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5 Days of Wine and History in Tuscany

5 Days of Wine and History in Tuscany Itinerary

Last updated: 2024 Jun 29

Exploring Montalcino's Rich Heritage

Morning
Start your Tuscan adventure with a visit to Montalcino. This charming hill town is renowned for its Brunello wine and offers stunning views of the surrounding countryside. Stroll through its medieval streets, taking in the historic architecture and vibrant local culture.
Afternoon
In the afternoon, delve deeper into Montalcino's history with a tour of Montalcino Fortress (Fortezza di Montalcino). This imposing fortress dates back to the 14th century and provides panoramic views of the Val d'Orcia. Explore its well-preserved ramparts and learn about its strategic importance in Tuscan history.
Evening
Conclude your day with a delightful wine tasting experience at Montalcino: Walk of Wine Tour with Vertical Brunello Tasting. This tour offers an in-depth look at the production of Brunello di Montalcino, one of Italy's most prestigious wines. Enjoy a guided tasting session that includes multiple vintages, paired with local delicacies.
Bedtime
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Visit Montalcino in Montalcino
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Montalcino

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Visit Montalcino Fortress (Fortezza di Montalcino) in Montalcino
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Montalcino Fortress (Fortezza di Montalcino)

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Val d'Orcia Adventures and Delights

Morning
Begin your second day with an exhilarating Val d'Orcia: Private Photography Safari Tour with Aperitif. Capture the breathtaking landscapes of Val d'Orcia, a UNESCO World Heritage site, under the guidance of a professional photographer. The tour concludes with a refreshing aperitif amidst the picturesque scenery.
Afternoon
After your photography safari, embark on an unforgettable culinary journey with Val D'Orcia: Private Olive Oil Tasting and Tuscan Dinner. Learn about the traditional methods of olive oil production and savor a delicious Tuscan dinner featuring locally sourced ingredients.
Evening
As evening falls, unwind with Val d'Orcia: Magical 3-Course Dinner under the Oak Tree. This enchanting dining experience takes place under a centuries-old oak tree, offering a magical ambiance as you enjoy a gourmet meal paired with fine wines from the region.
Bedtime
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Visit Val d'Orcia Private Photography Safari Tour with Aperitif in Val d'Orcia
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Val d'Orcia: Private Photography Safari Tour with Aperitif

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Visit Val D'Orcia Private Olive Oil Tasting and Tuscan Dinner in Val d'Orcia
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Val D'Orcia: Private Olive Oil Tasting and Tuscan Dinner

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Historical Treasures and Culinary Experiences in Pienza

Morning
Kick off your third day by exploring Pienza, often referred to as the 'Ideal City' due to its Renaissance architecture. Visit Pienza: Palazzo Piccolomini & Palazzo Borgia Entrance Ticket to admire these historic palaces that showcase exquisite art and design from the 15th century.
Afternoon
In the afternoon, immerse yourself in local traditions with Pienza: Dairy Farm Tour with Pecorino Cheese Tasting. Discover how Pecorino cheese is made on this family-run farm and enjoy tastings of various cheese varieties while learning about their unique flavors.
Evening
Wrap up your day in Pienza by participating in Pienza: Dining Experience at a Local's Home. This intimate dining experience allows you to savor authentic Tuscan dishes prepared by locals in their own home. It's a perfect way to end your day immersed in genuine Italian hospitality.
Bedtime
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Visit Pienza: Palazzo Piccolomini & Palazzo Borgia Entrance Ticket in Pienza
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Pienza: Palazzo Piccolomini & Palazzo Borgia Entrance Ticket

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Visit Pienza Dairy Farm Tour with Pecorino Cheese Tasting in Pienza
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Pienza: Dairy Farm Tour with Pecorino Cheese Tasting

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Truffle Hunting and Wine Tasting in Trequanda

Morning
Start your day with an exciting Trequanda: Tuscan Truffle Hunting Experience with Lunch. Join expert truffle hunters and their dogs as you search for these prized delicacies in the picturesque woods of Trequanda. After the hunt, enjoy a sumptuous lunch featuring freshly harvested truffles, paired with local wines.
Afternoon
After your truffle adventure, head to a nearby vineyard for Montalcino: Private Cellar Tour, Wine Tasting & Appetizers. This private tour offers an exclusive look at the winemaking process, from grape to glass. Sample a selection of fine wines accompanied by delicious appetizers, all while taking in the beautiful vineyard scenery.
Evening
Conclude your day with a relaxing evening at Aperitif on the Terrace of Podere Montale at Sunset. Enjoy stunning views of the Tuscan countryside as you sip on refreshing aperitifs and savor light bites. The serene ambiance and breathtaking sunset make for a perfect end to your day.
Bedtime
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Visit Trequanda Tuscan Truffle Hunting Experience with Lunch in Trequanda
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Trequanda: Tuscan Truffle Hunting Experience with Lunch

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Visit Montalcino Private Cellar Tour, Wine Tasting & Appetizers in Trequanda
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Montalcino: Private Cellar Tour, Wine Tasting & Appetizers

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E-Bike Adventure and Cooking Class in Pienza

Morning
Begin your final day with an invigorating Pienza: Guided E-bike Tour through the Val d'Orcia. Explore the rolling hills and scenic landscapes of Val d'Orcia on an electric bike, guided by a knowledgeable local. This eco-friendly tour allows you to cover more ground while enjoying the fresh air and stunning views.
Afternoon
After your e-bike adventure, immerse yourself in Tuscan culinary traditions with Cooking Class in a Brunello Winery - Private experience. Learn how to prepare classic Tuscan dishes using fresh, local ingredients under the guidance of an experienced chef. The class takes place in a beautiful Brunello winery, adding to the authentic experience.
Evening
End your Tuscan journey with a memorable dining experience at Pienza: Scenic hiking on the Gladiator's movie location. This unique tour combines scenic hiking with a gourmet meal served at one of the iconic filming locations from 'Gladiator.' Enjoy delicious food and wine while soaking in the cinematic landscape.
Bedtime
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Visit Pienza Guided E-bike Tour through the Val d'Orcia in Pienza
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Pienza: Guided E-bike Tour through the Val d'Orcia

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Visit Cooking Class in a Brunello Winery - Private experience in Pienza

Cooking Class in a Brunello Winery - Private experience

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