Tailor-Made Wine
Tours in Italy

Experience a trip of a lifetime through Italy where the food and wine take center stage while the landscape and history provide a stunning backdrop.

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Luxury Multiday Wine Tours in Italy

Your private tour of Italy awaits

Immerse yourself in the allure of Italy, where centuries of craftsmanship have refined world-renowned wines, complemented by delectable cuisine crafted from locally sourced ingredients. A dream destination for wine enthusiasts and foodies, Italy offers an unforgettable and luxurious experience.

Discover the country's diverse wine regions, each offering a rich tapestry of flavors waiting to be explored. From savoring the iconic Chianti Classico in the heart of Tuscany, to indulging in the elegance of Barolo in Piedmont, Italy unveils itself as an unrivaled paradise for wine lovers.

With incredible landscapes like the Amalfi Coast, Lake Como and Cinque Terre, private walking tours or yacht charters are always a highlight. Soak in the history from local tour guides and drivers, private tours of estates, or popular places like the Vatican Museum. 

Beautiful Tuscany

Tuscany

One cannot mention Tuscany without highlighting its famous wines. From Brunello through Chianti, to the vines of Sassicaia and Ornellaia, the Super Tuscans, Tuscany’s more than 10,000 years of history is unrivaled.

Sangiovese is the most prominent grape variety in this region, producing renowned reds such as Chianti, Brunello di Montalcino, and Vino Nobile di Montepulciano. These wines are known for their bold flavors and high quality, making them a favorite around the world.

Explore Tuscany on a private, tailor-made trip adding as much or as little wine-related touring as you desire. Take a Chianti winery tour as a day trip en route to other regions or immerse yourself in everything Tuscany on a multi-day guided tour. Either way, we’re here to help ensure your private multiday trip to Tuscany pairs the best experiences with ample free time to relax and savor the bounty of this incredible region.

Highlights

Experience Brunello di Montalcino: Savor award-winning wines, revered the world over for their bold, rich flavors and exquisite craftsmanship. Visit small family-run vineyards and pause to enjoy lunch with wine pairings right at the property. Or explore some of the most Iconic Wineries in the region.

Charming medieval towns: The region boasts some of the most beautiful and well-preserved towns, each with its own unique charm and history. Have time to explore at your own pace.

Florence's art & architecture: Discover Florence's rich artistic heritage with options that include visiting the Uffizi Gallery, home to an impressive collection of Renaissance art, wandering through the Piazza del Duomo to admire the Cattedrale di Santa Maria del Fiore, or marveling at Michelangelo's famous sculpture, David. Explore these iconic sites at your own pace and immerse yourself in the beauty of Florence. 

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Piedmont

More than just a wine destination, Piedmont offers top-notch hiking in the Italian Alps, along with numerous nature and national parks that make guided walking tours a must-do. Our local private tour guides will lead you off the beaten path, unveiling charming villages and stunning landscapes while sharing the rich history and culture of this region.

In addition to its stunning natural scenery, Piedmont is also known for its delectable cuisine. Truffles, porcini mushrooms, and hazelnuts are just some of the local delicacies that can be found in traditional dishes such as risotto, agnolotti pasta, and braised meats. Adding in guided food-focused tours, you will have the chance to taste these delicious flavors while learning about their origins and cultural significance.

Highlights

Delectable treasure: Piedmont is home to the world's most prized truffles, including the highly sought-after white truffle.

Chocolate: Turin is the birthplace of Gianduja, a type of chocolate made with hazelnuts.

Rustic and wholesome food: Piedmontese cuisine is known for its hearty, meat-based dishes like bollito misto, brasato al Barolo, and agnolotti.

The foot of the mountains: Piedmont is home to the Italian Alps, including the highest peak in Italy, Monte Bianco.

The "other" Italian car: The city of Turin is the birthplace of the famous Italian car brand, Fiat. The city also has several museums dedicated to Italian car design and engineering.

