Tuscany Wine & Hills from Siena

Thinking about a day out in Tuscany that combines stunning scenery, charming towns, and some wine tasting? This Tuscany Wine & Hills tour from Siena offers exactly that—though, like any experience, it has its highs and lows. We’ve looked into what this tour entails to help you decide if it fits your idea of a perfect day in Italy’s renowned wine country.

What we really like about this experience is the opportunity to explore two UNESCO-listed towns, Pienza and Montepulciano, at your own pace. Plus, the wine tastings are genuinely a highlight—many reviews praise the quality of the wines and the knowledge of the guides. On the flip side, some find the overall organization a bit uneven, especially concerning transportation and itinerary details, so it’s worth considering what you want from a day trip.

This tour is best suited for travelers who love scenic drives, wandering charming streets, and tasting quality local wines without the hassle of planning every detail themselves. If you’re ok with a more flexible, somewhat guided experience that emphasizes leisure and sightseeing over deep historical immersion, this could be a good fit. Keep in mind, it’s not a luxury or small-group tour—group sizes can reach up to 50 people, which can affect the intimacy and pace.

Key Points

• Flexible exploration: You get free time in Pienza and Montepulciano to wander at your own pace.
• Wine highlights: Tasting Chianti and Nobile di Montepulciano at carefully chosen cellars.
• Scenic views: The drive through Val d’Orcia offers postcard-worthy scenery.
• Mixed reviews on transportation: Some travelers mention subpar vehicles, so comfort might vary.
• Tour duration: Around 10 hours, making for a full but manageable day.
• Price point: About $147.88 per person, which many say offers good value considering the included tastings and visits.

What’s Included and What’s Not

This tour covers transportation by air-conditioned coach or minivan, guided commentary in multiple languages, and wine tastings with snacks. You’ll visit Fattoria Lornano for Chianti wine and a wine cellar in Montepulciano for Nobile di Montepulciano, with plenty of free time to explore Pienza and Montepulciano on your own.

What’s missing? Lunch isn’t included, so you’ll want to bring or buy your own meal. Also, some reviews mention that the actual winery visits can feel somewhat commercial, especially at larger venues, which might disappoint if you’re hoping for an intimate, family-owned vineyard experience.

The Itinerary: What You’ll Experience

Starting Point in Siena

The tour kicks off at Piazzale Carlo Rosselli in Siena at 9:30 am. From here, you’ll head into the rolling hills of Tuscany, a drive often praised for its beautiful landscapes—olive groves, vineyards, and cypresses stretching as far as the eye can see.

First Stop: Fattoria Lornano

The first visit is to Fattoria Lornano, where you’ll explore their wine cellar and enjoy a tasting of Chianti. Reviewers who have been there highlight the quality of the wine and the informative tour of the cellar. The one-hour stop is a good chance to learn about local winemaking and sample some authentic Tuscan flavors.

Pienza: The Renaissance Town

Afterward, you’ll arrive in Pienza, a meticulously planned Renaissance town famous for pecorino cheese and its UNESCO World Heritage status. Here, you get about 1 hour and 20 minutes of free time, which many use for a leisurely walk, shopping for cheese and souvenirs, or simply soaking in the views.

Some reviews mention that the views from Pienza are stunning, making it a real highlight—“the gorgeous views and charming streets” are often praised. However, some travelers wish the time in Pienza was longer, or that the visit included more historical insight.

Montepulciano: The Hilltop Gem

Next, the tour moves to Montepulciano, another UNESCO site with ancient streets and panoramic vistas. You’ll have about 1 hour and 45 minutes of free time, giving you a decent window to explore, grab a coffee, or enjoy the atmosphere.

Final Wine Tasting in Montepulciano

The grand finale is a visit to a local winery in Montepulciano for a tasting of Nobile di Montepulciano, one of Italy’s prized wines. Many travelers appreciate this part—reviewers describe it as “a great experience with good wines and snacks,” and some say the guide’s explanations added to the enjoyment.

Return to Siena

By late afternoon, you’ll board the coach for the return trip to Siena, usually arriving around 7 pm.

