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

Traveling through Tuscany’s countryside is like flipping through a living postcard — rolling hills, ancient towns, and endless vineyards. If you’re looking for a way to see some of the region’s most iconic spots in a single day without the hassle of planning every detail, this guided tour from Florence might just be worth considering. We’ve looked into it, read plenty of reviews, and here’s a breakdown of what you can expect, what’s great, and what you might want to keep in mind.

Two things we love about this experience are its focus on local flavor—through wine tastings and farm visits—and the chance to explore some truly cinematic towns. Plus, the small-group setup seems to make the day feel personal and relaxed. That said, a possible drawback is that the schedule is quite packed, which means a lot of moving around and limited time at each stop. If you prefer a more leisurely pace or extra time in each town, this might feel a bit rushed.

This tour is a good fit for those who want a comprehensive taste of Tuscany’s highlights, especially if you’re keen on wine, scenic drives, and iconic film locations. It might not suit travelers with mobility issues or those seeking a slow, deep dive into a single town—but if you’re after a broad, scenic overview, it’s a solid pick.

Key Points

• Small-group experience: Typically in a private or small group setting, which tends to be more personalized.
• Comprehensive itinerary: Covers Cortona, Montepulciano, Siena, and the Val d’Orcia region, with plenty of photo stops and sightseeing.
• Cinematic towns: Visit places made famous by movies like Under the Tuscan Sun, Gladiator, and Letters to Juliet.
• Wine and food tastings: Enjoy local wines and farm products, including a visit to a family-run farm with an organized tasting.
• Scenic drives: Travel through some of Tuscany’s most beautiful landscapes, with plenty of opportunities for photos.
• Duration: About 10 to 12 hours, making it a full but manageable day trip from Florence.

You can check availability for your dates here:

A Closer Look at the Itinerary and Highlights

Starting Point and Transport

You’ll meet your guide at either the Parcheggio Oltrarno or a designated starting point in Florence, and from there, hop into a comfortable, private 8-seater minivan. This size is just right for maintaining a relaxed vibe while still feeling exclusive. The drive from Florence to your first stop, Cortona, takes around an hour and a half—scenic and pleasant, with views that might remind you of a film set.

Cortona: The Film Star

First stop is Cortona, perched on a hilltop with sweeping views of the Tuscan landscape. This is the town Diane Lane’s character falls in love with in Under the Tuscan Sun. The narrow streets, artisan shops, and notable landmarks are perfect for wandering and soaking up that authentic Italian vibe. Reviewers love how much time they get to explore, with one mentioning it’s a place where “you might even start your own Italian love story.” It’s a charming introduction to the region’s charm and history.

Farm Visit and Tasting

Next, you’ll venture about 40 minutes to a local farm in the heart of Tuscany. Here, you get the opportunity to walk among semi-wild Cinta Senese pigs, known for their high-quality meat, and stroll past olive groves and vineyards. The highlight? A tailored tasting board featuring cured meats and bruschetta made from ingredients straight from the garden, paired with the farm’s own wine. The reviews consistently praise this part as “the farm and the wine were amazing,” and many mention it as the standout experience of the day. One guest summed it up: “It was the first and best part of the day for our group, and the little piglets were adorable.”

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Montepulciano: The Vampires’ Town

After that, it’s time to visit Montepulciano, a picturesque walled town famous for its vampire scenes in Twilight (though likely less so for its mythical creatures!). This town is also renowned for its Vino Nobile di Montepulciano—a red wine that’s a favorite among wine lovers. Your guide will fill you in on the town’s history, the film scenes shot here, and other attractions. You’ll enjoy a complimentary wine tasting in a medieval underground cellar, which reviews often highlight as a memorable part of the trip. The town’s medieval charm, with its stone streets and commanding views, makes for excellent photo opportunities.

The Breathtaking Val d’Orcia

From Montepulciano, the journey continues into the Val d’Orcia region, a landscape that looks so perfect that it’s often used in travel magazines. Think rolling hills, lone cypress trees, and endless vineyards. The drive itself is a treat, and you’ll get a photo stop to capture this postcard scene. Many reviewers remark on how this part of the tour gives a real sense of Tuscany’s timeless beauty, and some even describe it as the highlight of the day.

