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Explore Tuscany’s highlights in a private day trip from Florence to Montepulciano and Siena, including hilltop views, medieval squares, and Gothic cathedral.
Discover Tuscany’s timeless charm on this private day trip from Florence that takes you to Montepulciano and Siena. For $449.43 per person, this approximately 7 to 8-hour tour offers a comfortable, air-conditioned vehicle, private transfers, and flexible scheduling. The tour is perfect for those who want an intimate experience of Tuscany’s historic towns without the hassle of driving or navigation. With group discounts available and pickup included, it’s designed to make your day smooth and memorable. The tour’s reviews highlight friendly drivers and stunning views, making it a reliable choice for travelers seeking a curated, personal exploration of this beautiful region.
While the admission tickets for attractions like the Siena Cathedral are not included, the beautiful towns and panoramic vistas more than compensate. The driver shares knowledge about the region, adding depth to the experience, although he is not a licensed guide. This tour offers a balance of relaxed exploration and local insight, making it ideal for visitors who value comfort and authenticity.


This tour departs from Florence with a private air-conditioned vehicle, allowing for a hassle-free journey through the Tuscan countryside. The pickup service ensures a smooth start to the day, and you’ll get to enjoy the scenic drive through rolling hills and vineyards en route to Montepulciano.
The timing allows for approximately 2 hours in each town, giving enough time to walk through the streets, admire the architecture, and take in the views. The driver shares insights about the towns’ history and highlights, making the drive as informative as it is scenic.
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Montepulciano is renowned for its Medici-era architecture and Vino Nobile di Montepulciano wine. The main square, Piazza Grande, is a highlight, with its elegant buildings and lively atmosphere. Travelers can visit the Torre di Pulcinella, a tower offering sweeping panoramic views of the Tuscan landscape. This stop provides a free opportunity to capture stunning photos and get a sense of the town’s historic grandeur.
The 2-hour visit is enough to explore the historic center at a relaxed pace, with options to browse local shops or enjoy a quick coffee. The admission to the tower is free, but it’s wise to check opening hours if planning to climb.

In Siena, the Piazza del Campo takes center stage as one of Europe’s most impressive medieval squares. The Palazzo Pubblico and Torre del Mangia enhance the square’s skyline, offering a glimpse into Siena’s civic history. The Siena Cathedral, a jewel of Italian Gothic architecture, is a must-see. Visitors can climb to the top of the cathedral tower for extraordinary views over Siena and its surroundings.
The 2-hour stop here is ample to soak in the atmosphere, explore the cathedral interior, and take photos from the tower. The tickets for the cathedral and tower are not included but can be purchased on-site or online.

This tour’s private vehicle is described as clean and comfortable, with bottled water provided. The friendly driver shares regional knowledge and offers extra time at stops, which adds flexibility to the schedule. While he is not a licensed guide, his local insights help enrich the experience.
The pickup and drop-off service simplifies logistics, especially for those unfamiliar with Florence’s transport options. The customer care available 24/7 provides support before and after booking, adding reassurance.

Admission tickets for Siena’s cathedral and tower are not included in the tour price, so travelers should plan to purchase these separately if interested. Meals and refreshments are also not covered, so packing a snack or planning for meals during the day is advisable.
The tour runs daily, with operating hours from 12:00 AM to 11:30 PM, offering flexibility for booking. Travelers are advised to verify opening hours and ticket availability ahead of time to avoid surprises.
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This private experience suits those who prefer a relaxed pace and personalized service over large group tours. It’s ideal for visitors who want to see two of Tuscany’s most iconic towns with minimal stress, in a comfortable setting. The scenic drive, stunning views, and cultural highlights make it especially appealing for first-time visitors or those short on time but eager to explore.
While it offers flexibility and insider insights, it’s worth noting that the driver is not a licensed guide. Those seeking more in-depth guided tours might prefer additional guided options or tours with included admission tickets.

This private day trip from Florence provides a convenient, comfortable way to see Montepulciano and Siena in one day. The timed stops at each town allow visitors to enjoy the highlighted sights and views without feeling rushed, thanks to the flexible driver and private transfer.
The main attractions, like Piazza Grande, the Torre di Pulcinella, and the Siena Cathedral, are complemented by the scenic drive through Tuscany’s famous countryside. The friendly driver’s local insights add a layer of authenticity, making this tour a good fit for those who value comfort and personalized service.
However, travelers should plan ahead to purchase tickets separately for certain sites, and those wanting a guided experience with detailed histories might want to explore other options. Nonetheless, for easy access to Tuscany’s most beautiful towns, this tour offers value, convenience, and stunning scenery.
“Very friendly, excellent driving skills, gave us extra time at places, and was flexible. We would definitely recommend to anyone looking for a driver.”

Is transportation included in the tour?
Yes, private transfers in an air-conditioned vehicle are included both ways, making the journey comfortable and stress-free.
Are tickets for Siena’s cathedral included?
No, admission tickets are not included. Visitors should purchase tickets to the Siena Cathedral and tower separately or on the day of the visit.
How long do stops last in Montepulciano and Siena?
Each stop lasts approximately 2 hours, providing enough time for sightseeing, photos, and brief exploration.
Is this tour suitable for all ages and physical abilities?
Most travelers can participate, with most travelers able to participate. The stops involve walking through towns and climbing towers, so some mobility is needed.
Can I get extra time at specific sights?
Yes, the driver is described as flexible and willing to give extra time at stops, depending on your preferences.
What should I bring for this tour?
Bring comfortable shoes, some cash or cards for site tickets and snacks, and plans for meals since food and drinks are not included.
Is the tour available year-round?
Yes, the tour operates daily from April 29, 2025, through May 18, 2026, with flexible hours.
How far in advance should I book?
On average, this tour is booked 90 days in advance, so early reservation is recommended to secure your preferred date.