Explore Tuscany’s medieval towns, iconic castles, and celebrated wine estates. Enjoy tastings, cooking classes, and authentic local flavors on a guided journey through Italy’s heartland.
Starting from $.
Independent Tuscany wine tour
7 Days/6 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
Medieval Architecture, Modern Appetite
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Arrive in Monteriggioni and check in to your hotel.
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Short drive to Siena for a half-day guided sightseeing tour.
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Enjoy leisure time for shopping and lunch in Siena.
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Visit the renowned Enoteca Italiana inside the Medici Fortress for a wine seminar and tasting with a professional sommelier.
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Return to Monteriggioni for an overnight stay
Day 2
THE VERNACCIA DI SAN GIMIGNANO
Where White Wine Finally Gets Center Stage
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Breakfast at your hotel, then depart for San Gimignano
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Explore San Gimignano at your own pace.
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Visit a local wine estate for a guided tasting of Vernaccia di San Gimignano D.O.C.G.
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Optional afternoon visit to Volterra
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Return to the hotel for dinner on your own and overnight stay.
Day 3
THE CHIANTI CLASSICO
A Tasting Day With A Savory Finish
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Breakfast, then scenic drive along the Chianti Castle Road.
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Optional visit to Brolio Castle and guided tour of a Chianti Classico-producing castle, including wine tasting.
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Afternoon visit to the medieval hamlet of Radda in Chianti.
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Return to Monteriggioni for dinner on your own and overnight stay.
Day 4
THE BRUNELLO DI MONTALCINO
Where The Aromas Turn Savory And Complex
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Visit two prestigious Brunello wine cellars with guided tastings by expert winemakers.
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Free time for lunch and to stroll through the medieval village of Montalcino
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Visit the historic Abbey of Sant’Antimo
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Return to the hotel for dinner on your own and overnight stay
Day 5
TUSCAN COOKING CLASS
From Recipe Cards To Real Memories
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Breakfast, then hands-on Tuscan cooking class in a local villa
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Enjoy lunch featuring your culinary creations
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Afternoon at leisure for relaxation or shopping
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Return to Monteriggioni for dinner on your own and overnight stay
Day 6
THE VINO NOBILE DI MONTEPULCIANO
Where The Red Feels Polished From Start To Finish
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Morning visit to one of Italy’s oldest wine cellars in Montepulciano
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Guided walking tour of Montepulciano’s historic center.
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Tasting-lunch at a local wine estate
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Afternoon visit to the picturesque town of Pienza
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Return to Monteriggioni for dinner on your own and overnight stay
Day 7
MONTERIGGIONI
Last Day For A Final Toast Inside The Walls
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Breakfast at the hotel and check out
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End of our 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
Medieval Architecture, Modern Appetite
Arrive in the enchanting medieval village of Monteriggioni and check in to your hotel, perfectly situated for exploring the heart of Tuscany. Embark on a scenic drive to the historic city of Siena, renowned for its stunning medieval architecture and vibrant piazzas. Enjoy a half-day guided sightseeing tour of Siena, uncovering its rich history, iconic landmarks, and charming local shops. Take time at leisure to indulge in authentic Tuscan cuisine and boutique shopping.
In the afternoon, experience a unique visit to the prestigious Enoteca Italiana, one of Italy’s most celebrated wine cellars, nestled within the Renaissance ramparts of the Medici Fortress. Discover a remarkable collection of over 600 D.O.C. and D.O.C.G. Italian wines, representing more than 2,000 brands from every wine-producing region in Italy. Participate in an exclusive wine seminar led by a professional sommelier, featuring tastings of four distinguished Tuscan wines.
Conclude your first day in Tuscany with a memorable welcome dinner in a medieval restaurant in Siena, savoring local flavors in an atmospheric setting. Return to Monteriggioni for a restful overnight stay, ready to continue your Tuscan adventure.
Day 2
THE VERNACCIA DI SAN GIMIGNANO
Where White Wine Finally Gets Center Stage
Start your day with a delicious breakfast at the hotel before departing for the captivating medieval town of San Gimignano, renowned for its iconic stone towers and picturesque hilltop views. Enjoy time to explore San Gimignano at your own pace, discovering its charming streets, artisan shops, and historic landmarks.
Later, immerse yourself in Tuscany’s wine culture with a visit to a renowned local estate specializing in the celebrated Vernaccia di San Gimignano D.O.C.G. white wine. Experience a guided wine tasting session led by the estate owners, paired with authentic local delicacies for a true taste of the region. Savor a light tasting lunch surrounded by the scenic beauty of the Tuscan countryside.
