Siena, Cortona, Montepulciano & Val D’Orcia from Florence – Semi private tour

Experience the Magic of Tuscany in a Day

If you’re craving a taste of Tuscany’s celebrated towns without the hassle of navigating on your own, this semi-private tour offers an excellent way to do so. For around $218 per person, you get an 11-hour journey through some of Italy’s most cinematic landscapes, including Siena, Cortona, Montepulciano, and the stunning Val D’Orcia. Led by engaging guides, you’ll travel comfortably in an 8-seat minivan, making stops that allow you to explore at your own pace.

What we love most about this experience are the personalized touches—small group size (just eight travelers maximum), and the chance to enjoy included wine tastings and a farm lunch. These elements create moments of genuine connection with Tuscany’s food, wine, and scenery. However, keep in mind that because of the extensive driving and free exploration, it’s a long day, and some might wish for more time in each location. This tour is best suited for curious travelers eager to see a variety of towns in a single day, with an interest in local food and wine.

Key Points

• Small Group Size: Only up to 8 people ensures an intimate experience and personalized attention.
• Flexible Exploration: Free time to wander in each town allows you to soak in the atmosphere at your own pace.
• All-Inclusive Tastings: Enjoy farm-fresh cured meats, bruschetta, and local wines, with a chance to visit a historic cellar.
• Comfortable Transportation: The 8-seat minivan makes for a smooth, scenic ride through Tuscany.
• Cinematic and Cultural Highlights: Visit towns famous from movies like Under the Tuscan Sun and Twilight.
• Impressive Landscapes: Drive through the Val D’Orcia, famed for its rolling hills and iconic cypress trees.

Discover the Heart of Tuscany: An In-Depth Review

Starting in Florence: Easy and Convenient

The tour kicks off early from central Florence—meet your guide, Andrea (if reviews are anything to go by, guides like him are full of stories, local insights, and enthusiasm). The departure at 7:45 am ensures you beat the crowds and get a full day in the Tuscan countryside. The journey begins with a scenic 1.5-hour drive through rolling hills, vineyards, and olive groves, setting the tone for the day ahead.

This ride isn’t just transportation—it’s part of the experience. As you settle into the minivan, you’ll enjoy the chance to relax, take pictures, and listen to your guide share tidbits about the area’s filming locations and history. From some reviews, the driver—Ned or Eduardo—are friendly and responsive, adding a friendly tone to the trip.

First Stop: The Charm of Cortona

Our first destination, Cortona, captures that perfect blend of medieval charm and artistic spirit. Thanks to Diane Lane’s portrayal of Frances Mayes in Under the Tuscan Sun, it’s become a must-see. You’ll have about an hour here—plenty of time to wander the narrow streets, browse artisan shops, and take photos of the city walls and panoramic views.

Reviews praise the town’s authentic feel, describing it as “a place where you might even start your own love story.” The town’s artisanal shops and scenic vistas are what make it so memorable. But be aware—if you’re visiting on a Sunday, some stores might be closed, as one reviewer noted. Still, the charm of Cortona lies in its old-world atmosphere, which doesn’t require shopping to enjoy.

A Farm Visit and Tasting: From Olive Groves to Cured Meats

Next, the tour takes you approximately 40 minutes to a local farm in the heart of Tuscany. Here, you’ll see semi-wild Cinta Senese pigs roaming freely and taste their curated farm products—think cured meats, bruschetta with garden-fresh ingredients, and local wine. This farm visit is a highlight for many travelers, offering an authentic taste of regional produce.

One reviewer described this as “an unforgettable experience,” emphasizing the farm’s exceptional products and the chance to enjoy a casual yet flavorful tasting board. The inclusion of wine at the farm enhances the experience, giving you a true sense of the local culinary tradition.

Montepulciano: The Town of Vampires and Fine Wine

After the farm, the journey continues about 40 minutes to Montepulciano, a hilltop gem with medieval streets, underground cellars, and stunning views. This is the town where vampires gather in the Twilight series, but beyond that, it’s renowned for its Vino Nobile di Montepulciano and DOCG wines.

With about two hours of free time, you can explore the Piazza Grande, the town’s main square, and even visit a 14th-century underground cellar for a complimentary wine and product tasting. Reviewers mention that guides like Andrea or Lorenzo provide local insights, making the visit both entertaining and educational.

Some travelers wished for more time here, especially to sit down with a glass of wine and soak in the atmosphere. Still, the included tasting at the cellar provides a memorable wine experience, often described as “wine tasting at a historic site”—a real highlight for wine lovers.

Experience the Iconic Landscapes of Val D’Orcia

Leaving Montepulciano, your ride takes you through the Val D’Orcia, a UNESCO World Heritage site famous for its rolling hills, cypress-lined roads, and postcard-perfect scenery. About an hour and a half are dedicated to just soaking in this landscape, which many say looks like a painting come to life.

