From Florence: Siena, Cortona, Montepulciano & Val D’Orcia

Key Points

• Comprehensive 10-12 hour tour exploring Tuscany’s most famous towns including Siena, Cortona, and Montepulciano.
• Transport by private 8-seater mini-van, ensuring a comfortable and intimate experience.
• Highlights include film locations from Gladiator and Under the Tuscan Sun and visits to renowned wineries.
• Tastings of local wines, cured meats, and fresh bruschetta at a family farm and a 14th-century underground cellar.
• Ideal for those seeking a relaxed pace, with ample free time to explore each town independently.
• Small group or private options available, with expert guides leading the way.

You can check availability for your dates here:

Explore Tuscany’s Iconic Towns in a Full-Day Adventure

This full-day tour from Florence offers a carefully curated journey through some of Tuscany’s most charming and recognizable spots. Priced to include transport in a private 8-seater minivan and multiple tasting experiences, it’s perfect for those wanting an intimate, flexible look at the region’s highlights. The tour lasts about 10 to 12 hours, making it a long but fulfilling day for lovers of scenery, history, and good wine.

The tour begins early in the morning, departing from a choice of two central Florence meeting points. As the van winds through the Tuscan countryside, guests get to enjoy scenic views in comfort, setting the tone for a day filled with discovery. The experience is well-suited for travelers who prefer small groups or private experiences, with guides providing insights along the way and ample free time at each stop.

Discover Cortona, Famous for Under the Tuscan Sun

The first stop is Cortona, a picturesque hilltop town made famous by Diane Lane in Under the Tuscan Sun. Known for its narrow streets, artisan stores, and stunning views, Cortona invites visitors to explore at their own pace. The guide leads you through landmarks that Frances Mayes wrote about, giving a sense of the town’s charm and history.

With about one hour allocated to Cortona, visitors can stroll through its historic center, browse local shops, and take photos of the sweeping landscapes. The town’s reputation for olive groves adds a fragrant touch to the visit, and the film connection makes it a particularly memorable stop for movie fans and culture enthusiasts alike.

Farm Visit and Tasting of Tuscan Produce

From Cortona, the tour takes a short drive to a local farm in the heart of Tuscany. Here, Cinta Senese pigs roam semi-wild, and the farm’s olive groves and vineyards fill the landscape. This stop lasts about 1.5 hours, giving guests time to walk among the trees and enjoy the peaceful countryside.

On arrival, visitors are treated to a tasting board featuring cured meats and bruschetta made from garden-fresh ingredients, paired with the farm’s own wine. This experience is an authentic taste of local flavors, enhanced by the chance to learn about traditional farming practices. Many find this farm visit to be a highlight, offering a relaxed atmosphere and delicious bites.

Montepulciano and Its Film Fame

Next, the tour heads to Montepulciano, a striking walled town that served as a filming location for Twilight Saga: New Moon. This picturesque hilltop village is renowned not only for its Montepulciano DOCG wine but also for its medieval architecture.

Guests have about 1.5 hours here to explore the main square, shops, and historic streets. The guide shares stories about the town’s presence in films and local history, making the visit both educational and entertaining. A complimentary wine tasting in a 14th-century underground cellar adds a special touch, giving you a chance to sample regional wines amid historic surroundings.

More Great Tours Nearby

Marvel at the Val d’Orcia Landscape

After Montepulciano, the journey continues through the breathtaking scenery of Val d’Orcia. The landscape features rolling hills, cypress-lined roads, and lush farmland, offering some of the most iconic views of Tuscany.

Travelers enjoy a photo stop of around 15 minutes, where the landscape provides perfect photo opportunities. The van then transports you through the region’s scenic vistas, allowing a moment to appreciate the remarkable natural beauty of this area. The relaxed pacing ensures guests can take in each view without feeling rushed.

Siena’s Medieval Charm and Cinema Connections

The final town on the itinerary is Siena, a city full of history and film connections. Known for its narrow streets, medieval squares, and artisan shops, Siena is the backdrop for movies like Letters to Juliet and Stealing Beauty.

Guests have roughly 1.5 hours to explore Siena’s highlights, including its piazzas and historic streets. The guide points out landmarks and provides context about the city’s storied past. As the day winds down, the setting sun casts a warm glow over Siena’s medieval buildings, creating a memorable end to the tour.

Scenic Return Through Tuscan Countryside

After Siena, the tour takes a scenic 1.5-hour drive back to Florence. The return journey offers one last chance to enjoy the rolling hills and cypress trees, making the entire experience resonate with the timeless beauty of Tuscany.

The tour finishes around 8:00 pm at the initial meeting point, providing a full, rewarding day filled with culture, scenery, and regional flavors. The relaxed schedule and small group setting make it ideal for those who prefer a more personalized experience, with plenty of freedom to explore each town on your own.

Who Will Love This Tuscany Day Trip?

This tour is best suited for travelers looking for a comprehensive yet relaxed day exploring Tuscany’s most famous towns. It appeals to those interested in film locations, wine tasting, and authentic countryside experiences. The small group or private options ensure a personalized touch, making it a good choice for couples, friends, or small families.

While the tour involves walking through historic towns, it’s not designed for those with mobility impairments or walking disabilities. Guests should bring comfortable shoes and be prepared for curvy roads and scenic drives. The included tastings and farm visit provide a delicious insight into regional food and wine craftsmanship.

Why Choose This Tour Over Others?

Compared to larger bus tours, this experience offers a more intimate setting with only 6 guests in a minivan in many cases. Reviewers consistently highlight the knowledgeable guides, especially Francesca and Dom, who share local insights and personal stories. The balanced itinerary ensures enough time at each stop for self-guided exploration, avoiding rushed visits.

The tasting experiences—including farm products and underground cellar wines—add value beyond just sightseeing. The scenic drives through Val d’Orcia and stops at iconic towns like Cortona, Montepulciano, and Siena make this tour both visually stunning and culturally rich.

Frequently Asked Questions

Is this tour suitable for people with walking disabilities?
No, the tour requires walking and is not suitable for those with mobility impairments.

What should I bring for the day?
Comfortable shoes are recommended for walking on cobbled streets and uneven terrain.

Are dietary needs accommodated?
Yes, please inform the tour provider of any dietary restrictions in advance.

What is the duration of the tour?
The tour lasts approximately 10 to 12 hours, starting early in the morning and returning around 8:00 pm.

Can I cancel this tour?
Yes, free cancellation is available up to 24 hours in advance for a full refund.

Are there options for private tours?
Yes, private or small group options are available, with a supplement for private bookings if minimum numbers are not met.

What languages are guides available in?
Guides lead the tour in English.

Is lunch included?
Not explicitly, but the farm visit includes a tasting of cured meats and bruschetta, with wine, and there’s an optional gourmet lunch in other similar experiences.

What stops are included in the itinerary?
Stops are at Cortona, a farm in Tuscany, Montepulciano, Val d’Orcia, and Siena.

How scenic are the drives?
The drives through the Tuscan countryside are highly scenic, with plenty of opportunities for photos and enjoying views.

Can I join from San Gimignano?
Yes, the tour offers a starting point from Parcheggio Oltrarno in Florence or San Gimignano.

This well-reviewed, comprehensive tour provides a balanced combination of sightseeing, tasting, and scenery, ideal for those wanting a taste of Tuscany’s film history, wine culture, and landscape without feeling rushed.

You can check availability for your dates here: More Great Tours Nearby