A Tuscan dream in four days, walled Monteriggioni stays, Chianti Classico tastings, villa cooking and San Gimignano towers, ending with Brunello in Montalcino and the serenity of Sant’Antimo.
A taste of Tuscany tour
4 Days/3 Nights
Starting from
$
per person*
Unforgettable Italian Journeys, Designed for You
Curated by passionate Italy experts, this sample itinerary is just the beginning of your Italian adventure. Every journey we design is unique, crafted around your interests, pace, and dreams so you can experience Italy’s beauty and culture like a true insider. Let us transform your vision into a one-of-a-kind travel experience, filled with authentic moments and lasting memories
Day 1
MONTERIGGIONI, SIENA
Walled Village Welcome, Siena by Candlelight
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Arrive and check in at your hotel in Monteriggioni
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Enjoy a welcome drink and time to relax
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Savor a welcome dinner at a traditional restaurant in Siena or Monteriggioni
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Overnight stay in Monteriggioni
Day 2
CHIANTI
Classico Sips, Siena’s Medieval Heart
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Breakfast at your hotel
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Excursion through the scenic Chianti region
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Guided tour and wine tasting at a renowned Chianti Classico winery
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Return to hotel and overnight stay
Day 3
SAN GIMIGNANO
Villa Cooking
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Morning hands-on Tuscan cooking class in a local villa, followed by lunch paired with local wines
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Dinner at your own pace
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Return to hotel and overnight stay
Day 4
VAL D’ORCIA, MONTALCINO
Brunello Cellars & Sant’Antimo Silence
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Breakfast at your hotel and check-out
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Scenic drive through Val d’Orcia to Montalcino
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Guided visit and wine tasting in a historic Brunello cellar
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End of services
MAKE THIS ITINERARY YOURS
Turn this sample itinerary into your dream Italy vacation – tailored to your pace, passions, and budget.
Day 1
MONTERIGGIONI, SIENA
Walled Village Welcome, Siena by Candlelight
Begin your Tuscan adventure with a warm welcome in Monteriggioni, a picturesque village surrounded by medieval walls and nestled in the heart of the Tuscan countryside, just a short drive from Siena. After checking in to your charming hotel, unwind with a refreshing welcome drink and take time to relax in this tranquil setting. In the evening, experience authentic Tuscan flavors with a welcome dinner at a traditional restaurant in either Siena or the Monteriggioni area. Enjoy your first overnight stay immersed in the beauty and heritage of Tuscany.
Day 2
CHIANTI
Classico Sips, Siena’s Medieval Heart
Start your day with a delightful breakfast at the hotel before venturing into the world-renowned Chianti region, famous for its rolling vineyards and exceptional wines. Enjoy a guided tour and exclusive wine tasting at one of the most celebrated Chianti Classico wineries, where you’ll learn about local winemaking traditions. In the afternoon, explore the historic center of Siena, renowned for its medieval architecture, vibrant piazzas, and the iconic Palio horse race. Return to your hotel for a restful overnight stay, with dinner at your leisure.
Day 3
SAN GIMIGNANO
Villa Cooking
Immerse yourself in the culinary traditions of Tuscany with a hands-on cooking class in a beautiful local villa, where you’ll prepare a full Tuscan menu and savor your creations paired with regional wines for lunch. Afterward, discover the enchanting town of San Gimignano, a UNESCO World Heritage Site famous for its medieval towers and well-preserved architecture. Enjoy free time to explore its charming streets before returning to your hotel for another comfortable overnight stay.
Day 4
VAL D’ORCIA, MONTALCINO
Brunello Cellars & Sant’Antimo Silence
After breakfast and check-out, journey through the breathtaking landscapes of Val d’Orcia to reach Montalcino, home to the world-famous Brunello di Montalcino wine. Enjoy a guided visit and exclusive tasting in a historic Brunello cellar, experiencing the depth and character of this renowned red wine. Complete your day with a suggested visit to the picturesque town center of Montalcino and the nearby Sant’Antimo Abbey, a stunning example of Romanesque architecture. Your unforgettable Tuscan tour concludes here, leaving you with lasting memories of Italy’s wine country.