Siena: The Medieval Gem

The last major stop is Siena, a medieval city with a reputation for its narrow streets, bustling squares, and historic charm. It features in movies like Letters to Juliet and Stealing Beauty, which only adds to its cinematic appeal. You’ll have about an hour and a half to wander, explore, and soak up the atmosphere. Reviewers frequently comment on how beautiful Siena is, especially as the sun sets and the city’s warm hues glow.

Return to Florence

Finally, the tour winds down with a scenic 1.5-hour drive back to Florence, giving everyone time to reflect on the day’s experiences and enjoy the countryside views. The tour concludes around 8 PM, making it a long but fulfilling day.

What Makes This Tour Stand Out

The guided aspect is a big draw — many reviews highlight knowledgeable, friendly guides like Francesca, Dom, and Antonello, who add depth and humor to the trip. The small-group format in a private minivan creates a more intimate and flexible experience, allowing for spontaneous stops and personalized attention.

The combination of cinematic history, local farm visits, and scenic landscapes makes this tour appealing if you’re after a well-rounded taste of Tuscany. The wine tastings, in particular, are often praised as “the best wines we tasted,” and reviews mention the value for money, noting that the experience feels generous and thoughtfully curated.

The scenery is truly breathtaking, with many guests commenting that the landscapes alone make the trip worthwhile. The carefully planned itinerary balances sightseeing, tasting, and relaxing drives, so you get a feel for both the towns and the countryside.

Things to Keep in Mind

While the experience is quite comprehensive, it’s worth noting that the schedule is tight. If you’re someone who prefers a slow pace or more time in each town, this might feel rushed. The tour is not suitable for people with walking disabilities or mobility issues, as it involves some walking and cobbled streets.

The roads can be curvy, as some reviews mention, so if you’re prone to motion sickness, it might be good to prepare accordingly. Also, given the early start and full day, it’s best suited for travelers who are comfortable with long days and a lot of moving around.

Pricing and Value

While the cost isn’t specified here, the reviews suggest that many find the value to be good, especially considering the included tastings, private farm tour, and guided visits. The small-group setup, knowledgeable guides, and tailored experience tend to justify a higher price point than large bus tours, making it attractive for those who prefer quality over quantity.

Final Thoughts

This tour offers an engaging way to see some of Tuscany’s most iconic towns with the added bonus of local wine and food experiences. It’s best suited for travelers who want a balanced mix of sightseeing, tasting, and scenic drives without the hassle of planning each stop. The small-group format and expert guides make it a comfortable way to learn about and appreciate the region.

If you’re after a full day of exploring, with plenty of opportunities for photos and tastings, and you don’t mind a busy schedule, this tour could be a highlight of your trip to Italy.

FAQ

Is this tour suitable for families with children?
This tour is more suitable for adults due to the walking involved and the full-day schedule. It’s not designed with children in mind.

What should I bring?
Comfortable shoes are recommended since there’s some walking on cobbled streets. Also, consider bringing a hat, water, and sunglasses for the outdoor parts.

How long is the drive from Florence?
It’s about 1.5 hours from Florence to Cortona, with additional driving to other stops, totaling around 10-12 hours overall.

Are the wine tastings free?
Yes, there are complimentary tastings included in the itinerary, often in historic cellars or at the farm.

Is the tour private or in a small group?
Both options are available; the reviews suggest a small-group experience, which enhances comfort and flexibility.

Can I customize or add extras?
The tour requires a minimum of 3 participants for a group experience; otherwise, a private tour with a surcharge may be offered.

Is the tour accessible for people with mobility issues?
No, it’s not suitable for people with walking disabilities due to walking on uneven streets and some stairs.

What if I have dietary restrictions?
Please inform your tour provider in advance so they can accommodate your needs, especially for tasting sessions.

How do I cancel if my plans change?
You can cancel up to 24 hours in advance for a full refund.

What’s the best time of year to do this tour?
While not specified, Tuscany’s landscapes are beautiful year-round, but spring and early fall generally offer the best weather.

In the end, this tour packs a lot into a single day — scenic views, cinematic towns, delicious wines, and local farm experiences — making it a popular choice for travelers eager to get a solid taste of Tuscany without a multi-day commitment. Just be ready for a busy but rewarding adventure.

You can check availability for your dates here: