From Florence: Montepulciano, Montalcino & Cortona Day Trip

If you’re craving a taste of Tuscany beyond Florence’s historic streets, this full-day guided tour offers a well-rounded peek into the region’s beauty, flavors, and film-famous villages. While we haven’t personally joined the trip, detailed reviews and the tour outline paint a picture of an engaging, culturally rich experience perfect for lovers of wine, history, and authentic scenery.

What we love about this tour? First, it combines three iconic towns—Cortona, Montepulciano, and Montalcino—each offering a unique slice of Tuscany. Second, it features wine tastings in legendary regions, including Nobile di Montepulciano and Brunello di Montalcino—a real highlight for oenophiles. Third, the opportunity to see film locations from Under the Tuscan Sun and The Gladiator adds a touch of cinematic magic.

A possible drawback? The tour’s long day—around 11 hours—means quite a bit of time on the road. While the scenery and experiences are rewarding, those seeking a more relaxed pace might find it a little intense.

All in all, this tour is best suited for curious travelers eager to explore Tuscany’s scenic villages, indulge in wine tastings, and enjoy a well-organized day with expert guides. It’s especially ideal for first-timers looking for a comprehensive taste of the region in one go.

Good To Know

• Comprehensive Day Trip: Covers three major towns—Cortona, Montepulciano, and Montalcino—each offering distinct sights and vibes.
• Cultural & Artistic Experiences: Includes a ceramic demonstration and visits to local artisan shops.
• Wine & Food: Multiple wine tastings, including renowned varieties and an optional light lunch in a historic cellar.
• Scenic Marvels: Passes through UNESCO landscapes of Val d’Orcia, with opportunities for stunning photos at film sites.
• Professional Guides: Led by licensed guides with positive feedback, ensuring a smooth and informative experience.
• Family-Friendly & Practical: Suitable for most travelers, but not wheelchair accessible; dress comfortably and bring a camera.

You can check if your dates are available here:

A Deep Dive into the Experience

Starting Point and Transportation

The adventure begins at Piazzale Montelungo in Florence, where a friendly assistant in blue Caf Tour & Travel gear welcomes you. From there, the journey kicks off with about two hours on a comfortable air-conditioned mini-coach—an excellent way to relax after the morning rush and start soaking in Tuscany’s rolling hills from the window.

The group size is generally manageable, allowing for a friendly atmosphere and easy interaction with guides. The bus timing is well-planned, giving you enough time to settle in without feeling rushed, and the travel is quite scenic, especially as you approach your first stop.

Cortona – The Movie Star Village

Your first stop is the hilltop town of Cortona, famously known from the film Under the Tuscan Sun. This charming medieval village sits high above the countryside, offering panoramic views perfect for photos.

What makes Cortona special? Besides the cinematic fame, it’s a true Etruscan relic. You’ll have about 1.5 hours to wander its narrow streets, explore the quaint shops, and soak in the atmospheric surroundings. A highlight is a ceramic demonstration—or, if unavailable, a visit to artisan shops showcasing traditional crafts. Visitors often comment on how this personal touch adds authenticity to the visit, giving insight into local craftsmanship.

Montepulciano – Renaissance Charm & Wine Royalty

Next, the tour heads to Montepulciano, a medieval town dripping with Renaissance architecture and cinematic history (it appears in New Moon and Medici). Here, you’ll spend around 2 hours and 15 minutes exploring.

The key highlight? The wine tasting experience. You’ll savor five different wines, including the revered Vino Nobile di Montepulciano and a tasting of Brunello di Montalcino, in a historic underground cellar. The tasting is often described as a highlight, especially since it includes fine wines paired with local products, providing an authentic taste of the region’s viniculture.

Many reviewers, like Pierre, appreciated the “professional service” and the enjoyable atmosphere during tastings, noting that the wines are well-selected. Some even take the opportunity to buy bottles directly from the wine shop, with worldwide delivery options available—perfect for wine lovers wanting a keepsake.

A light lunch option is available in a centuries-old cellar—if you choose it—which makes the visit more than just sightseeing; it becomes a culinary experience. If not, you’ll have free time to stroll, shop, or admire the town’s picturesque streets.

More Great Thing To Do Nearby

The Iconic Val d’Orcia Landscape & Film Locations

The drive from Montepulciano takes about 45 minutes through the UNESCO World Heritage Site of Val d’Orcia, a landscape so stunning it’s often used in movies. Expect sweeping views of rolling hills, cypress-lined roads, and idyllic farmhouses.

