and wine who want a flexible and comfortable way to explore Tuscany’s highlights. The small group size and personalized service make it ideal for couples, families, or small groups looking for an intimate experience with local flavor.

The 8-hour duration balances sightseeing with relaxation, but travelers should be prepared for walking, especially in hilly towns like Cortona and Montepulciano. Those seeking a more leisurely, wine-focused day will especially enjoy the guided cellar visits and tastings.

The Value and Unique Selling Points of the Tour

Priced at $290.36 per person, this tour offers a comprehensive way to see two iconic Tuscan towns with expert-guided wine tastings included. The pickup service and private vehicle ensure comfort and convenience, avoiding the hassle of self-driving or multiple bookings.

What sets this tour apart is its focus on local culture and flavors, combined with scenic drives and artistic stops. The flexibility to request stops like Trasimeno Lake adds to its appeal. The high rating of 5.0 and positive review highlight the reliability and quality of the experience.

Final Thoughts on the Assisi to Florence Private Transfer with Stops

This 8-hour private transfer offers value for travelers seeking a personalized, scenic, and culturally enriching day in Tuscany. It’s especially suitable for those who want to combine artistic sightseeing with wine tasting and avoid the constraints of group tours.

The tour’s strengths lie in its customizable nature, the beautiful towns of Cortona and Montepulciano, and the expert guidance during wine cellar visits. Its main limitation might be the lack of included lunch, but this allows for personal choice and flexibility.

This tour is ideal for independent-minded travelers eager to enjoy Tuscany’s authentic sights and flavors at their own pace.

Frequently Asked Questions

Is lunch included in this tour?
No, lunch is not included, but the driver recommends excellent places to eat in Tuscany.

Can I request stops at Trasimeno Lake?
Yes, a stop at Trasimeno Lake is possible upon request, as the route passes near it.

How long are the visits in Cortona and Montepulciano?
Cortona is visited for approximately 1 hour 30 minutes, and Montepulciano for about 2 hours, including wine cellar tours and tasting.

What wines are tasted during the tour?
Tastings include Red wine of Montepulciano, Nobile di Montepulciano DOCG, Super Tuscan, and Brunello of Montalcino.

Is this tour suitable for all ages?
Most travelers can participate; physical requirements are minimal but involve some walking in hilly towns.

What is the cost of this tour?
The price is $290.36 per person, with options for group discounts.

How do I cancel or reschedule?
Cancellation is free up to 24 hours before the start; changes less than 24 hours prior are not accepted.

Who is the provider of this tour?
The experience is operated by Pek Tuscany in Limo, contactable at +393892521054 or [email protected].