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Discover Tuscany’s highlights with this small-group day trip from Florence, including Cortona, Montepulciano, Montalcino, wine tastings, and artisan ceramics.

This 11-hour small-group day trip from Florence offers a comprehensive taste of central Tuscany’s most captivating towns. For an accessible price, travelers get to explore Cortona, Montepulciano, and Montalcino, renowned for their beauty and world-class wines. The tour includes five wine tastings, a ceramic workshop, and scenic views of the UNESCO World Heritage landscape of Val d’Orcia. An optional light lunch inside a historic underground wine cellar adds a delightful culinary touch. The tour caters to those interested in art, wine, and authentic Tuscan scenery, with a friendly, professional guide leading the way.
While the itinerary is packed and the distances between towns are covered comfortably by coach, it’s worth noting that wheelchair users are not suitable for this experience. The tour’s pacing is tailored to be considerate, especially for senior participants, ensuring everyone can enjoy the stops comfortably.
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The tour departs from Piazzale Montelungo, easily accessible at the end of the ramp connecting with the Florence railway station. An assistant wearing blue clothing with Caf Tour & Travel – Gray Line logos welcomes you, ensuring a smooth start. The journey is conducted by coach, with two hours of travel from Florence to Cortona, setting the tone for a comfortable and scenic drive through Tuscany’s rolling countryside.

Cortona is the first major stop, known for its medieval streets and Etruscan walls that tell stories of ancient civilizations. The visit includes a photo stop, sightseeing, and free time to explore the town’s narrow alleys. This charming hilltop village exudes a timeless atmosphere, perfect for soaking in panoramic vistas or browsing local shops.
A highlight here is the artisan ceramic workshop. Visitors gain exclusive access to see traditional hand-painting techniques passed down through generations. If the ceramic workshop isn’t available, the group visits authentic artisan shops instead, showcasing traditional Tuscan works.

After Cortona, the coach travels roughly 50 minutes to Montepulciano. This town is famous for its Renaissance architecture and prestigious Vino Nobile. The guided visit allows free time to walk through medieval streets, admire Renaissance palaces, and shop for local products.
The highlight in Montepulciano is the wine tasting inside a historic cellar. Here, you’ll sample five Tuscan wines, including Vino Nobile and Brunello di Montalcino, known worldwide for their quality. The guided tasting provides insights into the wines’ history and production, making it enjoyable for both wine enthusiasts and casual sippers.
If the light lunch option is selected, it takes place inside the underground wine cellar, where centuries-old stone vaults create a cozy atmosphere. This Tuscan-style meal complements the wine tasting experience and offers a chance to relax amid historic surroundings.
More Great Tours NearbyThe tour continues with a scenic drive through the Val d’Orcia, a landscape recognized by UNESCO for its beautiful rolling hills, medieval farms, and iconic cypress-lined roads. This area provides some of the most photographed views in Tuscany and offers a perfect backdrop for memorable photos during the journey.

The final stop is Montalcino, a medieval village crowned by an imposing fortress. This town is celebrated for its Brunello wines, considered among the best in Italy. Visitors have free time to wander the cobbled streets, explore local shops, and admire panoramic views of the surrounding countryside.
The visit includes another wine tasting, offering a chance to sample more Brunello and learn about its production. The town’s medieval charm and spectacular vistas make it a fitting finale for the day trip.

After spending about 100 minutes in Montalcino, the coach begins the return trip to Florence, covering a 2 hours and 15 minutes drive. The tour concludes back at Piazzale Montelungo, ensuring easy access for travelers to continue their day or return to accommodations.

The tour offers free cancellation up to 24 hours in advance, giving flexible planning options. Travelers can reserve now and pay later, making it simple to secure a spot without immediate payment. The experience is guided by an English-speaking guide, with a minimum of 4 participants required for confirmation.

This day trip suits those eager to see multiple Tuscan towns within a manageable day, especially if they enjoy wine tasting and artisan crafts. It’s perfect for travelers who appreciate scenic views, historical sites, and local food and drink. The tour’s pacing and inclusive stops make it accessible for most, though wheelchair users are not suited for this experience.
This tour offers a well-rounded introduction to Tuscany’s highlights, combining culture, scenery, and wine in an accessible format. The presence of five wine tastings and an artisan ceramic experience adds a touch of authenticity that appeals to many travelers.
The professional guides earn praise for their attentiveness and knowledge, with Lorenzo and Leo noted for their personable service. The option to include a light Tuscan lunch enhances the experience for those wanting a more relaxed and flavorful day.
While the itinerary is quite full, it’s designed to give a comprehensive taste of Tuscany’s best in just over half a day of travel. The overall rating of 5 out of 5, based on positive reviews, reflects its reputation as a popular and reliable choice for visitors eager to explore Tuscany’s timeless towns and wines.
Is the tour suitable for children or seniors?
The tour is designed to be considerate of senior participants, with pacing adjusted accordingly. However, wheelchair users are not suitable due to the nature of the stops and walking involved.
What should I bring on the tour?
Travelers should wear comfortable shoes, carry a camera for photos, and bring sunscreen for sunny days. The journey involves scenic drives and walking through towns, so comfort is key.
Can I cancel if my plans change?
Yes, the tour allows free cancellation up to 24 hours in advance for a full refund, providing flexibility in planning.
How many wine tastings are included?
You will enjoy tasting five different Tuscan wines, including Vino Nobile and Brunello, in historic cellars and wine shops.
What is the significance of the artisan ceramic workshop?
The workshop offers exclusive access to see traditional hand-painting techniques, showcasing Tuscany’s artisan craftsmanship. If unavailable, authentic artisan shops are visited instead.