In the afternoon, consider a visit to the nearby ancient town of Volterra, famous for its Etruscan heritage and artisan craftsmanship. Return to your hotel in Monteriggioni in the late afternoon. Enjoy dinner at your leisure and unwind with an overnight stay, ready for another day of Tuscan discovery.
Day 3
THE CHIANTI CLASSICO
A Tasting Day With A Savory Finish
Begin your day with a hearty breakfast before setting out on a scenic drive through the world-famous Chianti region, one of the most beautiful and iconic areas in Tuscany. Travel along the renowned “Road of Chianti Castles,” with the option to visit the historic Brolio Castle, a symbol of Tuscan heritage and winemaking tradition.
Experience an exclusive stop at a charming castle estate, celebrated for producing the prestigious D.O.C.G. Chianti Classico red wine. Enjoy a guided tour of the castle’s impressive interiors and ancient wine cellars, followed by a curated wine tasting led by the estate owner.
After lunch at your leisure, spend a relaxing afternoon exploring the picturesque medieval hamlet of Radda in Chianti, often regarded as the heart of the Chianti Classico region. Wander the cobblestone streets, soak in the authentic Tuscan atmosphere, and discover local boutiques and cafes.
Return to Monteriggioni in the late afternoon. Enjoy dinner on your own and a restful overnight stay at your hotel, surrounded by the timeless beauty of Tuscany.
Day 4
THE BRUNELLO DI MONTALCINO
Where The Aromas Turn Savory And Complex
Embark on an unforgettable journey into the world of Brunello di Montalcino, one of Tuscany’s most celebrated red wines. Today’s tour includes exclusive visits to two of the region’s most prestigious wine cellars, where expert winemakers will guide you through the fascinating process of crafting Brunello wine. Enjoy guided tastings and gain insider knowledge about the unique terroir and winemaking traditions that make Brunello di Montalcino world-renowned.
Take time for lunch at your leisure, then explore the enchanting medieval village of Montalcino, famous for its picturesque streets and vibrant local culture. Continue your discovery with a visit to the historic Abbey of Sant’Antimo, a remarkable Romanesque monastery founded, according to legend, by Charlemagne in 781.
Return to your hotel in Monteriggioni in the evening. Enjoy dinner on your own and relax with an overnight stay, reflecting on your immersive Tuscan wine experience.
Day 5
TUSCAN COOKING CLASS
From Recipe Cards To Real Memories
Start your day with a light breakfast at the hotel before heading to a picturesque Tuscan villa for an immersive cooking class. Enjoy a hands-on culinary experience as you learn traditional Italian recipes from a local chef, using fresh, regional ingredients. Participate in every step of the cooking process, gaining valuable insights into authentic Tuscan cuisine.
After the class, savor a delicious lunch featuring the dishes you’ve prepared, surrounded by the charm of the Tuscan countryside. Spend the rest of the afternoon at your leisure, relaxing, exploring local shops, or simply soaking in the serene atmosphere.
Return to Monteriggioni in the evening. Enjoy dinner on your own and unwind with a comfortable overnight stay, enriched by your new culinary skills and unforgettable memories.
Day 6
THE VINO NOBILE DI MONTEPULCIANO
Where The Red Feels Polished From Start To Finish
Discover the Renaissance charm of Montepulciano, often hailed as the “pearl of the Renaissance” and renowned for its world-class Vino Nobile di Montepulciano red wine. Begin your day with a visit to one of Italy’s oldest wine cellars, located in the heart of Montepulciano. Marvel at the Renaissance arches and explore The Etruscan burial chambers carved from the ancient tufa rock beneath the cellar.
Continue your journey with a guided walking tour of Montepulciano’s town center, taking in its elegant palaces, historic squares, and local culture. Next, transfer to a prestigious wine estate, where you’ll enjoy a memorable tasting-lunch in the atmospheric cellars, sampling exceptional Vino Nobile alongside regional specialties.
In the afternoon, take time at leisure to explore the nearby town of Pienza, celebrated for its countryside views and charming Renaissance architecture. Return to Monteriggioni in the evening. Dinner on your own and overnight stay, savoring the flavors and beauty of Tuscany.
Day 7
MONTERIGGIONI
Last Day For A Final Toast Inside The Walls
After breakfast, check out from the hotel, marking the end of our services and your unforgettable journey through Umbria. Safe travels and arrivederci!