The viewpoint offers plenty of time for photos—some reviewers mention how challenging it is to capture the scenery’s true beauty in photos but that simply being there is enough to leave a lasting impression.

Siena: A Medieval Wonder

Finally, the tour reaches Siena, a city famous for its medieval architecture, narrow streets, and the shell-shaped Piazza del Campo. The town served as a backdrop for movies like Letters to Juliet and Stealing Beauty. You’ll have about an hour to explore on your own—perfect for a quick walk, some gelato, or a photo of the cathedral.

Guests often say Siena is “the highlight of the day,” praising its authentic atmosphere and well-preserved historic center. Guides typically point out key sights like the Torre del Mangia and the Duomo, though the tour does not include a guided walk—leaving you free to soak in the ambiance at your own pace.

The Return Journey: Relaxing and Reflecting

After Siena, the coach heads back to Florence, with a roughly 1 hour 50-minute drive. Many reviews mention how the long day is well worth it, thanks to the stunning scenery, engaging guides, and the variety of towns visited. The return ride offers a chance for a nap or to chat with fellow travelers about the highlights of the day.

What’s Included and What’s Not?

The tour provides a light farm lunch, including cured meats and bruschetta, paired with local wines—an authentic, delicious, and cost-effective way to enjoy regional flavors. The wine tastings at the farm and in Montepulciano are included, often highlighted as a major value. Also, a guided tour leader is present throughout, sharing stories and tips.

However, note that guided walking tours of the towns are not included—your free time is just that, free. Also, transportation is by luxury minivan with a maximum of eight travelers, which makes for a cozy, less crowded experience.

Authentic Perspectives from Travelers

Reviewers consistently praise the knowledgeable guides—mentioning Andrea, Lorenzo, Dom, and Julia—who make the experience informative and fun. Many appreciate the personalized service and the flexibility of free exploration. Comments like “Alessandro made our trip so enjoyable,” and “Dom was amazing—friendly and full of stories,” highlight how meaningful a good guide can be.

The wine tastings and farm lunch get particularly enthusiastic feedback, with many saying they felt like they truly experienced the flavors of Tuscany. Some wished for more time in towns like Siena and Montepulciano to sit down with a drink or a meal, but most agree the balanced itinerary makes the most of a full day.

Considerations and Practical Tips

This tour involves a lot of driving, so it’s best suited for those comfortable with long days on the road. The free time in each town varies—around an hour in Cortona, two in Montepulciano, and just about an hour in Siena—so plan accordingly if you want to visit specific sites or sit down for a meal.

The price point offers excellent value, considering the included tastings, transport, and guided insights. Still, it’s a long day, so bring comfortable shoes, a hat, and some water. Keep in mind that lunch is light, so if you’re hungry, you might want to bring some extra snacks.

Who Should Consider This Tour?

This tour is perfect for travelers eager to see multiple towns without the stress of self-driving or planning multiple excursions. It suits those who appreciate authentic food and wine experiences and want to enjoy historic towns at a relaxed pace. If you’re looking for a comprehensive taste of Tuscany’s scenery, culture, and culinary delights—all within a day—this tour hits the mark.

However, if you prefer more structured guided visits or more time in each town, you might find it a bit rushed. It’s also ideal for those who appreciate small-group intimacy and flexibility.

Frequently Asked Questions

How long is the tour?
The tour lasts about 11 hours, starting early in Florence and returning around 8 pm.

What is included in the price?
Included are the transport in a luxury 8-seat minivan, light farm lunch, wine tastings at the farm and Montepulciano, and a guide providing local insights and stories.

Are guided walking tours of the towns included?
No, the tour provides free time for self-guided exploration, so you can wander at your own pace.

Is this tour suitable for all ages?
Most travelers can participate, but be aware that it involves long periods of driving and some uphill walking in towns.

How much free time do I get at each town?
Expect about an hour in Cortona, two hours in Montepulciano, and approximately an hour in Siena.

Can I buy wine during the tour?
Yes, the wine tastings are included, and you can purchase bottles if you wish.

What should I bring?
Comfortable shoes, sun protection, water, and perhaps a camera. Remember, lunch is light, so extra snacks might be welcomed.

What happens if I am ill or can’t make it?
Cancellations within 24 hours are not refunded, but the tour provider recommends contacting them if you have health issues; they may offer options depending on circumstances.

To sum it up, this semi-private tour offers a fantastic way to cover some of Tuscany’s most picturesque towns and landscapes in one memorable day. With small group sizes, knowledgeable guides, and inclusive tastings, it’s an excellent choice for curious travelers wanting authentic experiences without the hassle of self-driving. Perfect for those who value scenic beauty, good food, and a relaxed, flexible pace—just be prepared for a long but rewarding day in Italy’s charming countryside.