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

Exploring Tuscany’s Treasures: Siena, Cortona, Montepulciano & Val d’Orcia from Florence

Traveling through Italy often means chasing iconic sights, but this semi-private tour offers a more relaxed, intimate way to experience Tuscany’s charm. Designed for small groups, with a cap of just eight travelers, it promises personalized attention and plenty of opportunities to soak in the scenery and local culture. From cinematic film locations to renowned wine regions, this day trip aims to tick off some of Tuscany’s most beloved towns with a good balance of guided insights and free exploration.

What we especially love about this tour is how it combines multiple highlights in one day — saving you the hassle of planning multiple trips — and the inclusion of a hearty light lunch and wine tastings, making it a well-rounded value. The chance to walk through towns like Siena and Montepulciano at your own pace, without feeling rushed, is another big plus. That said, keep in mind it’s a long day, with plenty of driving, so it suits travelers who enjoy scenic rides and are comfortable with a busy schedule.

If you’re after a taste of Tuscany’s authentic villages, with small-group intimacy and a focus on local flavors, this tour could be a perfect fit. However, if you prefer more extensive guided walking tours or want to explore each town in depth on your own, you might find it somewhat limited. Still, for a quick but genuine peek into the region’s beauty, this trip offers a memorable experience.

Key Points

• Small-group experience: Only up to 8 travelers for personalized service
• Authentic towns: Explore Siena, Cortona, and Montepulciano at your own pace
• Taste of Tuscany: Includes regional wine and product tastings, plus a light farm lunch
• Beautiful scenery: Journey through the Val d’Orcia, famous for its rolling hills and cypress trees
• Convenient transport: Roundtrip transportation from Florence saves time and effort
• Flexible free time: Ample opportunity to wander each town and soak in the atmosphere

The Itinerary in Detail

Meeting Point and Departure

The tour begins bright and early, with rendezvous at Porta Romana in central Florence at 7:45 am. Once everyone’s assembled, you’ll hop into a private 8-seat minivan, ready for an approximately 1.5-hour drive through Tuscany’s picturesque landscape. Listening to stories and facts from your guide, you’ll get a preview of what’s ahead — cypress-lined roads, fields of olives, and vineyards that look like they jumped straight out of a postcard.

Stop 1: Cortona

Your first stop is the hilltop village of Cortona, made famous by the movie Under the Tuscan Sun. Here, the narrow streets wind past artisan shops and historic landmarks, all with sweeping views of the surrounding countryside. You’ll have about an hour to explore independently — perfect for meandering, shopping for souvenirs, or just soaking in the medieval atmosphere. Reviewers note that Cortona’s charm is authentic, and the setting is truly picturesque, even if the shops may be closed on Sundays.

Stop 2: Montepulciano and its Farm

Next, you’re off to a working farm just 40 minutes away from Cortona. This is where things get delicious. Here, you’ll see semi-wild Cinta Senese pigs grazing on natural feed, and walk among olive groves and vineyards. The farm offers an all-inclusive tasting of local cured meats, bruschetta made from garden-fresh ingredients, and their own wine — a real treat for lovers of authentic Tuscan flavors. Reviewers appreciate this experience as a highlight, commenting on the chance to sample products directly from the farm and the quality of the wine.

Stop 3: Piazza Grande in Montepulciano

After the farm, it’s time to visit Montepulciano’s iconic Piazza Grande. This hilltop town is famous not only as the filming location for Twilight: New Moon but also for its renowned Vino Nobile di Montepulciano and Vino DOCG wines. Your guide will share insights about the town’s history, and you’ll have about two hours to explore freely. A highlight is the underground cellar near town entrance, where you can enjoy a complimentary tasting of local wines and delicacies. Visitors mention that the free time here is sufficient for a relaxed stroll, photo ops, and perhaps a glass of wine at a local cafe.

Scenic Drive through Val d’Orcia

Next, the van takes you through the breathtaking landscape of Val d’Orcia, famed for its rolling hills, terraced fields, and iconic cypress trees. You’ll have around 1.5 hours to enjoy the views — perfect for picture-taking and simply breathing in the tranquility of this UNESCO World Heritage site. Reviewers describe this part as a “heavenly” experience, with many saying the landscape alone makes the trip worthwhile.

