Tuscany Wine & Hills from Siena - Exploring Pienza: The Renaissance Town

Tuscany Wine & Hills from Siena

Discover Tuscany’s charm on this full-day wine tour from Siena, featuring visits to Pienza and Montepulciano, with wine tastings, scenic views, and free exploration.

The Tuscany Wine & Hills from Siena tour offers a well-balanced combination of scenic beauty, cultural exploration, and wine tasting for $147.88 per person. With a duration of approximately 10 hours and 15 minutes, this tour is designed for those eager to experience the essence of Tuscany without overextending their schedule. It departs from Piazzale Carlo Rosselli in Siena at 9:30 am, making it convenient for visitors staying in or near Siena.

A key strength of this tour is its emphasis on visiting both Pienza and Montepulciano, two of Tuscany’s most celebrated hilltop towns, with ample free time to explore each at a relaxed pace. The inclusion of wine tastings at two renowned wineries adds a flavorful dimension, especially since the stops include Chianti and Nobile di Montepulciano wines. Despite some mixed reviews about vehicle quality and itinerary details, this tour generally suits those interested in combining scenic drives, cultural sights, and wine culture in one day.

Key Points

Tuscany Wine & Hills from Siena - Key Points

  • Full-day tour from Siena covering Pienza and Montepulciano with wine tastings.
  • Visits to local wineries for Chianti and Nobile di Montepulciano wines.
  • Ample free time in both Pienza and Montepulciano for sightseeing and lunch.
  • Transport is by air-conditioned coach or minivan, accommodating up to 50 guests.
  • The tour includes expert multilingual guides and opportunities to purchase local cheeses and wines.
  • Booking is typically done 36 days in advance, with a flexible cancellation policy.

Meeting Point and Transport in Siena

The tour begins at Piazzale Carlo Rosselli in Siena at 9:30 am. Travelers board a comfortable air-conditioned GT coach or minivan. The group size can be up to 50 people, so it maintains a lively yet manageable atmosphere. The transportation is designed to handle the Tuscan roads, although some reviews mention concerns about vehicle comfort, especially on bumpy sections.

Scenic Journey into the Tuscan Hills

Tuscany Wine & Hills from Siena - Scenic Journey into the Tuscan Hills

As the coach winds through Val d’Orcia, the landscape dazzles with olive groves, vineyards, and cypress trees. These views are part of UNESCO World Heritage, making the scenery a highlight of the trip. The coach ride itself sets the tone for the relaxed exploration ahead, with commentary from guides about the region’s geography and culture.

Exploring Pienza: The Renaissance Town

Tuscany Wine & Hills from Siena - Exploring Pienza: The Renaissance Town

Pienza is the first major stop, renowned for its planned Renaissance architecture. The tour allocates about 1 hour and 20 minutes for free time, allowing visitors to stroll its charming streets at their own pace. Many enjoy discovering the local pecorino cheese, which the town is famous for. The walk includes panoramic vistas over the Val d’Orcia, perfect for photos.

Pienza’s Charm and Local Flavors

Tuscany Wine & Hills from Siena - Pienza’s Charm and Local Flavors

During the walk, visitors often appreciate the spacious streets, historic buildings, and scenic overlooks. The free time offers an opportunity for lunch, either at a local café or a small restaurant, though specific options are not included in the tour package. The emphasis remains on enjoying the town’s atmosphere and views.

Montepulciano: The Wine Capital of Tuscany

Tuscany Wine & Hills from Siena - Montepulciano: The Wine Capital of Tuscany

After Pienza, the tour proceeds to Montepulciano, where about 1 hour and 45 minutes are set aside for sightseeing and self-guided exploration. The town’s medieval streets and spectacular views over the surrounding countryside make it a favorite for visitors. Many find the local atmosphere lively, with shops selling wine, cheese, and souvenirs.

Wine Tasting in Montepulciano

Tuscany Wine & Hills from Siena - Wine Tasting in Montepulciano

The highlight here is a visit to a local winery, where the group spends about 1 hour tasting Nobile di Montepulciano, one of Italy’s most esteemed wines. The wine cellar visit allows a close look at traditional winemaking processes, and the tasting is paired with snacks like crackers. Some reviews note the winery is a larger, more commercial operation, which may not satisfy those seeking more intimate, family-owned vineyards.

Additional Wine Experiences and Notable Stops

Tuscany Wine & Hills from Siena - Additional Wine Experiences and Notable Stops

In some cases, the tour includes visits to Fattoria Lornano, where the focus is on Chianti wines. The wine tasting here lasts about an hour and includes a visit to the cellar. The scenery surrounding the wineries enhances the tasting experience, with views of vineyards and rolling hills.

The Freedom to Explore Each Village

Tuscany Wine & Hills from Siena - The Freedom to Explore Each Village

Both Pienza and Montepulciano are provided with free time, usually around 1 hour in Pienza and 1 hour and 45 minutes in Montepulciano. This allows for independent exploration—visiting shops, enjoying optional meals, or simply soaking in the views. The tour’s pacing seems well-planned for those who prefer self-guided discovery rather than a rigid schedule.

Practicalities and Customer Feedback

Included in the price are transportation, expert guides, wine tastings, and snacks. Lunch is not included, giving flexibility for personal preferences or local dining options. While most reviews highlight friendly guides and beautiful scenery, some point out vehicle concerns and discrepancies in the itinerary, such as the removal of certain stops like Montalcino.

A few reviews mention larger group sizes or less personalized experiences, but generally, the guided commentary and scenic drives compensate for this. The tour is confirmed only when the minimum number of participants is reached, and free cancellation is available up to 24 hours before.

Who Will Appreciate This Tour Most?

This tour appeals to wine enthusiasts, with its focus on tasting Chianti and Nobile di Montepulciano. It’s also suitable for those who value free time in charming towns for self-guided exploration. Travelers preferring small, intimate visits might find the larger winery stops less appealing, but overall, the experience delivers beautiful landscapes, cultural sights, and local wines.

Final Thoughts on the Tuscany Wine & Hills Tour

The full-day itinerary balances scenic drives, cultural sightseeing, and wine tasting in a way that works well for many visitors. The scenic landscapes of Val d’Orcia and the delightful towns of Pienza and Montepulciano stand out as core attractions. The guided wine tastings provide a taste of Tuscan winemaking tradition without the need for multiple separate excursions.

While some reviews note vehicle comfort issues and itinerary changes, the overall experience remains positive, especially considering the value for money and the quality of the scenery. This tour is best suited for those looking to combine wine, culture, and countryside in one seamless day.

Ready to Book?

Tuscany Wine & Hills from Siena



4.0

(96)

“We had a very knowledgeable tour guide and great driver. The wine tours were great as well as the two cities that we visited.”

— Benjamin M, Mar 2025

Frequently Asked Questions

Does this tour include lunch?
No, lunch is not included, allowing flexibility to dine at your own pace during free time in Pienza or Montepulciano.

What wines are tasted during the tour?
The tour features Chianti at Fattoria Lornano and Nobile di Montepulciano at a winery in Montepulciano.

Is transportation comfortable?
Most guests find the air-conditioned coach or minivan suitable, but some reviews mention concerns about vehicle quality during certain sections.

Can I explore the towns on my own?
Yes, ample free time in both Pienza and Montepulciano allows for self-guided exploration and casual sightseeing.

What is the cancellation policy?
Guests can cancel free of charge up to 24 hours before the tour start time for a full refund.

Who is this tour ideal for?
It suits wine lovers, cultural explorers, and those wanting scenic views with flexible sightseeing time in Tuscany’s iconic towns.