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

Exploring Tuscany can feel overwhelming with so many towns and scenic spots vying for your attention. This semi-private tour from Florence promises a well-balanced day, visiting four iconic locations—Siena, Cortona, Montepulciano, and the stunning Val d’Orcia—while offering just enough free time to soak in the atmosphere, taste local wines, and snap some photos.

What we love about this experience is how it combines personalized service—with a small group capped at eight travelers—and the opportunity to visit film-famous and authentic towns without the hassle of planning transportation. The inclusion of light lunch and wine tastings adds genuine value, making it more than just a sightseeing trip.

One potential downside? The full-day schedule involves quite a bit of driving and walking, so if you’re not a fan of long days or uphill cobblestone streets, this might be a bit tiring. However, for lovers of scenic landscapes, Italian towns, and good wine, this trip is a fantastic pick, especially for those wanting a taste of Tuscany’s best in a relaxed, flexible setting.

Key Points

• Small-group approach ensures personalized attention and a more intimate experience
• Flexible free time in each town allows for personal exploration
• Inclusion of wine tasting and local products elevates the overall value
• Comfortable transportation in a private mini-van helps maximize sightseeing
• Ideal for lovers of film locations, wine, and scenic landscapes
• Most travelers find it well worth the price for the comprehensive experience

A Deep Dive into the Experience

Starting Point and Transport

The tour kicks off early at Porta Romana in Florence—meet your guide around 7:45 am, ready to leave at 8:00 am. The small group of just eight people means you get a more personalized vibe, avoiding the chaos of larger buses. Traveling in a luxury 8-seat mini-van, the ride through Tuscany’s rolling hills is a highlight in itself.

A few reviewers have noted that the driver, while friendly, wasn’t a guide and provided minimal commentary. Still, this setup offers a smooth journey, giving you plenty of window time to take in the changing scenery and chat with fellow travelers.

Cortona: Film Fame and Authentic Charm

The first stop is Cortona, perched on a hilltop with narrow streets and artisan shops. Known worldwide thanks to Under the Tuscan Sun, this town exudes a relaxed, authentic vibe. Reviewers are quick to mention its appeal: “It’s the place where they filmed Under the Tuscan Sun and is loved for its medieval charm,” one noted.

You get about an hour to explore independently, which is enough to walk the cobblestone streets, peek into small stores, or snap photos of gorgeous views. However, some travelers wish for more time—particularly to sit down for a coffee or light snack. The town is quite compact, so even an hour can be satisfying if you’re efficient with your sightseeing.

Montepulciano: The Wine and Film Connection

Next, the journey takes you to Montepulciano, famous for its Vampires—yes, the town featured in Twilight: New Moon—and its renowned Vino Nobile di Montepulciano DOCG. Here, the highlight is a farm visit, where you can stroll among olive groves and vineyards, and enjoy a tasting board of cured meats and bruschetta made from fresh garden ingredients.

One reviewer mentions that they appreciated how the farm products were exceptional, paired with their own wines, making the experience both delicious and memorable. Plus, a complimentary tasting at a 14th-century cellar adds a fun historical touch. You get about an hour and a half here, which is enough time to explore the farm and indulge in tasting.

Exploring Montepulciano’s Piazza Grande

After the farm, the town of Montepulciano itself becomes the focus. The Piazza Grande offers stunning views over the countryside and was used in several film scenes. The town’s medieval architecture, terracotta rooftops, and atmospheric streets make it a photographer’s dream.

The guide provides local insights—like the connection to film scenes—and you’re free to wander for around two hours. A highlight for many: the visit to an underground cellar, where you can taste local wines and products as part of the experience. Several reviews note that the free time here is well spent, even if some wished for more time to enjoy a leisurely lunch or a glass of wine at a local café.

The Heart of the Tuscan Landscape: Val d’Orcia

As you leave Montepulciano, your journey continues through Val d’Orcia, a UNESCO World Heritage site famous for its rolling hills, cypress trees, and idyllic vistas that appear in countless travel magazines.

Travelers often comment on how breathtaking the scenery is—making it clear why it’s a film favorite. The hour and a half here offers a chance to relax, take photos, and soak in the scenery. It’s one of the most valued parts of the trip, with many reviewers describing it as heavenly or the essence of Tuscany.

Siena: Medieval Charm and Film Fame

Your final stop is Siena, a city with a medieval skyline, narrow streets, and a vibrant square—Piazza del Campo—that’s perfect for photos. Siena has starred in movies like Letters to Juliet and Stealing Beauty, and it’s easy to see why.

You’re given about an hour and fifty minutes to explore on your own. Many reviewers praise the city’s charming atmosphere, and some mention that they appreciated the guided walk with the guide pointing out film locations and sharing local stories.

Return Journey and Overall Experience

After Siena, the group heads back to Florence, with the van making the return trip by around 8 pm. This long but scenic drive is a chance to reflect on the day, with most guests feeling they’ve packed in a lot of sightseeing and authentic experiences into a single day.

What’s Included and What’s Not

For about $217 per person, you get a lot of value. The price includes:

• Snacks and tastings at the farm, featuring cured meats and bruschetta paired with wine
• A wine tasting at a 14th-century cellar
• Transport in a luxury mini-van
• Independent exploration in Cortona, Montepulciano, and Siena

However, the tour doesn’t include guided walking tours of each town, so you’re on your own to discover the streets. There’s no included lunch—just the light farm snacks—so if you’re expecting a sit-down meal, plan accordingly.

Some reviews point out minor frustrations: the long day can be tiring, especially with shorter free times. Also, the guides are not licensed tour guides, which means the commentary is more general, though many reviewers still appreciated the local insights and stories shared.

Authentic Experiences That Stand Out

Reviewers repeatedly mention the knowledgeable guides—like Alessandro, Lorenza, Dom, and Eduardo—who bring enthusiasm, local tips, and personal touches to the trip. The wine tastings were a highlight for many, with some waking up with a newfound appreciation for Tuscan wines.

The scenery is, of course, a major draw, with many guests describing the landscapes as “incredible,” “beautiful,” or “heaven on earth.” The visits to towns featured in popular films are a big appeal—adding a layer of pop culture to the authentic streets and squares.

Practical Tips for Future Travelers

• Bring comfortable shoes: towns like Cortona and Siena involve uphill walks on cobblestones.
• Expect a full day: start early and be prepared for a long, scenic trip.
• Allocate extra funds if you want to buy wine or local products; the tasting opportunities are fantastic but shopping is on your own.
• Plan meals accordingly: the included snacks are light, so consider bringing a small picnic or eating beforehand.
• Expect flexibility: the order of stops may change to optimize the experience.

Who This Tour Is Best For

This tour is ideal for travelers who want a comprehensive taste of Tuscany without the hassle of driving or planning logistics. The small group size ensures a more intimate experience, and the mix of film locations, scenic landscapes, and wine hits many of the region’s highlights. It suits those who appreciate authentic towns but don’t mind a busy schedule, as well as wine lovers eager to sample local flavors.

If you’re looking for an in-depth guided tour with detailed historical insights, this might not be your best option since the guides aren’t licensed guides. However, if you want a relaxed yet structured day with plenty of flexibility to explore on your own, this is a fantastic choice.

FAQ

Is transportation included?
Yes, you travel in a private 8-seat mini-van, making it comfortable and efficient for the day’s journey.

How long is the overall tour?
The full experience lasts approximately 11 hours, including travel, sightseeing, and free time.

Are meals included?
No, there’s a light farm snack and wine tastings, but no full meal is provided. You might want to bring extra snacks or plan to eat in Siena.

Can I customize the stops?
The itinerary is fixed but can occasionally change to ensure the best experience. The stops in Cortona, Montepulciano, and Siena are fixed, with free time allocated for exploration.

Is this suitable for all ages?
Yes, but keep in mind that towns involve some uphill walking and cobblestones. It’s best suited for travelers who can handle a full day on their feet.

What if I want a guided tour of each town?
This tour does not include guided walking tours; it’s mainly independent exploration with a small group and driver.

How much free time do I get?
Approximately 1 hour in Cortona, 2 hours in Montepulciano, and nearly 2 hours in Siena, giving you chances to explore, shop, or relax.

Is the wine tasting worth it?
Absolutely. Several guests highlight the quality of the tastings and the chance to enjoy local wines in atmospheric settings.

Final Thoughts

This semi-private Tuscany tour from Florence offers an excellent balance of sightseeing, cultural insight, and leisure. The small group size, combined with the scenic drives and curated stops, makes it a memorable way to experience some of Italy’s most beloved towns and landscapes.

While it involves a fairly packed schedule and some basic guidance, the authentic towns, beautiful scenery, and wine experiences truly shine through. It’s perfect for those who want to see Tuscany’s highlights without feeling rushed or overwhelmed, especially if you enjoy a bit of film history and local flavor.

If you’re seeking an authentic, flexible, and scenic Tuscan adventure that provides a good mix of guided and self-guided moments, this tour stands out as a well-rounded option. Just be prepared for a full day of sightseeing and a fair amount of walking, and you’ll likely walk away with not only beautiful memories but a deeper appreciation for Tuscany’s charm.