The Experience: What Travelers Say

Many reviews highlight the expert guides who are friendly, knowledgeable, and often multilingual—”Our guide was incredibly kind and patient, even translating into three languages,” one reviewer noted. The scenic drive gets consistent praise for its beauty, with many describing it as “breathtaking countryside.”

The wine tastings generally receive positive feedback, with some reviewers saying they appreciated the quality of the wines and the chance to taste local specialties in a relaxed setting. One reviewer mentioned, “The wine tasting was very nicely done, and the views in Tuscany are simply beautiful.”

However, not all experiences are flawless. Some travelers point out issues with the transportation—broken seat backs and inadequate shocks—which can make the journey uncomfortable, especially on some of the bumpier roads. Others felt that the winery visits were somewhat commercial or impersonal, especially when visiting larger, more production-oriented wineries.

A recurring concern is that the itinerary isn’t always as advertised. For example, there are multiple reviews where Montalcino was not included—sometimes due to logistical changes or miscommunications. Travelers mention that this can be disappointing if you expected a full wine-focused experience that included multiple towns or vineyards.

Cost-wise, at $147.88 per person, many find this to be reasonable considering the included tastings, transportation, and sightseeing. Still, some wish for more in-depth wine experiences or more time in each town, especially given the price.

Who Should Consider This Tour?

This experience is ideal if you’re looking for a well-organized day trip that combines beautiful scenery, charming towns, and wine tastings without too much hassle. It’s suited for those who enjoy leisurely exploration over deep historical or culture. If you’re traveling with friends or a group who enjoys a social, relaxed vibe, this tour can be a good choice.

On the other hand, if you prefer small, intimate wineries or want a more detailed, guided historical tour of the towns, you might find this tour a bit limited. Also, travelers sensitive to transportation comfort might want to prepare for a potentially bumpy ride, given some of the feedback about the vehicle quality.

Frequently Asked Questions

Is lunch included in this tour?
No, lunch isn’t included. You’ll want to bring a snack or plan to buy something during your free time in Pienza or Montepulciano.

How long is the total tour?
The entire experience lasts about 10 hours and 15 minutes, from departure at 9:30 am until returning to Siena.

What is the group size?
The tour can accommodate up to 50 travelers, so expect a fairly large group, which can affect the intimacy of the experience.

Are the wine tastings in small or large wineries?
The tastings are at established wineries, with some reviews suggesting they can be more commercial or larger-scale, rather than small family-run places.

Can I explore the towns on my own?
Yes. The itinerary includes free time, so you can wander, shop, or relax at your own pace.

Is this tour suitable for families or children?
While not specifically marketed as a family tour, if your kids enjoy scenic drives, wandering picturesque towns, and tasting wine (with appropriate supervision), it could be manageable. However, keep in mind the full-day nature and walking involved.

What language is the tour guided in?
The tour features expert multilingual escorts, and there’s a guarantee of selected languages on certain days. If you’re part of a small group, language options like Portuguese or Chinese may be available.

Is the itinerary fixed?
The tour is confirmed only when the minimum number of participants is reached. Some reviews mention changes, like the removal of Montalcino from the route.

What if the tour is canceled?
You can cancel free of charge up to 24 hours before the experience for a full refund.

How is the transportation provided?
By air-conditioned GT coach or minivan, depending on the number of guests. Some reviews mention issues with vehicle quality, so keep that in mind.

Final Thoughts

If you’re after a relaxed, scenic day out that combines the beauty of Tuscany’s rolling hills with two charming towns and some quality wines, this tour can be a solid choice. Many travelers appreciate the combination of free time, stunning vistas, and knowledgeable guides, making it a good value for the price.

That said, it’s not a highly personalized experience—group sizes can be large, and the winery visits may feel somewhat commercial. It’s best for those who are happy with a flexible, sightseeing-focused day rather than an in-depth wine or history tour.

Ultimately, whether this tour suits your style depends on your priorities: if you want an easy way to see Tuscany’s highlights without much planning and are content with a good, moderate wine tasting experience, it could be just right. But if you’re craving deeper winery visits or more intimate towns, you might want to explore other options.

Happy travels, and may your Tuscan adventure be filled with memorable sights and delicious wines!