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Veneto

Venturing into the heart of Veneto, unveils a landscape steeped in vinicultural heritage and enriched by a tapestry of grape varieties that are as diverse as they are distinctive. This revered wine region is a symphony of rolling hills, ancient vineyards, and sun-drenched valleys—a testament to the enduring bond between land and vine. Veneto's terroir is a unique amalgamation of climatic conditions and soil compositions that range from the volcanic soils of the eastern hills to the calcareous clay of the Valpolicella area. It's this extraordinary terroir that nurtures the growth of some of Italy's most celebrated wines.

What sets Veneto apart is not just its storied history or picturesque landscapes but its ability to produce a wide array of wines—from the bold and robust Amarone to the delicate and aromatic Prosecco. The secret lies in the region's diverse microclimates, each fostering different grape varieties to their utmost expression.

In essence, Veneto represents an exquisite blend of tradition and innovation, nature and nurture. It invites connoisseurs and novices alike to explore its bounty, promising an unforgettable journey through one of Italy's most cherished wine regions.

Highlights

Famous food fare: Venetian cuisine is known for its seafood dishes, such as baccalà, sarde in saor, and risotto di gò. The region is also famous for its traditional dessert, tiramisù.

Palladian architecture: Veneto is home to several stunning examples of Renaissance architecture designed by the famous architect Andrea Palladio, including the Villa Capra and the Teatro Olimpico.

Majestic Mountains: The Veneto region includes part of the Dolomite Mountains, a UNESCO World Heritage Site known for its stunning natural beauty and opportunities for outdoor activities such as skiing, hiking, and rock climbing.

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Puglia

Nestled in the sun-drenched heel of Italy's boot, Puglia is a region that has quietly risen to prominence in the world of wine. Best known for its robust and hearty red wines, this enchanting locale offers a unique blend of varietals that reflect its rich history and diverse terroir. 

Among its most celebrated offerings are the Primitivo, known internationally as Zinfandel, which delivers a bold and spicy flavor profile, and the Negroamaro, which charms with its complex layers of fruit and earthy undertones. The uniqueness of Puglia as a wine region lies not only in its distinctive grape varieties but also in its ancient viticulture traditions that have been passed down through generations. 

Here, the warm Mediterranean climate and fertile soils combine to create conditions that are ideal for producing wines with intense flavors and deep character. As visitors explore this vibrant wine region, they're invited to discover not just the exceptional quality of Puglian wines but also the passion and craftsmanship that go into every bottle. 

Highlights

Unique trulli houses: The town of Alberobello is particularly famous for its collection of trulli houses, which are a UNESCO World Heritage Site.

Historic Masserie: Stay in a traditional masseria (fortified farmhouse), often restored into luxurious boutique hotels, where rustic charm meets modern elegance amidst olive groves and vineyards.

Olive oil: Puglia is the largest producer of olive oil in Italy and is known for its high quality and unique flavor.

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Sicily

Sicily, an enchanting island at the crossroads of the Mediterranean, offers an illustrious winemaking heritage within its own unique wine region. Sicilian wines are a testament to the island's diverse terroir, benefitting from the sun-drenched climate, fertile volcanic soil of Mount Etna, and varied topography that ranges from rolling hills to coastal plains. 

This unique environment fosters the production of grape varieties and distinctive wines that are as complex and varied as the island itself. From vibrant whites made with native grapes like Grillo and Catarratto to robust reds from Nero d'Avola and Frappato, Sicilian wines invite connoisseurs and casual drinkers alike into a world of flavor that encapsulates the essence of Sicily’s rich history and winemaking tradition.

Highlights

Mount Etna: Mount Etna is an active volcano located on the eastern coast of Sicily. It is the highest and most active volcano in Europe and has erupted several times throughout history.

Taste the essence of Sicily: Sicilian cuisine is known for its fresh seafood, citrus fruits, and sweet pastries. Some of the region's most famous dishes include pasta alla Norma, arancini, and cannoli. Add a cooking class to your time in Sicily to immerse yourself in the local culture. 

Relax at the beach: Sicily is home to some of Italy's most beautiful beaches, with crystal-clear waters and white sand. Popular beaches include San Vito Lo Capo, Mondello, and Taormina.

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Farmhouse Cooking Class

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Learn the secrets to true Italian cooking with passionate locals in the heart of Chianti. Don your apron and take part in a hands-on cooking class to introduce you to authentic and traditional home-style Italian Cooking.

The cooking classes take place in a charming farmhouse in the countryside, surrounded by olive groves and vineyards. The property produces its own Extra Virgin Olive Oil, organic fruit and vegetables. Afterwards, sit down to lunch accompanied by the Chianti Classico which best complements Tuscan cuisine.

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Private Visit at Castello di Ama

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Constructed in 2021, the "Arca" building houses the winery's heritage collection of historic vintages, consisting of about 80,000 Bordeaux-bottles and over 10,000 large formats. The ground floor serves as the reception room for visitors, who can enjoy a selection of wines by the glass while taking in the view of the vineyards from the courtyards and open spaces. 

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Tour Castello di Brolio

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The Gran Cru Tour at Castello di Brolio takes visitors through the castle's history and the unique Ricasoli estate vineyards, followed by a tasting of top wines in a private room and a Tuscan cuisine lunch at the Osteria di Brolio restaurant in a wooded park.

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Visit Belmond Castello di Casole

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Experience aristocratic rural life paired with contemporary style, surrounded by rolling hills and sprawling vineyards. Castello di Casole is one of those magical places where time stands still. 

Spread across 4,200 acres, this 10th-century estate is the perfect place to experience the wonders of rural Italy. While away the hours visiting local farms, spotting wildlife, or hunting for rare truffles. Then retreat to a world of comfort, elegance, and world-class dining. A warm welcome is guaranteed.

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Castello di Barolo

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Visit Castello di Barolo, located in the town of Barolo, and admire their contemporary art collection which features works by both Italian and international artists, with a focus on contemporary art from the 20th and 21st centuries.

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Wine Discovery

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Barolo DOCG is a renowned Italian wine region known for its exceptional terroir, producing rich, complex wines. Taste wines from top producers like Prunotto, Paolo Scavino, Aurelio Settimo, Elio Grasso, and Azienda Agricola Sukula while enjoying the views.

The Barbaresco region, northeast of Alba, produces rich and elegant wines. Visit family-run estates like Albino Rocca, Moccagatta, Bruno Rocca, Paitin, and Ca'del Baio. Take in the stunning landscapes and learn about their traditional winemaking methods.


For a more unique experience, venture to the Langhe region and discover lesser-known wineries producing top-quality wines. The Dolcetto, Barbera, and Nebbiolo grape varieties thrive in this area and are sure to impress with their distinct flavors.

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Relais San Maurizio

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This five-star hotel is located in a beautifully restored 17th-century monastery in the heart of the Langhe region. The hotel offers a spa, a Michelin-starred restaurant, and stunning views of the surrounding vineyards.

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Castello di Guarene

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Castello di Guarene is a five-star luxury hotel located in a beautifully restored 18th-century castle in the Roero region of Piedmont. The hotel features spacious rooms and suites, a spa, an outdoor pool, and a gourmet restaurant, all set amidst picturesque vineyards and countryside. 

The hotel is surrounded by vineyards, and guests can enjoy wine tastings and tours of the surrounding wineries. The hotel also has a restaurant that serves local cuisine and wine, including many of the region's famous wines such as Roero Arneis, Roero and Barbaresco.

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Hotel Danieli

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Facing the Venetian lagoon and just steps from San Marco, Hotel Danieli, Venice is a 5-star property with elegant and spacious accommodations, while the rooftop restaurant, Terrazza Danieli offers spectacular lagoon views. The historic hotel showcases majestic Venetian architecture that dates back as far as the 14th Century.

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Visit Verona

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Verona is a beautiful city with a rich history and culture, famous for its well-preserved Roman arena, Juliet's balcony, and charming old town. It's a great place to visit for art, architecture, and history lovers, as well as foodies who want to taste traditional Veronese dishes and access the fine wines of the Valpolicella.

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Experience Alto Adige

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Also known as South Tyrol, Alto Adige is known for its high-altitude vineyards and Alpine scenery. It's a great place to visit for wine enthusiasts who want to taste unique varietals such as Lagrein and Gewürztraminer and to enjoy outdoor activities such as walking and hiking amidst stunning mountain views. 

