Small Group Tuscany Tour Montepulciano, Montalcino and Cortona

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Summary
Experience Details
What You’ll Experience
Where to Meet
Reviews
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Duration
11 hours
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Number of Guests
1 - 8 guests
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Language
English
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Digital Ticket
Mobile or paper ticket accepted

Discover Tuscany's treasures with visits to Cortona's workshops, Montepulciano wine tastings, and Montalcino's historic sites. Enjoy scenic vistas and rich flavors on this immersive adventure.

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For each guest that attends this experience, byFood will donate
10 meals

Experience Details

Embark on a captivating journey from Florence to discover Tuscany’s most iconic gems. Begin in Cortona, a hilltop village of Etruscan origin made famous by Under the Tuscan Sun, where you’ll explore medieval charm and visit a master ceramic artisan’s workshop (or traditional artisan shops). Continue to Montepulciano for a tasting of five fine wines, including the prestigious Nobile and Brunello di Montalcino, and enjoy a light lunch in a historic underground cellar (if option selected). Then, travel through the stunning Val d’Orcia, a UNESCO World Heritage Site, with scenic stops including filming locations from The Gladiator. End in Montalcino, a medieval town with a 14th-century fortress and breathtaking views, where you can savor the region’s rich wine culture. Return to Florence with lasting memories of Tuscany’s timeless beauty, history, and flavor.


(*) if not available, it will be replaced with a visit to authentic artisan shops, with typical works


Tour order may vary



What You Get

If option selected: Light Lunch in a unique and exclusive setting, an historic & underground cellar
Opportunity to purchase wines and local products you have enjoyed (worldwide delivery available)
Wine tasting including Vino Nobile di Montepulciano in a historic underground cellar
Hotel pick-up and drop-off

Good To Know

  • (*) if not available, it will be replaced with a visit to authentic artisan shops, with traditional and typical works of the village
  • Travelers should have at least a moderate level of physical fitness
  • Public transportation options are available nearby
  • The tour is confirmed with minimum 4 participants
  • Specialized infant seats are available

What You’ll Experience

1

Cortona

Starting from Florence, the journey takes you to Cortona, one of the most ancient and charming villages in Tuscany. Perched on a hill in the Val di Chiana and made famous by the movie Under the Tuscan Sun, Cortona boasts Etruscan origins, evidenced by the imposing walls surrounding it, which date back to the 4th century BC. The village offers a perfect blend of medieval architecture, authentic atmospheres, and local culture, making it an unmissable destination for those seeking timeless beauty and authenticity.
1 hour 30 minutesAdmission Ticket Free
2

Montepulciano

The next stop is Montepulciano: in this captivating Renaissance town, you’ll have the opportunity to taste the prestigious Nobile di Montepulciano wine in a charming and historic underground cellar, learning the secrets of its production and having the chance to purchase bottles at attractive prices. After the included tasting, you’ll have free time for lunch (not included) at a typical trattoria and to explore the beauties of the historic center, famous as the set for films like New Moon and the series Medici: Masters of Florence featuring Dustin Hoffman and Richard Madden.
2 hoursAdmission Ticket Free
3

Val D'Orcia

As you continue toward the Val d'Orcia, you will enter the heart of one of Tuscany’s most scenic areas, where you can admire the iconic landscapes of rolling hills dotted with cypress trees, known worldwide for their ineffable beauty and recognized as a UNESCO heritage site. Along the way to Montalcino, you will spot the settings of famous films like The Gladiator—a perfect opportunity for taking iconic photos.
20 minutesAdmission Ticket Free
4

Montalcino

The final stop is Montalcino, home to Brunello, one of the world’s most renowned wines. Here, after exploring the quaint historic center, we’ll visit a renowned winery, where you’ll taste Brunello and Rosso di Montalcino wines, immersing yourself in the storytelling of the region’s rich winemaking traditions. Before returning, you’ll have the chance to purchase fine wines directly from the producer—an opportunity not to be missed.
1 hour 40 minutesAdmission Ticket Free

Meeting & Pickup

Meeting Point

Piazzale Montelungo, Firenze Città Metropolitana di Firenze Toscana, Italy, IT

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07:30 am , at Piazzale Montelungo (Montelungo Square), An Assistant waits for you wearing blue clothing with Caf Tour and Gray Line Logos, at the end of the ramp connecting with the railway station.
End Point

This experience ends at the meeting point.

Cancellation Policy

Cancel your booking at least 24 hours before the experience start time to receive a full refund minus a 3.2% transaction fee.

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What People Are Saying
Overall ratings and reviews
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(15)
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We salute you, Leo: great job!
May 23, 2025
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(TripAdvisor)

Leo gave us the most fantastic tour of Tuscany's lovely towns anyone can wish for. His friendly approach endeared him to our group right from the start. His knowledge and love for his country is t...read more

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Tuscany trip
May 23, 2025
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(TripAdvisor)

Great trip. Leo was very knowledgeable. You cannot have a better guide. Would recommend him to all family and friends. We had so much fun.

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Best tour guide
May 21, 2025
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(TripAdvisor)

Our tour guide was the best I’ve ever had. Extremely informative and exceedingly kind/friendly. Leonardo made our Tuscany experience unforgeable. Beautiful country and people! Highly recommend t...read more

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Excellent walk in the Tuscan region with Leandro
May 19, 2025
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(TripAdvisor)

Leandro guided us to the beautiful Tuscan region under a sunny weather! His precious advice and kindness made this experience unforgettable! We recommend with your eyes closed this tour which will ...read more

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Authentic Tuscany
April 02, 2025
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(TripAdvisor)

The tour is well planned and it shows a Tuscany free of mass tourism. Cortona, with the medieval architecture and the ceramic workshop and Montalcino with its fortress were the main highlights. Th...read more

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from  $160.21 
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Please note that the time is in Central European Time.
Free cancellation (24 hours notice)
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from  $160.21  per guest
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Please note that the time is in Central European Time.
Free cancellation (24 hours notice)
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For each guest that attends this experience, byFood will donate
10 meals
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