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5 Days Exploring Tuscany's Vineyards and Historic Cities

5 Days Exploring Tuscany's Vineyards and Historic Cities Itinerary

Last updated: 2024 Jul 01

Discovering Montalcino's Rich Heritage

Morning
Start your day with a visit to Montalcino. This charming town is renowned for its Brunello wine and offers stunning views of the surrounding countryside. Stroll through its medieval streets and soak in the history and culture.
Afternoon
In the afternoon, head to Montalcino Fortress (Fortezza di Montalcino). This imposing fortress offers panoramic views of the Tuscan landscape. Explore its ancient walls and learn about its historical significance.
Evening
End your day with a delightful wine tasting experience at Montalcino: Brunello Wine Tasting Experience. Enjoy a selection of fine wines paired with local delicacies, making for a perfect evening in Tuscany.
Bedtime
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Val d'Orcia Adventures and Culinary Delights

Morning
Begin your second day with an exciting tour: Val d'Orcia: Private Photography Safari Tour with Aperitif. Capture the breathtaking landscapes of Val d'Orcia while enjoying an aperitif amidst nature.
Afternoon
After your photography tour, indulge in a unique culinary experience with Val D'Orcia: Private Olive Oil Tasting and Tuscan Dinner. Learn about the production of olive oil and savor a delicious Tuscan dinner.
Evening
Conclude your day with a serene evening walk through the picturesque fields of Val d'Orcia. The golden hues of sunset will provide a perfect backdrop for relaxation.
Bedtime
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Historical Treasures and Scenic Views in Pienza

Morning
On your third day, visit the historic town of Pienza. Start with Pienza: Palazzo Piccolomini & Palazzo Borgia Entrance Ticket. These palaces offer insight into Renaissance architecture and history.
Afternoon
In the afternoon, embark on Pienza: Scenic hiking on the Gladiator's movie location. Enjoy stunning views as you hike through this iconic location featured in the film Gladiator.
Evening
Wrap up your day with a delightful dining experience at Pienza: Dining Experience at a Local's Home. Savor authentic Tuscan cuisine prepared by locals, providing an intimate glimpse into regional culinary traditions.
Bedtime
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Truffle Hunting and Wine Tasting in Trequanda

Morning
Start your day with an exciting adventure: Trequanda: Tuscan Truffle Hunting Experience with Lunch. Join expert truffle hunters and their dogs as you search for these prized delicacies in the woods. After the hunt, enjoy a delicious lunch featuring freshly found truffles.
Afternoon
After your truffle hunting experience, head to a nearby vineyard for Wine Tasting in Toscana with Priority Access. Savor a selection of fine Tuscan wines while learning about the winemaking process from local experts.
Evening
Conclude your day with a relaxing evening at La Chiusa. This highly-rated restaurant offers a cozy atmosphere and serves exquisite Tuscan cuisine, making it the perfect spot to unwind after a day of exploration.
Bedtime
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Exploring Montepulciano's Rich Flavors

Morning
Begin your final day with a visit to Montepulciano: Winery and Perfume Laboratory Sensory Tour. This unique tour combines wine tasting with a sensory experience in a perfume laboratory, offering an unforgettable start to your day.
Afternoon
In the afternoon, take part in Cooking Class in a Brunello Winery - Private experience. Learn how to prepare traditional Tuscan dishes under the guidance of expert chefs. Afterward, enjoy the fruits of your labor paired with Brunello wine.
Evening
End your trip on a high note with Val d'Orcia: Magical 3-Course Dinner under the Oak Tree. Dine under the stars amidst the enchanting landscape of Val d'Orcia, savoring a gourmet meal that perfectly encapsulates the essence of Tuscany.
Bedtime
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