Our Email:  info (at) old world tours.eu

Castles & Wine: Italy

A Journey to Remember: Discovering Italy's Most Celebrated Wine Regions.

Key Features

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Trip duration: 

14 Days / 13 Nights

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Countries visited:

Italy

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Activity level:

Moderate to Active

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Transportation:

Executive Class Coach

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Accommodation:

Hand-picked Superior Hotels

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Max group size:

18 Travellers

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Trip price (pp):
Single Supp:

EUR 5.900,-
EUR 1.200,-

“Wine is the poetry of the earth” – Mario Soldati, 1907-99, Writer and Director

Italy, the world’s largest and one of the oldest wine producers, offers a viniculture that is deeply woven into its landscapes and history. Our Castles & Wine: Italy Tour invites you to immerse yourself in this rich heritage, experiencing not only remarkable wines but also breathtaking scenery and exceptional cuisine. This two-week journey focuses on the celebrated regions of Piedmont, Tuscany, and Veneto, each renowned for its distinct wines, storied history, and vibrant culture. Along the way, you will tour magnificent castles, stroll through historic estates, and connect with passionate winemakers eager to share their craft. It’s an unforgettable exploration of Italy’s finest wine traditions and timeless charm.

Our journey begins in the heart of Piedmont, a region celebrated for its rich, complex reds and breathtaking scenery. We’ll dive into the world of legendary Barolo and Barbaresco wines, touring acclaimed wineries and savoring tastings of these exceptional vintages. A special highlight is the Truffle Festival in Alba, offering an authentic taste of a fascinating local tradition. From Piedmont, we travel to the coastal beauty of Liguria, where we’ll spend a full day exploring the stunning Cinque Terre. Here, we’ll sample unique local wines perfectly paired with fresh seafood as we take in the vibrant seaside atmosphere. The first week concludes in enchanting Tuscany, renowned for its robust wines and iconic landscapes. We’ll enjoy Vernaccia di San Gimignano amid the town’s awe-inspiring medieval setting. We indulge in the depth of Vino Nobile di Montepulciano while taking in the sweeping, pastoral vistas of the Val d’Orcia. Each destination promises unforgettable experiences that capture the essence of Italy’s winemaking heritage.

We begin the second week still amid the iconic rolling hills of Tuscany, visiting Montalcino to savor the elegance of Brunello wines. Next, we spend a full day in the famed Chianti region, where we’ll enjoy tastings of its classic Sangiovese wines and soak in the region’s rustic charm. From Tuscany, we venture to Emilia-Romagna, a region celebrated for its outstanding cuisine. Here, we’ll explore Rocchetta Mattei, a spectacular fairy-tale castle, and enjoy a true foodie experience in Parma, complete with a behind-the-scenes tour of a Parmigiano Reggiano producer. In Veneto, we enter the ancient, walled city of Verona and immerse ourselves in the world of Amarone di Valpolicella and Bardolino. Touring historic vineyards, we’ll sample these bold, full-bodied wines and uncover the stories behind their craftsmanship. Finally, in Lombardy, we’ll indulge in the refined flavors of Franciacorta, Italy’s answer to Champagne, and explore the rarity of Moscato di Scanzo. Each region offers its own unique, unforgettable contributions to Italy’s rich tapestry of wine and culture.

Typical wine imagery in Tuscany

Our accommodations are carefully chosen 4-star hotels in charming towns, providing both comfort and an authentic connection to local life. Many meals are included, featuring traditional Italian dishes, regional specialties, and thoughtfully curated wine pairings that showcase each area’s unique flavors. Whether you’re an experienced oenophile or new to Italian wines, our Castles & Wine Italy Tour promises a richly immersive journey through Italy’s most celebrated wine landscapes. Each week brings its own unique discoveries, with the flexibility to join for either week* or enjoy the full two-week experience for a comprehensive dive into Italy’s finest wine regions.

* Please see details of the options in the tabs below.

Our Castles & Wine: Italy tour is an unforgettable two-week journey through Italy’s most renowned wine regions, designed for wine lovers and cultural explorers alike. This immersive trip offers a unique blend of Italy’s finest wines, rich history, and charming local culture, while staying in small, picturesque towns that provide an authentic Italian experience away from the main tourist paths.

Itinerary Overview

Day 1:  Monferrato and the Langhe: The Heart of Piedmont’s Wine Country
Day 2: 
The Essence of Barbaresco and the Magic of Truffles
Day 3: 
Breathtaking Barolo
Day 4: 
Wine Cooperatives and the Scenic Ligurian Coast
Day 5:  The
Magnificent Cinque Terra
Day 6:  Carrara Marble and the Timeless Charm of San Gimignano
Day 7:  Montepulciano and the Grandeur of Val d’Orcia

Day 8:  Flex Day: Orvieto

Day 9:  Chianti: The Soul of Tuscany
Day 10:  Discovering Scansano and Montalcino
Day 11:  A Fairy Tale Palace and Italy’s Culinary Heartland
Day 12:  The Flavors of Parmesan and the Charm of Verona
Day 13:  Lake Garda and the Valpolicella Wine Country
Day 14:  Journey Through Lombardy to the Shores of Lake Como
Day 15:  Arrivederci

For guests only doing Week 1, Day 8 is: Tuscany to Orvieto to Rome (flight possible the following day)
For guests only doing Week 2, Arrival Day is Day 8: Rome to Orvieto to Tuscany

For Hotel and amenities Overview, please see the Includes tab.

Day 1: Monferrato and the Langhe: The Heart of Piedmont’s Wine Country

Another beautiful vineyard in the Langhe, Piedmont, Italy

Our tour begins in the late morning at Milan Malpensa Airport. From there, we journey through the broad Lomellina rice fields, where much of Italy’s risotto rice is cultivated. Entering the Piedmont region, we make our first stop in Monferrato, a renowned wine district celebrated for its diverse selection of wines and unique Infernot — hand-carved, underground cellars that offer ideal wine storage conditions. Here, we’ll explore one of these remarkable cellars and visit the local wine shop to sample regional varieties.

Next, we continue to the Langhe region, home to the renowned Barolo wines. If Barolo is the heart of the Langhe region, the Nebbiolo grape is its soul. We'll arrive at our hotel near Barolo by mid-afternoon, allowing you ample time to settle in and unwind before our special Welcome Dinner with breathtaking views over the rolling vineyards.

Included:

Included:


Barrels In A Wine Cellar

Our journey continues into the breathtakingly beautiful Barbaresco region, where densely planted vineyards line the steep hillsides like meticulously tended gardens. At our first stop, we dive into the magic of Barbaresco with a tasting at one of the region’s most acclaimed wineries, including a glimpse into its remarkable cellar. Our next visit takes us deeper into another historic cellar, where you'll learn about 'crunchy bubbles' and the classic method of crafting sparkling wine.

After lunch, we’ll enjoy a relaxed visit to the charming town of Barbaresco and its regional wine shop. Here stands the tallest tower in the region, a lasting remnant of a former castle. From Barbaresco, we continue to Alba, the region’s bustling trade center and host of the world’s oldest White Truffle Fair, taking place during our visit. You’ll have the opportunity to delve into the fascinating world of truffles, from traditional truffle hunts to the art of preparing this prized delicacy. Enjoy dinner on your own in Alba before we return to the hotel.

Included:


Sunrise on the hills of Barolo, Piedmont, Italy

Today, Barolo takes center stage as we explore the region, moving from village to village and taking in the charm of the towns and the grandeur of the landscapes. Our first castle visit of the trip is to Grinzane Cavour, where we’ll enjoy an inside tour and browse its own wine shop—a perfect stop in the heart of Barolo country. We’ll also have immersive visits with two esteemed winemakers, one in La Morra to the north and another in Monforte d'Alba to the south. These visits will serve as a Master Class in cultivating Nebbiolo grapes and crafting exceptional Barolo wines.

Today’s lunch offers a special treat—a panoramic view of vineyards draping the rolling hills. We return to Barolo in time for you to explore the charming and quirky Corkscrew Museum. Dinner will be on your own this evening.

Included:


Church of St. Peter at Porto Venere in Liguria, Italy

Heading south, we visit the heart of the wine cooperatives in southeastern Piedmont, where small, family-run vineyards thrive. Our first stop is the regional wine house in Nizza Monferrato, where you’ll have the chance to taste some of the finest Barbera wines. We then continue to the charming town of Gavi, celebrated for its renowned Gavi di Gavi, a distinguished white wine made from the Cortese grape. After lunch in Gavi, we’ll visit the local cooperative’s wine house before departing Piedmont.