Photo stops at film locations from The Gladiator add a fun element for movie buffs, and the scenery alone makes this worth the trip. We loved the way these landscapes seem to transport you to another era—an ideal backdrop for reflection or simply capturing memorable photos.

Montalcino – The Wine Fortress

Your final stop is Montalcino, a fortified town famous for its Brunello di Montalcino wine. Spend about 1 hour and 40 minutes here, wandering its historic streets, visiting the fortress ruins, and soaking in the views of the surrounding vineyards.

Wine tasting here is again a focus, with an opportunity to sample Brunello and Rosso di Montalcino. Visitors often remark on the quality of wines and the chance to purchase bottles directly from local shops, with some reviews noting the “delicious food and tapas” that complement the wines.

Montalcino’s medieval charm makes it a fitting finale for a day dedicated to Italy’s wine and history.

Returning to Florence

The journey back takes about 2 hours and 15 minutes, allowing you to relax and reflect on a day packed with culture, scenery, and flavors. The tour concludes back at Piazzale Montelungo in Florence, usually in the late afternoon.

What Makes This Tour Stand Out?

Beyond the picturesque villages and fine wines, this tour offers a rich mix of insights into local artisans, film history, and regional landscapes. The ceramic demo in Cortona, as well as the optional cellar-lunch experience, elevates the visit from a simple sightseeing day to an authentic culture.

The guides, like Leo, receive praise for their professionalism and attentiveness. As one reviewer stated, “His service ensured a successful tour. Very considerate to seniors,” highlighting that the tour is well-organized and inclusive, even if physically demanding at times.

Transportation & Practical Details

The use of air-conditioned mini-coaches means comfort during the long day, and the schedule is structured to maximize sightseeing without feeling overly rushed. The group size tends to be manageable, fostering a friendly atmosphere where questions and interactions are encouraged.

The tour’s price of around $154.52 per person offers good value considering the inclusive wine tastings, ceramic demonstration, and transportation. The flexibility to cancel 24 hours in advance provides peace of mind, especially if your plans change unexpectedly.

Who Should Consider This Tour?

This experience suits travelers eager to explore multiple Tuscan highlights in one day. It’s perfect if you love wine and want to learn about Italy’s most renowned regions through tastings and stories. Also, those with an interest in film locations will find the scenery and stops particularly appealing.

While the tour is generally family-friendly and designed for most able-bodied travelers, it’s not suitable for wheelchair users. Wear comfortable shoes, bring a camera, and prepare for a day that balances sightseeing, tasting, and some walking.

The Sum Up

This tour offers a well-rounded taste of Tuscany, combining charming villages, cinematic landscapes, and legendary wines—all in a manageable, guided format. It’s a fantastic choice for first-time visitors wanting an immersive experience that captures the essence of the region without the need for multiple separate visits.

The inclusion of artisan crafts and the opportunity to purchase wines and local products add a personal touch, making souvenirs more meaningful. The professional guides, especially Leo, ensure a smooth day with plenty of insights, and the scenic drives through UNESCO landscapes are worth the price alone.

If you’re looking for a comprehensive, engaging way to tick off Tuscany’s main attractions in one day, this trip fits the bill perfectly. Lovers of wine, history, and film locations will find it especially rewarding, though even casual travelers will appreciate the stunning scenery and authentic flavors.

FAQ

Is transportation included in the tour?
Yes, the tour includes transport by air-conditioned mini-coach, making the long day comfortable and relaxing.

How long do we spend at each town?
Expect around 1.5 hours in Cortona, 2.25 hours in Montepulciano, and about 1 hour and 40 minutes in Montalcino, plus travel time between stops.

Can I buy wine and local products during the tour?
Absolutely. There’s a chance to purchase wines directly from the shops, with worldwide delivery options available.

Is the tour suitable for families?
It’s generally family-friendly but not wheelchair accessible. Comfortable shoes and a camera are recommended.

What should I bring?
Dress comfortably, wear sunscreen, and bring a camera to capture the stunning views and village scenes.

Is there an option to have lunch included?
Yes, you can opt for a light lunch in a historic underground cellar—if not, there will be free time to explore and find local eateries.

In summary, this day trip from Florence offers a delightful combination of Tuscany’s best—picturesque villages, delicious wines, and cinematic scenery—all guided by friendly experts. It’s perfect for those wanting a comprehensive, enjoyable slice of Italy’s heartland without the hassle of planning each detail.

You can check if your dates are available here: