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

Taking a full-day tour through Tuscany offers a wonderful way to see some of Italy’s most iconic towns without the hassle of planning multiple trips or driving yourself. This particular experience, offered by Italy on a Budget Tours, manages to strike a fine balance between guided expertise and free time, making it ideal for travelers who want a taste of Tuscany’s charm, scenery, and flavors.

What we love about this tour is how it combines stunning landscapes with authentic local food and wine—not to mention the chance to see film-famous locations like Cortona from Under the Tuscan Sun and Montepulciano, which gained fame through the Twilight saga. Also, the small group size (limited to 8 participants) promises more personal attention and a cozy atmosphere.

One thing to keep in mind is the long day’s schedule, which involves some early starts and a fair amount of driving. While the scenery and experiences make it worthwhile, travelers with mobility issues or those seeking a more leisurely pace might find it a bit intense. This tour suits those who love history, food, wine, and picturesque landscapes, and who are comfortable with a packed itinerary.

Key Points

• Small group size ensures personalized attention and a more intimate experience
• Expert guides provide rich insights about each location and local culture
• Incredible scenery through rolling hills, cypress-lined roads, and charming towns
• Authentic food and wine tastings on a traditional farm and in historic cellars
• Well-paced itinerary with ample time to explore each town independently
• Film locations that add a layer of pop culture to your Tuscany adventure

You can check availability for your dates here:

An In-Depth Look at the Tour Experience

This tour is designed to maximize your day in Tuscany by covering several highlights with a mix of guided commentary and free exploration. Starting early in Florence, you’ll meet your guide and hop into a comfortable private 8-seater minivan, perfect for small groups that want a more personal experience than big bus tours.

The Journey Begins: Scenic Drive and Cortona

The first leg of your day involves a scenic 1.5-hour drive through the Tuscan countryside—think rolling hills, patchwork fields, and cypress trees that seem straight out of a postcard. This landscape has delighted visitors for generations and is recognizable from movies like Under the Tuscan Sun.

Your first stop is Cortona, a stunning hilltop town made famous by Diane Lane’s character in the film. The town’s narrow streets, artisan shops, and ancient walls are the perfect introduction to Tuscany’s charm. We loved the way the guide shared tidbits about the town’s appearance in Frances Mayes’ novel, adding depth to the exploration. You’ll have about an hour here, enough to wander, take photos, or enjoy a coffee on a piazza.

Farm Visit and Tasting: A Taste of Local Life

Next, your journey takes you to a local farm—a highlight for many travelers. This isn’t just a stop for sightseeing but an immersive experience. You’ll walk among olive groves and vineyards, and see Cinta Senese pigs roaming semi-wild, a breed prized for its flavor and rarity. This farm is a showcase of authentic Tuscan food production.

Here, a carefully curated tasting board awaits, featuring cured meats and bruschetta made from garden ingredients, alongside their own wine. The reviews consistently praise this stop: one traveler noted, “The family gave us a tour of the farm then served us a lovely lunch with great wine and conversation.” It’s an authentic moment that offers both a sensory delight and insight into local artisanal traditions.

Montepulciano: Twilight’s Vampire Town

From the farm, the group heads to Montepulciano, about 1.5 hours away. This walled hilltop town is not only famous for its Vino Nobile and Montepulciano DOCG wine but also for its role in film—think Twilight’s Vampire Conclave.

Your guide will share local insights and movie trivia, making the experience more engaging. You’ll have time to explore at your own pace—winding alleys, charming squares, and panoramic views. Included is a complimentary wine tasting in a 14th-century underground cellar, giving you a taste of the region’s legendary wines.

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The Enchanting Val d’Orcia

After Montepulciano, you’ll journey through Val d’Orcia, a UNESCO-listed landscape of rolling hills, cypress-lined roads, and charming farms. Many travelers find this one of the most photogenic spots on the trip. The tour includes a photo stop to capture the quintessential Tuscan scene, which is perfect for sharing your trip on social media or just savoring the moment.

This part of the tour is more relaxed—giving you time to breathe in the views, snap photos, and appreciate the natural beauty that makes Tuscany so beloved.