Our scenic drive through Liguria takes us along the stunning Mediterranean coastline, renowned for its pesto, fresh seafood, and exceptional olive oil. We arrive in La Spezia, our home for the next two nights, just in time for a special treat: a visit to an olive oil producer. Tonight, we’ll gather for a group dinner in La Spezia.

Included:


Colorful Manarola in Cinqueterre Italy

Cinque Terre, a UNESCO World Heritage site since 1997 and a must-see for many travelers, consists of five vibrant fishing villages nestled along the Ligurian coast. Each town boasts its own unique charm and beauty. Rather than rushing to visit all five villages in one day, we choose a more relaxed and photogenic approach by exploring the two most stunning towns by boat. This allows for more quality time in each village and offers breathtaking views from the sea.

We begin our day with a visit to the charming town of Porto Venere, a favorite haunt of renowned writers and poets. From there, we’ll take a boat to Vernazza, officially recognized as one of the most picturesque towns in Italy. You’ll have approximately three and a half hours to explore the town and enjoy lunch, with many of the best photo opportunities located in the surrounding hills. Afterward, we’ll board a boat to Manarola, where you’ll have two hours to uncover the secrets of this fascinating fishing village. We’ll catch the last boat back to La Spezia, where you can enjoy dinner at your leisure.

Included:


Medieval Town of San Gimignano

Castles are built from stone, but palaces are crafted with a more luxurious material: marble. Today’s first special treat is a visit to the renowned Carrara marble quarries, perched high above the Mediterranean at the edge of Tuscany. Michelangelo famously carved Carrara marble, and this exquisite stone was used in the construction of landmarks such as the cathedral in Pisa and the U.S. Capitol Building. We’ll explore the history of this versatile stone and gain an up-close view of how it is cut and transported, taking 4x4 vehicles with local guides deep into the mountains.

Our second highlight today is the enchanting walled hill town of San Gimignano, famed for its well-preserved medieval architecture and iconic skyline. Surrounded by seemingly endless olive groves and vineyards, San Gimignano is also the birthplace of the celebrated Vernaccia white wine. We arrive in time for lunch and have a few hours to explore this beautifully preserved medieval town. Afterward, we continue to our hotel in central Tuscany, where we’ll settle in for the next five nights. This evening, enjoy a group dinner at a local restaurant featuring authentic Tuscan cuisine.

Included:


Rolling hills in Tuscany, Italy

Day 7 is dedicated to exploring the breathtaking hills and valleys of the Val d'Orcia region, Tuscany's most photographed landscape. The drive itself is peaceful and picturesque. Our first stop is the charming town of Pienza, a UNESCO World Heritage site celebrated for its Renaissance architecture and known as the unofficial capital of pecorino cheese. From Pienza, we’ll continue on to the enchanting town of Montepulciano, stopping along the way to capture photos of Tuscany’s iconic cypress trees.

Montepulciano, an impressive hilltop town with a blend of medieval and Renaissance charm, is a gem of unique beauty. Set high above a postcard-perfect landscape of vineyards, grain fields, olive groves, and cypress trees, it is the quintessential Tuscan town. This area is also among the world’s finest wine-making regions and the birthplace of the prestigious Vino Nobile - our first encounter with the esteemed Sangiovese grape. We’ll have the entire afternoon to explore Montepulciano, including a visit to one of the city’s premier wineries. Upon returning to our hotel, you’ll have the evening free to enjoy dinner on your own.

 

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Old Italian Street With Vespa

The flexible design of our Castles & Wine Italy tour tailors the Day 8 itinerary to the version you’ve chosen — whether it’s the full tour, the first week only, or the second week only. All three versions include a visit to the charming hilltop town of Orvieto in Umbria. A true Italian gem, Orvieto offers a blend of history, art, culture, natural beauty, and its own renowned white wine, Orvieto Classico. Each tour variation allows ample time to stroll the picturesque streets and enjoy lunch. We’ll also make a special stop at a nearby winery, where you’ll enjoy excellent wines and pleasant views of the town.

The full tour version does offer some other options. Please see the Extensions tab for details on the itineraries of each version of the tour.

Included:


Barone Ricsoli worked on the Chianti appellation at Castle Brolio

Chianti Classico is perhaps Italy's most iconic wine and certainly the best-selling red from Tuscany. We dedicate an entire day to exploring the Chianti region, where we’ll experience the exquisite vintages crafted from the revered Sangiovese grape. Though Chianti may not boast the dramatic landscapes of Barolo or Val d'Orcia, it holds its own charm, with a picturesque mix of dense forests, rolling vineyards, patterned olive groves, and quaint, rustic villages.

Our journey begins in the north, working our way south through the heart of Chianti. We start with a tasting at a picture-perfect castle winery, then pause for a coffee break in the charming town square of Greve in Chianti. From there, we make our way to the enchanting hilltop town of Radda in Chianti, surrounded by vineyards, where we’ll enjoy a memorable wine-pairing lunch. Afterward, there's time to explore the town's boutiques or visit a cozy winery bistro. In the afternoon, we’ll visit the historic Castello Brolio, birthplace of the Chianti appellation. Upon returning to our hotel, the evening is yours to relax and dine at your leisure.

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Dreamy Landscape in Val d'Orcia, Tuscany

Our final full day in Tuscany! Have we saved the finest expression of the Sangiovese grape for last? That’s for you to decide, but Brunello di Montalcino is undoubtedly one of the world’s most acclaimed wines. Today, we embark on an in-depth journey into the heart of Brunello in the charming medieval town of Montalcino.

But first we begin with a drive a bit further south to the Maremma region near Grosseto, where the Etruscans once cultivated wine. Here, we visit the quaint hillside town of Scansano, birthplace of Tuscany's best kept secret, Morellino di Scansano. At the regional wine house, we’ll uncover the nuances of this unique, sea-breeze-infused vintage made from the beloved Sangiovese grape.

Then it’s back to Val d'Orcia and Montalcino, where we have over four hours to immerse ourselves into the town and the world of Brunello, Italy’s longest oak-cask-aged wine. After a leisurely lunch, we delve deeper into this renowned appellation at the Brunello Winegrowers Consortium, where we’ll gain insight into the terroir, craftsmanship, and dedication behind this exceptional wine. You’ll also have time to wander the town and taste the fruits of its rich wine tradition. We’ll return to our hotel in the evening, where you’re free to relax and enjoy dinner at your leisure.

Included:


Aerial view of Rocchetta Mattei Castle

Our journey brings us to Emilia-Romagna, the birthplace of many of Italy's most iconic foods and renowned pasta specialties that have captivated the world. Our first stop is the enchanting Rocchetta Mattei, a beautifully restored 19th-century fairy-tale castle. Built by an eccentric nobleman who gained fame as a self-taught healer, this unique structure is an eclectic blend of architectural styles, forming a mesmerizing maze of hallways, staircases, and hidden passages.

We then pause for lunch in the picturesque hills west of Bologna, where a unique microclimate nurtures thriving vineyards. This area is home to Colli Bolognesi Pignoletto, one of only two DOCG wines in Emilia-Romagna. By mid-afternoon, we reach Parma, where we’ll enjoy a food and wine tour through the heart of the city, followed by time to unwind at our hotel before an indulgent wine-pairing dinner. In Emilia-Romagna, every meal is a celebration of quality ingredients, artisanal traditions, and masterfully balanced flavors, making it a true paradise for food lovers.

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Delicious, crumbly, genuine Parmesan Cheese

This morning, we’ll visit an official Parmigiano Reggiano producer for an exclusive, behind-the-scenes look at the creation, storage, and handling of this remarkable cheese. Experience the rich sensory journey of Parmigiano Reggiano production and discover how a thousand years of tradition, craftsmanship, and passion come together to produce a truly inimitable dairy masterpiece.

Our next stop is Mantua (Mantova), a treasure trove of Italian art and architecture, where we’ll explore the stunning Ducal Palace before enjoying lunch. This palace is Italy’s largest architectural museum complex and a UNESCO World Heritage Site. From here, we head to the captivating city of Verona, often called the “Gateway to Italy.” Known for its vibrant history, culture, music, and architecture, Verona invites us to explore its old town on a walking tour. We’ll visit notable sites, including the Roman amphitheater, Castelvecchio (the old castle), and, of course, Juliet's famous balcony. Tonight, we’ll enjoy a special dinner to conclude an unforgettable day.