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Visit Top Amarone Producers

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Allegrini: One of the most famous and respected wine producers in the region, Allegrini produces award-winning Amarone wines, as well as Valpolicella and Ripasso wines.

Tommasi: Tommasi is another well-known producer of Amarone, as well as Valpolicella, Bardolino, and other varietals.

Zenato: Zenato is a family-run winery that produces a range of high-quality wines, including the popular Amarone della Valpolicella.

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Visit Lecce

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Known as the "Florence of the South," Lecce is a charming city with beautiful Baroque architecture and a lively arts scene. Visitors can explore the narrow streets and discover hidden gems, such as local artisan shops and traditional restaurants serving up delicious Puglian cuisine. Be sure to try specialties like orecchiette pasta, burrata cheese, and grilled octopus.

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Trulli of Alberobello

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Explore a UNESCO World Heritage Site by visiting the Trulli of Alberobello, where you'll find traditional cone-shaped houses unique to the Puglia region. Alternatively, discover the historic town of Matera, renowned for its ancient "Sassi" or cave dwellings.

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Local Cuisine Cooking Class

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Puglia is known for its delicious food, including fresh seafood, handmade pasta, and local wines. Learn how to make traditional Puglian dishes like orecchiette pasta, stuffed peppers, and pasticciotto pastries. You'll have the opportunity to shop for ingredients at a local market and then cook and enjoy your own meal under the guidance of a local chef.

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Wine Experiences

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Private wine tours and tastings include some of the premium wine properties such as;

Gianfranco Fino Winery in Manduria, is a renowned winery specializing in Primitivo grape varieties. With award-winning wines and personalized tours, it's a picturesque destination for wine enthusiasts.

Cosimo Taurino Winery, located in Salice Salentino, produces high-quality wines using traditional techniques. Its 16th-century cellar and stunning surroundings make it a perfect spot for an authentic wine-tasting tours.

Cantele Winery in Guagnano, offers award-winning, sustainable wines. With personalized tours in a beautiful location, it's an ideal choice for environmentally-conscious wine lovers.

Masseria Li Veli Winery, in a restored 19th-century farmhouse, is situated in Puglia's scenic countryside. Known for its high-quality wines, on-site restaurant, and sustainable practices, it offers tastings, tours, and hosts events year-round.

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Explore Mount Etna

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Embark on an excursion to Mount Etna, Europe's tallest active volcano. Explore its lunar landscapes, hike its trails, and visit local vineyards nestled on its slopes.

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Taste Marsala Wines

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Florio Winery: Visit the renowned Florio Winery in Marsala, which has a rich history of producing Marsala wine. Take a guided tour of their historic cellars, learn about the traditional methods of making Marsala wine, and indulge in tastings of their various wine styles, including sweet, dry, and aged Marsala.

Cantine Pellegrino: Explore Cantine Pellegrino, a historic winery in Marsala that has been producing wine for over a century. Take a guided tour of their cellars, learn about the wine production process, and sample a range of their Marsala wines, including their renowned Marsala Superiore and Marsala Vergine.

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Hotel Villa Athena

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Experience the Valley of the Temples with a stay at Hotel Villa Athena, a luxury hotel offering elegant rooms, a pool, and a restaurant with panoramic views. The hotel offers easy access to the magnificent archaeological site, featuring well-preserved ancient Greek temples and ruins.

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La Foresteria Planeta Estate

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Part of the Planeta winery, this boutique hotel immerses guests in the world of wine. It offers wine tastings, vineyard tours, and a gastronomic experience featuring Sicilian cuisine paired with their renowned wines. Planeta is one of the most prominent wineries in Sicily, known for its exceptional wines and beautiful estates. They offer tours, tastings, and immersive experiences at their various locations, including Menfi, Vittoria, Noto, and Etna.

Custom Travel Itineraries

At Into The Vineyard, we pride ourselves on our ability to offer you complete freedom to build your perfect trip. Start with one of our many sample itineraries and customize as you desire, or start with a blank page, and with the help of our expert Trip Planners, we can create your dream wine-inspired travel experience. 

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