Final Stop: Siena

The last town on the itinerary is Siena, a city that’s as charming as it is historic. Known as a filming location for movies like Letters to Juliet and Stealing Beauty, Siena’s medieval streets and grand piazzas leave a lasting impression. Your guide will escort you through the main piazza, the famous Piazza del Campo, before giving you roughly an hour of free time to explore. You may wish to visit sites like the Siena Cathedral or just enjoy the lively atmosphere of the city’s streets. Reviewers love Siena’s beauty and recommend taking time to enjoy its artisan shops and cafes.

Return to Florence

After a leisurely visit to Siena, you’ll hop back into the van for an approximately 1.5-hour ride back to Florence, arriving around 8 pm. It’s a long day, but the scenery, towns, and experiences make it worthwhile.

What’s Included and What’s Not

Included:

• All tasting experiences at the farm and cellar, including cured meats, bruschetta, and local wines.
• A light lunch featuring fresh ingredients.
• Transport in a comfortable, small 8-seat van.
• Free time in Cortona, Montepulciano, and Siena.
• The guidance of a knowledgeable local leader who provides context and stories along the way.

Not Included:

• Pick-up and drop-off from your accommodation — you’ll need to meet at the designated central Florence location.
• Guided walking tours of the towns — exploration is independent, giving you flexibility.

The Experience and Its Value

At $217.81 per person, this tour offers notable value considering the inclusions: wine tastings, a farm lunch, scenic drives, and visits to four compelling Tuscan locations. The small group size means more personal attention, and many reviews praise guides like Alessandro, Lorenzo, Dom, and Julia for their friendliness and info.

The timing is well-structured, allowing enough free time in each town to wander without feeling rushed. But be aware that the day is long — starting early and ending late — so this is best suited for travelers energized to spend a full day on the move. The drive itself, while scenic, involves a fair amount of time on the road, which some reviewers noted as a downside if you’re seeking more walking and guided commentary.

The included tastings, especially at the farm and in Montepulciano’s underground cellar, stand out as highlights, offering authentic flavors and insight into Tuscan wine culture. Many travelers found these experiences memorable, with some calling the wine tastings “amazing” and “well worth it.” However, some comment on the limited food options — the light lunch is simple bread, cheese, and bruschetta, so if you’re hungry, plan ahead.

Who This Tour Is Best For

This tour is ideal for travelers who want a rundown of Tuscany’s highlights without the hassle of organizing multiple transport or guided tours. Its small-group format fosters a relaxed atmosphere, perfect for those who appreciate personalized service and authentic experiences. Wine lovers will enjoy the tastings, and anyone interested in film locations or picturesque villages will find plenty to love.

It’s best suited for people comfortable with long days of sightseeing combined with scenic driving. If you prefer guided walking tours of each town or a more leisurely pace, you might find this a bit hurried. Conversely, if you’re eager for a taste of Tuscany’s best towns, stunning landscapes, and regional flavors in one day, this tour delivers.

FAQ

What time does the tour start?
The tour begins at 7:45 am at Porta Romana in Florence. It’s advisable to arrive early to ensure a smooth start.

Is transportation provided?
Yes, you’ll travel in a private, small 8-seat minivan, which makes for a more intimate and comfortable ride through Tuscany.

Are there guided walking tours in the towns?
No, the visits are self-guided, allowing you to explore each town at your own pace during the free time.

What’s included in the meals and tastings?
A light farm lunch with cured meats and bruschetta made from fresh ingredients, paired with the farm’s wine. There’s also a wine tasting at a 14th-century cellar, and tastings at the farm are all-inclusive.

How long is the total tour?
The entire day lasts approximately 11 hours, with travel, sightseeing, free time, and meals included.

What’s the group size?
The tour is capped at a maximum of eight people, ensuring personalized service and a relaxed atmosphere.

Can I book this tour on the day?
Most travelers book about 78 days in advance, but availability varies. It’s best to reserve early, especially in peak seasons.

Is there a minimum number of participants?
Yes, the tour requires at least three participants; otherwise, you might be offered a private tour at a supplement.

Are children or solo travelers welcome?
Yes, most travelers can participate, and solo travelers are often welcomed, especially given the small, friendly group size.

What if I need to cancel?
You can cancel up to 24 hours before the tour for a full refund, according to the policy.

In essence, this semi-private tour offers a well-balanced day of scenic drives, authentic towns, and regional flavors, perfect for those who want a manageable, authentic taste of Tuscany’s most photogenic and film-famous spots. The personalized touch, combined with regional tastings and free exploration time, makes it a worthwhile choice for anyone seeking a memorable small-group experience in Italy’s beloved countryside.