Private tour from Florence to CORTONA & MONTEPULCIANO

Exploring Tuscany: A Private Day Trip to Cortona & Montepulciano from Florence

If you’re looking to see some of Tuscany’s most picturesque hill towns without the hassle of public transportation or crowded tours, this private tour from Florence hits the sweet spot. Priced at around $426.39 per person, it offers roughly 10 hours of personalized exploration, including visits to the famously cinematic Cortona and the beautifully preserved Montepulciano. Led by friendly, knowledgeable guides like Massimo, this experience combines comfort, flexibility, and authentic charm.

What we really love about this tour is the luxury of private transport in a plush Mercedes-Benz V Class, which makes the trip both relaxed and stylish. Plus, the fact that your guide suggests the best spots to stop and takes into account your interests means you get a truly customized day out. The scenic drive through the Arno Valley and the stunning views from hilltop towns are enough to make any photographer smile. On the downside, this tour doesn’t include lunch—so you might want to plan for that—yet the optional add-on of a winery visit can turn this into a complete sensory experience.

This tour is perfect for those who want to combine sightseeing with comfort and prefer a tailored experience over rigid group schedules. Whether you’re a history lover, a wine enthusiast, or just someone who appreciates the charm of small towns, you’ll find plenty to love here.

Key Points

• Personalized Experience: A private guide ensures you explore based on your interests, not a preset schedule.
• Comfort & Style: Travel in a luxurious Mercedes-Benz with WiFi and climate control, making the day smooth and enjoyable.
• Cultural & Movie Connection: Cortona’s claim to fame as the setting for Under the Tuscan Sun offers a charming backdrop.
• Scenic Drive & Views: The journey offers breathtaking panoramas of the Tuscan countryside and Lake Trasimeno.
• Wine & Food Options: Optional visits to top-rated wineries and tastings enhance the experience.
• Flexible & Customizable: Your guide can pause for photos or extra stops, making this a truly tailored trip.

A Detailed Look at This Tuscany Day Trip

Starting Point & Comfort

The tour begins early, with a pickup from your Florence hotel in a luxurious Mercedes-Benz V Class, a big plus for those tired of cramped buses. The comfort and privacy are immediately noticeable, and the ride sets a relaxed tone. With air conditioning and WiFi onboard, you can chat with your guide, catch up on some photos, or just enjoy the scenery.

First Stop: Cortona and the Duomo di Cortona

Within about an hour and a half, you’ll arrive at Cortona, perched about 600 meters above sea level. The town’s stone walls and medieval charm instantly evoke a sense of stepping back in time. You’ll visit the Duomo di Cortona, and from its elevated position, you’ll enjoy spectacular views of the surrounding valley and Lake Trasimeno.

What makes Cortona a standout is its fame from the book and movie Under the Tuscan Sun. Many visitors comment on how it’s easy to fall in love with the town, its friendly people, and the relaxed atmosphere. One reviewer notes how their guide, Massimo, made the visit enjoyable by filling the time with interesting tidbits, ensuring they had ample opportunity to explore at their own pace.

Mid-Morning: Exploring & Photos

While the tour is flexible, our favorite part is the unhurried exploration of Cortona’s alleys, piazzas, and historic sites. You’ll have around 1.5 hours here, enough to soak in the atmosphere, browse local shops, or sit for a coffee. The guide’s local knowledge makes sure you see the best spots for photos and insider tips.

Lunch & Wine Tasting at a Family Winery

Around 11:30 am, you’ll head to a family-run winery for a light lunch—a perfect way to fuel up for the afternoon. While the tour price doesn’t include lunch, this stop is often praised for its delicious local fare and the chance to enjoy authentic Tuscan flavors.

If you opt for the wine tasting add-on, you’ll get to sample some of the region’s renowned Nobile wines. Several reviews highlight how the wine tasting experience was a major highlight, with visitors praising the quality of wines and the chance to learn about local production methods. One guest mentioned, “the wine and food was amazing,” and appreciated the personalized attention.

The Drive to Montepulciano & Piazza Grande

Post-lunch, your driver takes you on a relaxing 30-minute drive through rolling hills dotted with vineyards and olive groves. Stop anytime for photos—your guide is happy to accommodate spontaneous requests. As you arrive in Montepulciano around 2 pm, you’ll be greeted by another stunning medieval town.

Montepulciano: The Jewel of Tuscany

This hilltop town is famous for its Renaissance architecture and Vino Nobile, Italy’s historic red wine. The town’s charming squares, elegant palaces, and hidden alleyways invite gentle exploration. Visitors love walking through its medieval streets, soaking up the authentic atmosphere, and discovering small artisan shops.

