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Romantic Tuscany Getaway: Wine, History, and Charm Itinerary

Last updated: 2024 Jun 14

Wine and Romance in Montalcino

Morning

Start your romantic getaway with a delightful breakfast at the charming La Grotta di Montepulciano, known for its traditional Tuscan cuisine. After breakfast, take a leisurely stroll through the picturesque streets of Montalcino, soaking in the romantic atmosphere of this medieval town.

Afternoon

For lunch, savor the local flavors at La Torre, a restaurant with panoramic views of the Tuscan countryside. In the afternoon, visit the iconic Montalcino Fortress (Fortezza di Montalcino) and enjoy a wine tasting at one of the renowned wineries in the area.

Evening

Conclude your day with a romantic dinner at Il Canto del Maggio, a Michelin-starred restaurant known for its innovative cuisine. Enjoy a candlelit dinner with your loved one, surrounded by the beauty of the Tuscan hills.

Bedtime

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4.78
Montalcino Fortress (Fortezza di Montalcino)
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Medieval Magic in San Gimignano

Morning

Indulge in a delicious breakfast at La Taverna di San Giuseppe, a historic restaurant in the heart of San Gimignano. After breakfast, explore the enchanting medieval streets of the town and visit the Santa Margherita Basilica (Basilica di Santa Margherita).

Afternoon

For lunch, enjoy the authentic Tuscan cuisine at Antica Trattoria Botteganova, a family-run restaurant with a cozy atmosphere. Spend the afternoon visiting the Castle of Meleto (Castello di Meleto) and the Temple of San Biagio (Tempio di San Biagio), soaking in the history and charm of the region.

Evening

In the evening, have a romantic dinner at La Bottega del Nobile, a restaurant known for its extensive wine list featuring the best of the region. Enjoy a candlelit dinner and savor the flavors of Tuscany.

Bedtime

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4.81
Santa Margherita Basilica (Basilica di Santa Margherita)
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5.00
Castle of Meleto (Castello di Meleto)
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Historic Elegance in Siena

Morning

Begin your day with a leisurely breakfast at Osteria Le Logge, a historic restaurant in the heart of Siena. After breakfast, explore the Siena Cathedral (Duomo di Siena) and the Piazza del Campo, immersing yourself in the rich history of the city.

Afternoon

For lunch, taste the traditional Sienese dishes at Enoteca I Terzi, a restaurant known for its local ingredients and authentic flavors. In the afternoon, visit the Siena Pinacoteca Nazionale and take a romantic walk through the Siena Historic Centre, a UNESCO World Heritage Site.

Evening

Enjoy a romantic dinner at Cibrèo Ristorante Firenze, a Tuscan institution known for its innovative approach to traditional cuisine. Savor the unique flavors and intimate ambiance of this renowned restaurant.

Bedtime

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4.61
Siena Cathedral (Duomo di Siena)
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4.50
Siena Historic Centre
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Renaissance Romance in Pienza

Morning

Start your day with a delicious breakfast at Osteria dell'Orsa, a cozy restaurant in the heart of Pienza. After breakfast, explore the Pienza Historic Centre and visit the Palazzo Piccolomini, a stunning Renaissance palace.

Afternoon

For lunch, enjoy the local pecorino cheese at La Porta, a restaurant with a panoramic terrace overlooking the Val d'Orcia. In the afternoon, take a romantic stroll through the Val d'Orcia, a picturesque valley dotted with vineyards and cypress trees.

Evening

Have a romantic dinner at Il Falconiere, a Michelin-starred restaurant located in a historic villa near Pienza. Indulge in a gourmet meal paired with the finest wines of the region, surrounded by the beauty of the Tuscan countryside.

Bedtime

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4.67
Pienza Historic Centre
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4.73
Palazzo Piccolomini
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Wine and Wellness in Montepulciano

Morning

Begin your day with a relaxing breakfast at Trattoria Da Burde, a charming restaurant in Montepulciano. After breakfast, visit the Temple of San Biagio (Tempio di San Biagio) and take a romantic walk through the vineyards surrounding the town.

Afternoon

For lunch, enjoy the local specialties at Osteria Acquacheta, a rustic restaurant known for its wild boar dishes. In the afternoon, relax and rejuvenate at the Terme di Montepulciano, a thermal spa with panoramic views of the Tuscan countryside.

Evening

Conclude your day with a romantic dinner at La Bottega del Nobile, a restaurant known for its extensive wine list featuring the best of the region. Enjoy a candlelit dinner and savor the flavors of Tuscany.

Bedtime

Find amazing hotels in Montepulciano, Tuscany, Italy.

4.55
Temple of San Biagio (Tempio di San Biagio)
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Cultural Escape in Cortona

Morning

Enjoy a leisurely breakfast at Trattoria Mario, a historic restaurant in the heart of Cortona. After breakfast, explore the Diocesan Museum of Cortona and take a romantic walk through the Cortona Historic Centre, with its medieval charm and panoramic views.

Afternoon

For lunch, taste the traditional Tuscan cuisine at Osteria Le Logge, a renowned restaurant with a focus on local ingredients. In the afternoon, visit the Fortress of Girifalco and the Santa Maria Nuova (Chiesa di Santa Maria Nuova), immersing yourself in the history and culture of the region.

Evening

Conclude your romantic getaway with a farewell dinner at La Taverna di San Giuseppe, a family-run restaurant known for its warm hospitality and authentic Tuscan dishes. Raise a glass of local wine to a memorable trip in the heart of Tuscany.

Bedtime

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