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Rocca Scaligera at Lake Garda, Italy

We begin the day with a visit to the extraordinary Castello Scaligero, a striking 14th-century fortress set on a narrow peninsula along the southern shore of Lake Garda. This beautifully preserved castle, surrounded by water, showcases classic medieval architecture—imposing, powerful, and monumental. After exploring the castle's impressive interior, we’ll enjoy a scenic drive along the lake, arriving in Bardolino for a relaxing lakeside lunch, naturally paired with a fine Bardolino vintage.

Our afternoon is devoted to the distinguished Amarone, the crown jewel of Valpolicella wines. Crafted uniquely from dried grapes, Amarone is renowned for its remarkable aging potential and complex flavor profile. Amidst Valpolicella’s rolling hills, we’ll visit two esteemed producers of this richly fruity yet dry, velvety, full-bodied wine. Tonight, you’ll have time to explore Verona and enjoy dinner at your leisure.

Included:


View Of Nice Italian Sunny Summer Countryside Landscape

Today, we head west along the Strada del Franciacorta, a scenic wine trail winding through rolling hills dotted with patchwork vineyards, towers, castles, and charming stone villages, leading to the southern shores of Lake Iseo. Here, you’ll have the opportunity to taste Franciacorta’s celebrated sparkling wines, crafted in the traditional méthode champenoise. We then travel along picturesque back roads to Bergamo, a lively city with a medieval core. Taking a funicular to the historic upper town—protected by impressive Venetian walls — we’ll explore and enjoy lunch. You may want to sample some unique local dishes, such as capù (gratin-stuffed cabbage dumplings), polenta taragna, or casoncelli, a beloved stuffed pasta.

Our journey continues with a scenic stop at Lake Como, where we’ll pause for a cappuccino and photos before arriving at our country manor hotel north of Milan’s airport. You’ll have ample time to relax and prepare for tomorrow’s flight before we gather for a memorable farewell dinner on the beautiful shores of Lake Varese.

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Thank You Danke Merci Grazie

It’s time to say Arrivederci as we take you to Milan Malpensa Airport for your journey home.

Included:


Adult: 18 & over -
Single Supplement:

Approved   What’s Included in Your Tour:

  • Door-to-Door Transportation – Enjoy seamless transfers throughout the tour.
  • All-Inclusive Pricing – Entrance fees, local guide fees, and taxes are all covered.
  • No Hidden Costs – Rest easy knowing there are no surprise charges or surprise optional add-ons.
  • Priority Access – Skip the lines at top attractions for a stress-free experience.
  • Expert Tour Director – Travel with a friendly, knowledgeable guide who brings history to life.
  • Specialized Site Guides – Expert-led tours at key sites add depth and authenticity to your experience.
  • Rich Historical Insights – Discover fascinating stories and context for every destination.

Thumb Up Mod   Our Exclusive Touch:

  • Guaranteed Departures – No minimum group size; your tour will always run as planned.
  • Small Group Experience – Enjoy a more personal experience with a maximum of 18 participants.
  • Stress-Free TravelOur well-paced schedule balances key highlights with discoveries and is designed to minimize packing and maximize enjoyment.
  • Hidden Gems Included – Explore a unique mix of iconic attractions and off-the-beaten-path treasures.
  • Inclusive Dining Options – Included meals offer generous menu options for every dietary preference.
  • Drinks on Us – Each included meal features two complimentary beverages.

About Info   Know Before You Go:

  • English-Language Tour – All commentary and guidance are provided in English.
  • Active Exploration – Expect plenty of walking, including in vineyards, castles, and medieval towns. The surfaces will often be uneven (see photo below); comfortable, sturdy shoes are essential.
  • Accessibility Note – Some of the historical venues we visit are not fully accessible; this tour requires good physical health and no significant mobility challenges.
  • Prepare for Varied Weather – Layered clothing is key to staying comfortable.
  • Travel Light – Large suitcases can be cumbersome; pack compactly to keep pace with the tour.
  • More Travel Tips – Visit our Travel Tips page for additional advice.

Cobblestone Street in a Medieval Town in Germany
Streets can be like this

Route

Castles & Wine: Italy Map