Reviews mention how Alessandro, the guide, made the experience especially memorable, sharing insights into the town’s history and local culture. One reviewer called Montepulciano “completely charming,” noting that the town’s beauty is best appreciated at a leisurely pace.

Final Hours & Optional Activities

With around two hours in Montepulciano, you have time to visit the Piazza Grande, admire the cathedral, or browse local markets. If wine tasting was not part of the original plan, you might consider visiting a top-rated vineyard on your own or with your guide.

What Travelers Say

Reviewers consistently praise the knowledgeable guides who bring Tuscany’s stories alive, making the experience informative and fun. Robyn from her review states, “Massimo knew how to fill our time and gave us plenty of spare time to explore,” highlighting the flexibility and personalized touch.

Many mention the stunning scenery, with one noting, “the views from the hill towns are simply breathtaking,” and another emphasizing the quality of the wine and delicious local food. The comfortable transportation and smooth logistics also receive high marks, allowing you to relax and enjoy the day without worries.

Practical Details & Considerations

This tour is designed as a private experience, meaning only your group will participate—perfect for couples, families, or friends seeking exclusivity. The pick-up and drop-off at your Florence accommodation make it very convenient, especially if you’re staying outside the city center.

The price point might seem high, but considering the luxury transport, private guide, and tailored experience, it offers excellent value for those wanting an authentic, hassle-free day in Tuscany. The optional winery visit can add a memorable tasting experience, making this an excellent choice for wine lovers.

What to Wear & Bring

Casual, comfortable shoes are recommended, as both towns involve some walking on cobblestone streets. Dress casually—Tuscany’s weather can vary, so check the forecast. You might also want to bring a camera, sun protection, and a small backpack for your personal items.

Booking & Cancellation

The tour is popular, booked roughly 74 days in advance on average, indicating high demand. Cancellation is free up to 24 hours before, offering flexibility if your plans change.

Who Would Love This Tour?

This private day trip suits travelers who value comfort, customization, and authentic experiences. If you’re interested in stunning views, medieval towns, and local wines, you’ll find this tour a perfect fit. It’s especially good for those wanting a luxurious yet relaxed way to experience Tuscany’s highlights without feeling rushed.

The Sum Up

This private tour from Florence to Cortona and Montepulciano offers a thoughtfully curated, comfortable way to see some of Tuscany’s most enchanting towns. It’s ideal for those seeking a personalized experience, with the flexibility to explore at your own pace, enjoy spectacular scenery, and sample regional wines and foods. The knowledgeable guides and luxury transportation elevate the experience beyond a typical group tour, making it well worth the price for those who want a special, hassle-free day in Italy’s heartland.

Whether you’re a history buff, a wine connoisseur, or simply someone who appreciates the beauty of small towns, this trip offers a memorable taste of Tuscany. It’s a chance to see iconic locations, enjoy breathtaking views, and savor authentic flavors—all in one seamless, private day out.

FAQ

How long is the tour?
The tour lasts approximately 10 hours, starting around 8:30 am and concluding with drop-off back at your Florence accommodation.

What is included in the price?
The cost covers hotel pickup and drop-off, private driver/guide, transport in a luxury Mercedes-Benz V Class with WiFi, and all taxes, tolls, and parking fees. Lunch is not included but is available at a local winery with an optional tasting.

Can I add a winery visit?
Yes, you can opt to include a visit to a top-rated winery for an additional expense. This is recommended for wine lovers who want to taste some of Tuscany’s finest.

What should I wear?
Casual attire and comfortable shoes are advised, as you’ll be walking through cobblestone streets and historic sites.

Is this tour suitable for all travelers?
Most travelers can participate, especially since it’s a private experience. However, those with mobility issues should consider walking distances and cobblestone terrain.

How far in advance should I book?
The tour is typically booked about 74 days ahead, so planning early ensures availability, especially during peak seasons.

What happens if I need to cancel?
You can cancel free of charge up to 24 hours before the tour starts, receiving a full refund.

Can I customize this tour?
Absolutely. The guide will suggest the best stops based on your interests, and the schedule can be adjusted to include additional activities like wine tastings or extra sightseeing.

Is there a dress code?
Casual, comfortable clothing is fine. Dress appropriately for walking and the weather conditions.

This private day trip to Cortona and Montepulciano offers an engaging, flexible way to experience Tuscany’s timeless beauty with comfort and personalized service. Whether you’re seeking iconic sights, scenic drives, or regional wines, it’s a memorable journey through Italy’s heartland.