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Explore Tuscany with a full-day tour from Florence visiting Monteriggioni, Montalcino, and Pienza, including optional wine tasting and medieval sights.

This 11-hour tour offers a memorable journey through some of Tuscany’s most iconic medieval villages and landscapes. For just $62.63 per person, travelers explore Monteriggioni, known for its ancient walls and Templar legend, Montalcino with its renowned wines, and Pienza, famous for its cheese. The tour includes guided visits, free time, and the option to indulge in wine and local produce tasting in Montalcino.
Departing from Florence’s Santa Maria Novella train station, this guided trip is perfect for those eager to experience Tuscany’s historic charm and stunning scenery in a single day. With air-conditioned transport and multilingual guides, it balances sightseeing and relaxation. While the tour’s pace is lively, some stops offer extensive free time to explore at your own pace.
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The tour begins at the Sightseeing Experience Visitor Center near Florence’s Santa Maria Novella station. From there, travelers board a comfortable air-conditioned GT bus equipped with Wi-Fi, setting the tone for a smooth, scenic ride through Tuscany’s rolling hills.
The first major stop is Monteriggioni, a small fortified village with walls dating back to 1200 AD. Visitors get approximately 80 minutes for a photo stop, a visit to the medieval walls, and some free time to walk the charming streets. The walls and historic atmosphere make it a favorite for lovers of medieval architecture. During the walk, the impressive fortifications are tangible reminders of Tuscany’s turbulent past.

Included in the tour is a visit to the Templar Museum, which takes about 20 minutes. This museum is dedicated to the Knights Templar, and visitors can marvel at various artefacts that tell stories of the legendary order. The museum’s story, linked to Monteriggioni’s walls, adds an intriguing layer of history to the visit, blending legend with real relics.
While not included in the “Transfer Only” option, the museum visit enriches the experience for those interested in medieval legends and the Templar presence in Tuscany. Travelers generally find the museum informative and an engaging part of the overall tour.

After Monteriggioni, the journey continues into the Val d’Orcia, a UNESCO site celebrated for its scenic emerald hills and golden fields. The next stop is Montalcino, a hilltop town renowned worldwide for its Brunello di Montalcino wine.
Guests are given about 2.5 hours to explore Montalcino’s narrow streets, authentic shops, and historic sites. This free time allows for a leisurely stroll and some window shopping. The highlight for many is an optional wine tasting, which can include Brunello di Montalcino, Rosso di Montalcino, and local produce like cold cuts and cheeses.
This tasting experience has received high praise for its value, providing a chance to sample some of Tuscany’s best wines paired with regional delicacies in a relaxed setting. The town offers fabulous panoramic views of the surrounding countryside, perfect for photography and soaking up the atmosphere.
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The final stop is Pienza, celebrated for its cheese production, particularly Pecorino di Pienza. Visitors have about 1.5 hours of free time here, ideal for shopping at local cheese shops or simply wandering the picturesque streets.
The town’s Fabulous panoramic views over the Val d’Orcia make it a perfect place to relax and take photos before heading back to Florence. The historic center is small but charming, offering authentic artisan shops and a sense of rural Tuscany life.
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The tour departs from the Sightseeing Experience Visitor Center at Florence’s Santa Maria Novella station, with a strict policy on punctuality. The bus is equipped with Wi-Fi and air conditioning, making the long day comfortable. Guides speak Spanish, English, and Portuguese, guiding travelers through each location with detailed commentary.
Included in the price are entry to the walls of Monteriggioni and the Templar Museum, plus the wine and local produce tasting in Montalcino if the option is selected. Meals are not included, and hotel pickup or drop-off is not provided, making this tour ideal for those who prefer organized transportation and guided visits.

Travelers seeking independence can opt for the “Transfer Only” package, which includes just the bus service and assistance onboard. This allows for more personalized exploration in Monteriggioni, Montalcino, and Pienza, but without guided visits or included entries.
This option suits travelers who prefer to wander at their own pace or who want to focus on specific towns without the structured itinerary.

The positive reviews highlight knowledgeable guides, stunning scenery, and well-organized logistics. Guides like Anna, Juliano, Ilaria, Vanessa, and others are praised for their welcoming nature and insightful commentary. The scenery of Tuscany’s rolling hills and historic towns impresses consistently, with many reviewers noting incredible views during the drive and at each stop.
The wine tasting in Montalcino is a highlight, offering a value-packed experience of Tuscan wines paired with local cold cuts and cheeses. The small group size and efficient pacing contribute to a satisfying, unhurried feeling during the day.

This full-day experience is well-suited for travelers who want a rundown of Tuscany’s medieval towns and landscapes without the stress of planning. The guided visits and free time combine to create a balanced experience catering to history lovers, wine enthusiasts, and those seeking scenic relaxation.
However, travelers seeking culinary experiences might prefer a tour with a longer or more specialized wine tasting or food stops. Also, those with mobility issues should consider walking distances and the time spent exploring the towns’ historic centers.
This Monteriggioni & Val d’Orcia tour offers a rich combination of history, scenery, and regional flavors for a fair price. The inclusion of guided visits and the chance to tast real Tuscan wines makes it a compelling choice for anyone wanting a taste of Tuscany in a single day.
While the pace can be brisk, the expert guides, comfort on the bus, and beautiful stops ensure a memorable experience. It’s especially appealing for those who appreciate medieval architecture, picturesque landscapes, and local food and wine.
This tour provides excellent value for a full day of sightseeing, and the high ratings reflect broad satisfaction among past participants. It’s a practical, enjoyable way to see Tuscany’s highlights without the hassle of driving or extensive planning.
“Great experience to see a good representation of the Tuscany area. The three towns we visited were interesting and had beautiful views of the count…”
What is included in the tour?
The tour includes bus transportation, Wi-Fi onboard, guides speaking Spanish, English, and Portuguese, entry to Monteriggioni walls, Templar Museum visit, and wine and produce tasting in Montalcino if selected.
How long is the tour?
The total duration is 11 hours, with specific stops at Monteriggioni, Montalcino, and Pienza, along with free time at each location.
Where does the tour start and end?
It begins at the Sightseeing Experience Visitor Center near Florence’s Santa Maria Novella train station and ends back there at the conclusion of the day.
Is the wine tasting included?
The wine and local produce tasting is included if the option is selected, featuring Brunello di Montalcino, Rosso di Montalcino, cold cuts, and cheeses.
Can I explore the towns independently?
Yes, the “Transfer Only” option allows for independent visits to each village without guided tours or entries.
Is meals included?
No, meals are not included in the tour price, giving flexibility for personal dining choices.
What guides will I have?
Guides speak English, Spanish, and Portuguese, but not the “Transfer Only” option does not include a guide.
Is this tour suitable for all mobility levels?
The tour involves walking on medieval streets, so travelers with mobility issues should consider the walking distances at each stop.
What makes this tour different from other Tuscany day trips?
Its combination of historic sites, scenic views, and optional wine tasting in Montalcino, plus the well-rated guides and small group experience, set it apart.
How do I book with flexibility?
You can reserve now and pay later or cancel up to 24 hours in advance for a full refund, offering peace of mind in planning.
Is there a particular time of year best for this tour?
While not specified, the scenery and outdoor walking are generally best during spring or fall when weather is mild, but the tour runs year-round subject to availability.