Siena: Medieval Marvel

The final stop is Siena, famed for its medieval architecture and narrow streets. Thanks to its appearance in movies like Letters to Juliet, Siena has a romantic, storybook feel. You’ll have about 1.5 hours here, plenty of time to walk the piazzas, visit artisan shops, and soak in the atmosphere of this historic city.

The guide will point out key landmarks and share stories behind Siena’s historic sites. Reviewers rave about Siena as a highlight, describing it as “charming,” with “beautifully glowing” squares in the late afternoon sun.

Return to Florence

After a scenic 1.5-hour drive back, the tour concludes around 8:00 p.m., giving you a full day of exploration without feeling rushed.

What’s Included & What’s Not

This tour offers great value for the price of $186.92 per person, especially considering the transportation, guided insights, and multiple tastings included. The small group size makes for a more personal experience and allows the guide to tailor some commentary based on your interests.

Included are transport by minivan, an experienced tour leader, and wine and food tastings at both the farm and the underground cellar. The visits to Cortona, Montepulciano, and Siena are all timed to give you enough space to explore without feeling hurried.

However, note that hotel pick-up and drop-off are not included, which means you’ll need to meet at the designated starting point. The tour is not suitable for travelers with mobility issues or pregnant women, so be prepared for some walking and uneven streets.

Authentic Experiences That Make This Tour Stand Out

The reviews speak volumes about the quality of guides and the authenticity of the food and wine. One traveler noted, “Our guide, Dom, really made it a perfect day,” highlighting the importance of knowledgeable leadership. The farm visit and tasting are consistently praised as “memorable,” offering genuine insights into Tuscan food culture, not just a quick sample.

Many appreciated the ample free time—something that sets this apart from more rigid, timed tours. You’ll have opportunities for independent wandering, shopping, or simply soaking in the views, which many say enhances the overall experience.

Who Is This Tour Best For?

If you love history, food, wine, and scenic landscapes, this tour hits all the right notes. It’s especially great for small groups and those wanting a personal touch. Travelers who enjoy film locations and cultural landmarks will find it particularly engaging.

However, if you prefer a more relaxed pace or have walking difficulties, you might find the packed schedule a bit tiring. Still, for most, it offers a well-rounded slice of Tuscany’s best.

FAQ About This Tour

How early does the tour start?
The tour begins around 8:00 a.m., with exact times depending on your selected starting point.

Is transportation comfortable?
Yes, the tour uses a private 8-seater minivan, which offers a cozy and intimate ride through the countryside.

Are food and wine tastings included?
Absolutely. You’ll enjoy tastings at a traditional farm and in a historic underground cellar, featuring local wines, cured meats, and other products.

Can I explore the towns on my own?
Yes, the schedule allows free time for personal exploration—perfect for wandering, shopping, or taking photos.

Is this tour suitable for children or people with mobility issues?
It’s not suitable for people with mobility impairments and is better suited for adults comfortable with walking and a full day of sightseeing.

What about cancellations or flexible booking?
You can cancel up to 24 hours in advance for a full refund, and you can reserve now and pay later to keep your plans flexible.

Final Thoughts

This tour from Florence to Siena, Cortona, Montepulciano, and Val d’Orcia offers a well-curated slice of Tuscany’s beauty. The combination of stunning scenery, historic towns, and authentic food and wine makes it a strong choice for travelers eager to experience Italy’s heartland without the stress of self-driving.

The small group size and knowledgeable guides turn a busy day into a memorable journey filled with stories, flavors, and photo-worthy vistas. It’s perfect for those who want a guided experience with personal touches and some free time to wander and soak in the atmosphere.

While it’s a full day, many find that the value and quality of the sights, tastes, and stories make it a worthwhile investment. Whether it’s your first time in Tuscany or a return visit, this tour offers a well-rounded taste of Italy’s most enchanting region.

To sum it up, if you’re after an authentic, engaging, and scenic way to see Tuscany’s highlights—especially if you love wine, history, and film locations—this tour is a beautiful and practical choice. It balances guided insights with freedom to explore, making it an experience you’ll likely carry home in your memories for years.

You can check availability for your dates here: