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Italy

italy

Overseas Adventure Travel, the leader in personalized small group adventures, has been changing lives through travel since 1978. Our 6 Italy Small Group Adventures and 10 Italy Small Ship Adventures will take your small group into the heart of a destination to venture where the big tour groups can’t. No matter which adventure you choose, O.A.T. always offers:

  • The freedom to personalize your experience, with options to arrive early, add pre- or post-trip extensions, stopover in popular cities, and more.
  • Small group of no more than 25 travelers, allowing us to take you off the beaten path and immerse you in local culture.
  • Adventures tailored to the solo traveler, with FREE or low-cost Single Supplements and 23,000 single spaces being offered in 2024.
  • Expert Trip Experience Leaders, residents of the region you visit who will share their insights and bring your destination to life.

However you'd like to experience Italy, O.A.T. has an adventure for you. We explore every corner of this legendary peninsula, from the Dolomites in northern Italy to sun-drenched Puglia and Sicily, the “soccer ball” off the toe of Italy’s “boot.” Iconic cities like Florence, Venice, and Rome dazzle visitors with their ancient history, prestigious art galleries, and delicious food, while quaint coastal fishing villages, deep blue northern lakes, and the rolling hills in Tuscany are a cool salve for a weary soul. You can experience all of this and more when you journey to Italy with O.A.T.

Compare Our Adventures

Click 'Select to Compare' to see a side-by-side comparison of up to adventures below—including
activity level, pricing, traveler excellence rating, trip highlights, and more

Spend 11 days in Italy on

New! Italy’s Coastal Charms: Naples, Ischia Island & the Amalfi Coast

O.A.T. Adventure by Land

DAYS 13
FROM $5,595
PER DAY $431

Spend 9 days in Italy on

New! Amalfi Coast: Naples, Sorrento & Pompeii

O.A.T. Adventure by Small Ship

DAYS 11
FROM $5,795
PER DAY $527

Spend 16 days in Italy on

New! Jewels of the Sicilian Coast: Palermo, Siracusa & Mount Etna

O.A.T. Adventure by Small Ship

DAYS 16
FROM $6,095
PER DAY $381

Spend 15 days in Italy on

Sicily's Ancient Landscapes & Timeless Traditions

O.A.T. Adventure by Land

DAYS 16
FROM $4,595
PER DAY $288

Spend 15 days in Italy on

Northern Italy: The Alps, Dolomites & Lombardy

O.A.T. Adventure by Land

DAYS 16
FROM $5,595
PER DAY $350

Spend 14 days in Italy on

Tuscany & Umbria: Rustic Beauty in the Italian Heartland

O.A.T. Adventure by Land

DAYS 15
FROM $4,595
PER DAY $307

Spend 13 days in Italy on

Italy’s Western Coast & Islands: A Voyage from Rome to Valletta

O.A.T. Adventure by Small Ship

DAYS 17
FROM $9,295
PER DAY $547

Spend 13 days in Italy on

Undiscovered Adriatic: Eastern Italy, Venice, Puglia & Malta

O.A.T. Adventure by Small Ship

DAYS 18
FROM $9,495
PER DAY $528

Spend 25 days in Italy on

Italian Coastal Odyssey: Hidden Italy, Sicily & Malta

O.A.T. Adventure by Small Ship

DAYS 29
FROM $16,595
PER DAY $573

Spend 10 days in Italy on

French & Italian Rivieras: Avignon, Corsica, Elba & Rome

O.A.T. Adventure by Small Ship

DAYS 17
FROM $8,795
PER DAY $518

Spend 1 days in Italy on

New! Mediterranean Navigation: Malta, Sicily, Tunisia, Algeria, Morocco & Coastal Spain

O.A.T. Adventure by Small Ship

DAYS 18
FROM $10,595
PER DAY $589

Spend 9 days in Italy on

New! Alpine Europe: France, Italy's Dolomites, Switzerland & Austria

O.A.T. Adventure by Land

DAYS 18
FROM $7,195
PER DAY $400

Spend 17 days in Italy on

New! Journey Through Southern Italy: Sicily, the Aeolian Islands, Calabria & Puglia

O.A.T. Adventure by Land

DAYS 18
FROM $6,795
PER DAY $378

Spend 7 days in Italy on

New! Allure of the Adriatic: Italy, Slovenia & Croatia

O.A.T. Adventure by Small Ship

DAYS 17
FROM $3,495
PER DAY $206

Spend 8 days in Italy on

Mediterranean Cultures & Islands: A Voyage from Spain to Greece

O.A.T. Adventure by Small Ship

DAYS 19
FROM $8,095
PER DAY $427

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Find the Adventure That’s Right for You

Our Activity Level rating system ranks adventures on a scale of 1 to 5 to help you determine if a trip is right for you. See the descriptions below for more information about the physical requirements associated with each rating.

Activity Level 1:

1 2 3 4 5

Easy

Travelers should be able to climb 25 stairs consecutively, plus walk at least 1-2 miles over some uneven surfaces without difficulty. Walks typically last at least 1-2 hours at a time. Altitude can range from zero to 5,000 feet.

Activity Level 2:

1 2 3 4 5

Moderately Easy

Travelers should be able to climb 40 stairs consecutively, plus walk at least 2-3 miles over some uneven surfaces without difficulty. Walks typically last for at least 2-3 hours at a time. Altitude can range from zero to 5,000 feet.

Activity Level 3:

1 2 3 4 5

Moderate

Travelers should be able to climb 60 stairs consecutively, plus walk at least 3 miles over some steep slopes and loose or uneven surfaces without difficulty. Walks typically last for 3 or more hours at a time. Altitude can range from 5,000 to 7,000 feet.

Activity Level 4:

1 2 3 4 5

Moderately Strenuous

Travelers should be able to climb 80 stairs consecutively, plus walk at least 4 miles over some steep slopes and loose or uneven surfaces without difficulty. Walks typically last for 4 or more hours at a time. Altitude can range from 7,000 to 9,000 feet. Expect three or more one-night stays in some locations, and very limited free time for rest or independent exploration.

Activity Level 5:

1 2 3 4 5

Strenuous

Travelers should be able to climb 100 or more stairs consecutively, plus walk at least 8 miles over some steep slopes and loose or uneven surfaces without difficulty. Walks typically last for 4 or more hours at a time. Altitude can range from 10,000 feet or more.

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Italy: Month-By-Month

There are pros and cons to visiting a destination during any time of the year. Find out what you can expect during your ideal travel time, from weather and climate, to holidays, festivals, and more.

Italy in January & February

Winter in Italy means smaller crowds and cooler temperatures—both prime reasons to visit this time of year. In fact, the weather throughout most of Italy is actually quite mild and comfortable during January and February. If you’re looking for more traditional winter weather, the north provides with its lower temperatures and snow-capped mountains. Locals and visitors alike can enjoy wintry activities from ice-skating rinks that pop up in the piazzas to skiing in the legendary Alps.

With fewer tourists to compete with, your travel dollar will go further. Of course, that also can mean some attractions will keep shorter hours in winter or close all together—so it’s best to check ahead of time. 

Holidays & Events

  • January 6: The Epiphany
  • Mid-January: Feast Day of San Antonio Abate
  • January 20: Feast Day of San Sebastiano
  • Carnevale: Numerous festivals are celebrated throughout the two weeks prior to Lent

Must See

Carnevale (Carnival) festivals are held all across the country, but Venice is the place to be during this two-week party. During Carnivale, the City of Canals is transformed into a magical mélange of masquerade balls, pageants, gondola parades, and throngs of masked revelers filling the streets. You should expect a crowd during your visit, and access to some attractions may be limited. But the main attraction is the city itself—awash in color, confetti, and celebration.

If you’re craving a quieter celebration, head to Sicily. Every year on the first Sunday of February, the Valley of the Temples in Agrigento hosts an annual almond blossom festival with parades, traditional dances, and exhibits featuring local artisans’ crafts. The almond blossom is considered a harbinger of spring in Sicily, so expect a joyous, jubilant experience.

Italy in March

Much like the beginning of spring in the States, March in Italy is a mix of sunshine, rain showers, and milder temperatures—perfect weather for exploring. The primarily Roman Catholic country is also gearing up for Easter this month, so expect sites, hotels, and attractions to awake from their winter hibernation and offer full hours again for the spike of visitors expected.

Depending on when Easter falls during your visit, religious celebrations will be held all across Italy in the days leading up to and during the holidays. This is an excellent opportunity to experience local culture and traditions up close and personal.

Holidays & Events

  • March 8: La Festa della Donna, more widely known as International Women’s Day, is celebrated throughout Italy with flowers, wine, and decadent mimosa cakes
  • The Rome Marathon: Held on the third Sunday of March each year

Must See

Should you visit Rome during Easter Week, there is no shortage of celebrations. The Pope is your host, leading numerous religious events including a Palm Sunday Mass in Saint Peter’s Square and the solemn Stations of the Cross procession, held on Good Friday at Rome’s iconic Colosseum. 

Italy in April

Avoid the summer crowds—and its climbing temperatures—when you visit Italy in April. Balmy spring weather and plentiful sunshine make a visit here this time of year a pleasure. Tuscany’s countryside is especially beautiful under its new blanket of wildflowers. All sites and attractions are officially open, but you won’t need to share space with as many visitors.

April also ushers in myriad spring celebrations—from tulip festivals in Umbria to spectacular artichoke festivals, some featuring magnificent sculptures created entirely of artichokes. 

Holidays & Events

  • April 25: Liberation Day; a national holiday that marks the anniversary of the fall of Mussolini

Must See

If you visit Venice on April 25, be sure to bring a rose with you. Venetians celebrate the Festa di San Marco (Saint Mark)—patron saint of the city and the namesake for its most famous square. This day is also referred to as the Rosebud Festival during which men offer a single red rose to the woman in their lives as a symbol of love. 

Italy in May

One of the most ideal times of year to visit—Italy in May offers sunshine, warm (but not too hot) temperatures, and the last month of quiet before the summer crowds descend. Also known as the “month of the rose,” May gardens are at their peak—which makes outdoor explorations extra scenic. 

Holidays & Events

  • May 1: Labor Day; similar to our Labor Day celebrations, Italians reserve the first of May to recognize workers’ achievements in fighting for their rights by taking a day off to eat, socialize, and dance with family and friends
  • May 1: The Sant Efisio procession, a four-day celebration and Sardinia’s most important festival

Must See

Near Piazzale Michelangelo in Florence, the Giardino dell’Iris, or Iris Garden, is open to the public for just a few precious weeks in May. Home to more than 1500 species of irises—including 15 rare varietals near extinction—the garden is a flower-lover's and photographer’s dream. 

Italy in June-August

Summer in Italy ushers in the country’s famously hot weather—temperatures can even rise above 100⁰F in the south. These summery conditions send locals and visitors alike to Italy’s beaches and attract tourists to the cities. This time of year is also the most expensive time to travel in Italy, so it’s best to plan your visit in advance.

Summer is also prime season for cultural and folkloric festivals—travelers can find everything from jousting tournaments in medieval hill towns, to free outdoor movies projected against the walls of Roman ruins, music concerts held in the ancient Greek theaters of Sicily, and more.

Holidays & Events

  • June 2: Republic Day is a national holiday commemorating the day the country voted to abolish the monarchy and become a republic and is traditionally celebrated with parades
  • June 24: The Feast Day of San Giovanni is celebrated in Florence with spectacular fireworks shows and an annual Florentine soccer game
  • August 15: Assumption Day is celebrated in honor of Jesus’s mother Mary with processions, fireworks, and even a horse race around Sienna’s famous medieval piazza.

Italy in September

September days remain warm in Italy, but the nights begin to cool down to more comfortable temperatures. Italians have returned to work and school, but that doesn’t lead to a decrease in celebrations. September marks the beginning of harvest season, punctuated by myriad festivals dedicated to everything from prosciutto to olives. La Vendemmia, Italy’s grape harvest, begins towards the end of September, which means wine festivals are plentiful as well. 

Must See

If you visit Venice on the first Sunday of September, you will find yourself in the midst of the city’s Regata Storica—a unique gondola race that has plied the canals of Venice for thousands of years. The storied event kicks off with true Venetian pageantry: a spectacular parade of 16th century-style boats and gondoliers in period costumes. 

Italy in October & November

Fall in Italy heralds the last of the summer heat, a lessening of crowds, and food festivals aplenty. Mushrooms, chestnuts, olives, grapes, and white truffles are all in season and widely celebrated across the countryside. The decrease in crowds and temperatures also make visiting the cities a more comfortable affair. 

Holidays & Events

  • White truffle fair and market: Takes place every weekend from early October through mid-November in Alba, a town in Italy’s Piedmont region
  • November 1: All Saints’ Day is a day devoted to the dead; locals attend Mass and hold processions to cemeteries

Must See

One of the most important film festivals in the world, the Rome International Film Festival, takes place in the Eternal City throughout the month of October. The event attracts world-premiere films and cinema stars from all across the globe.

If you’re interested in something a bit sweeter, head to Perugia in October for its famous Eurochocolate Festival. The best time to attend is the first Sunday of the festival to view intricate sculptures carved from massive blocks of chocolate. 

Italy in December

Early winter in Italy is cooler, but still relatively mild—you’ll have to head north to get in some early-season skiing. The cities are quieter and easier to navigate, though hotels, attractions, and hiking sites outside major hubs are likely to be closed in the off-season. It’s best to call before your visit.

December also marks the beginning of the festive Christmas season. If you happen to be in Italy on Christmas Eve or Day, attending Mass in one of the country’s many beautiful, historic churches is a once-in-a-lifetime experience. 

Holidays & Events

  • Early December: The Feast of Saint Ambrose, the patron saint of Milan; and Feast of the Immaculate Conception
  • December 25: Christmas Day
  • December 26: Saint Stephen’s Day—while Christmas Day is traditionally celebrated at home, Italians reserve the day after for visiting local nativity scenes and churches, and generally filling the streets with well-wishes and cheer 

Must See

For a larger-than-life holiday experience, visit the towering Christmas tree and life-sized Nativity scene displayed in the Vatican’s St. Peter's Square.

December is not limited to Christmas celebrations, of course—in early December, Tuscany’s Wild Boar Festival attracts revelers and foodies to the medieval town of Suvereto.  

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Rome

Rome is a bustling metropolis, pulsing with life. Here, tiny gelaterias and contemporary cafes vie for their place along the Rome’s fast-paced and congested roadways. Meanwhile, the city’s old guard, composed of the Colosseum and Pantheon, remain stoically at their posts as they have for nearly 2,000 years. Since the age of Julius Caesar and the Roman Empire, countless pilgrims have walked its narrow and winding alleyways to see for themselves some of the most iconic sites to be described in history books, and depicted in film. From the Baroque Spanish Steps and the venerated St. Peter’s Basilica, to the dozens of museums overflowing with ancient artifacts and masterpieces by Michelangelo, Rome—the “Eternal City”—is a living museum. In fact, its entire historic district was named a UNESCO World Heritage Site.

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Venice

Venice is an enchanting city where an intricate web of canals replaces motorways, and entire buildings are lost within the lackadaisical incoming fog. Located roughly two and a half miles from mainland Italy, Venice is actually a cluster of 117 islands and islets joined together by more than 450 bridges. The most well-known, the Rialto, spans the city’s main waterway, the Grand Canal. This arched-stone bridge decorated with biblical images was completed in 1591. For centuries, it provided the only means of crossing the Grand Canal on foot. Instead, medieval Venetians would rely on small merchant skiffs and gondolas to go about their daily errands. Today, in the world’s only car-less pedestrian city, water buses, water taxis, and—of course—gondolas are relied upon to get around. In keeping with this 900-year-old tradition, visitors will only find Venice-born men at the helm of these long, sinewy vessels.

The bustling hub of this “Floating City” is St. Mark’s Square. Visitors come to see its namesake basilica and the Gothic-style Doge’s Palace which line this famed piazza. Not quite as popularized, by television and film, is Venice’s Jewish Ghetto. This was the first neighborhood of its kind, and has managed to remain an active community with five synagogues—no small feat in an overwhelmingly Catholic country.

Beyond the weaving labyrinth of streets, is another side of Venice, with quiet islands such as the peaceful, sparsely-populated Torcello and the colorful fishing village of Burano. In addition to incredibly fresh fish dishes like risotto de gò, the latter island is also known for lace and glassmaking.

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Florence

Florence—in the heart of Tuscany—is quite possibly the world’s greatest repository of art. Although up for discussion, Julius Caesar is largely credited with founding this highly-influential city in 59 B.C.

Regardless of its exact origins, Florence’s creative class has been the source of innumerable paintings, sculptures, and architectural styles for more than five centuries. The Renaissance period began here in the 1300s. Prominent galleries such as the Uffizi and the Pitti Palace feature the paintings of master artists, and are among the more than 80 museums found within the boundaries of this forward-thinking capital. Renowned writers and poets—Dante, Petrarch, and Boccaccio—have all called this city home. Entirely new forms of creative expression—like opera—were born in Florence.

Over the course of the next three centuries, this new, more humanist age, lead to advancements in the fields of optics, astronomy, and anatomy, through the work of Galileo and other scientists of the era. Florentine know-how also helped pull the whole of Europe out from the Dark Ages with the development of a standard European currency, the florin. The solid-gold coin functioned similarly to today’s euro.

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Sicily

Part of the Italian Republic, and yet … not. Sicily is a semi-autonomous region with its own parliament and president. Separated from the mainland by more than just legislative boundaries, and water, Italy’s largest region is culturally different as well. For centuries, conquerors from across the Mediterranean Sea fought for sovereignty over this strategically-significant island. It wasn’t until 1861, after a series of ancient Greek and Roman wars, followed by clashes between the Byzantines and Arabs, that the often-besieged island even became part of a newly-unified Italy.

As a result of regular political upheavals, the Sicily of today is an amalgam of cultures and ethnicities. Peruse the island’s prized outdoor markets and see how this rich history has played a part in shaping Sicilian cuisine. Vendors proudly display their fresh, locally-grown produce, and just-caught white fish—a key ingredient in any traditional Trapani-style couscous. Beyond the eclectic cuisine, the influence of other cultures can be seen across this nearly ten-thousand-square mile island.

Fingerprints of Sicily’s diverse past mark more than its humming marketplaces. In Siracusa, an archaeological park is dedicated to preserving and maintaining the Roman Amphitheater and Teatro Greco. The island’s capital, Palermo, was founded in 734 B.C. and is home to a varied collection of medieval structures that combine the Norman style of large-scale and rounded archways with traditional Islamic imagery of stars, moons and complex geometric patterns.

In addition to this island’s assortment of historic gems, it is also the site of Italy’s tallest mountain south of the Alps—Mount Etna. At 10, 991 feet high, this natural wonder is the largest active volcano in Europe. One of the best ways to experience Mount Etna’s power is to watch for fiery red eruptions under the cover of night.

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Sardinia

Off the coast of Italy, surrounded by the turquoise Mediterranean, the island of Sardinia has flourished for millennia—continuously populated from prehistoric times to today. Scores of civilizations have landed upon the island over the years, looking for safe passage, a new home, or a land to conquer. The list of these “visitors” includes the ancient Phoenicians, Carthaginians, and Romans; medieval Vandals; the Byzantine Empire; and even the Spanish and Austrians. It was only as recently as 1946 that Sardinia was folded into the rest of the Italian Peninsula under the Unification of Italy. Even so, Sardinia has fiercely retained its own language, culture, cuisine, and traditions.

Today, Sardinia’s visitors come first and foremost for its gorgeous beaches, blanketed with sugar-soft sand in shades of glistening white, gold, and even pink. It seems difficult to think of a reason to leave Sardinia’s stunning coastline, but in fact there are many. The rugged landscape is dotted with remnants of the island’s fascinating history. Thousands of nuraghi—mysterious Bronze Age stone ruins shaped like beehives—are scattered all over Sardinia. And as you delve deeper into the island’s rustic interior, you’ll encounter communities that seem untouched by time, such as the hearty people of the Barbagia, Sardinia’s remote and rustic heartland, where these insular locals stick to old traditions that can be traced back to prehistoric times.

From its ancient beginnings to its modern-day status as a beach-lover’s playground, Sardinia continues to beckon visitors to its tantalizing shores.

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Puglia

Nestled down by the heel of Italy’s boot, the sun-drenched region of Puglia offers travelers the laid-back atmosphere of a small town, while still claiming the longest coastline on the Italian Peninsula. Best known for its white-washed hill towns, centuries-old farmlands, and ruggedly beautiful shores along the Mediterranean Sea, Puglia is also rich in culture and history.

First colonized by the ancient Mycenaean Greeks, Puglia eventually became part of the Kingdom of Naples after 1282, until the unification of Italy in the 1860s. Signs of its long history can be found throughout the region—from the ancient stone houses of worship of Sassi di Matera and the conical-roofed trulli homes of Alberobello, whose limestone architecture dates back to the mid-14th century, to the elegant Baroque-influenced architecture found in the seaside town of Lecce.

A region few American travelers have experienced before, Puglia remains an unspoiled region full of discoveries.

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Bressanone

Locked away in South Tyrol—a region characterized by picturesque villages, medieval castles, and jagged mountains— Bressanone seems in many ways like a quiet Austrian town staged amid the striking Italian Alps. Walking the medieval streets you will hear Italian, German, and Ladin—a Romance language specific to the Dolomite region—a testament to the cultural crossroads the region has been for centuries.

The highlight of the town is the Duomo Di Bressanone, also known as the Cathedral of Santa Maria Assunta and San Cassiano. Constructed in the tenth century, it burned down and was later reconstructed in a quintessential Romanesque style, dressed with ornate southern European architecture and a reserved façade. Among the cathedral’s many breathtaking frescos, “Christ Welcomes May into Heaven,” is an image so detailed it leaves an indelible and enduring impression on the memory.

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Verona

A former Roman settlement, Verona is a compact Italian city not far from Milan and Venice that is noted for its elegant churches, magnificent red- and white-striped Duomo, and picturesque core of cobblestone streets lined with medieval buildings. Verona, of course, is also renowned for its association with the star-crossed lovers, Romeo and Juliet. Yet Shakespeare actually had two more plays set in this romantic canal-laced city nestled along the banks of the Adige River—The Taming of the Shrew and The Two Gentlemen of Verona.

While Verona is filled with charming palaces, merchants’ houses, and bustling gathering spots such as Piazza delle Erbe, its most famous square, the primary reason that Verona has been designated a UNESCO World Heritage Site is for its wealth of Roman ruins—in fact, tiny Verona claims to have more Roman ruins than any Italian city other than Rome itself. Verona’s landmark architectural wonder is its vast Roman amphitheater. Constructed outside the city walls in about AD 30, the impressive structure could accommodate some 30,000 spectators. In 1913, as it celebrated the birth of Giuseppe Verdi, Verona’s Roman arena became the world’s largest open-air opera venue. Even today, a highlight of the summer opera season is witnessing a performance here, at one of the best preserved Roman amphitheaters in all of Italy.

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Northern Italy

Since the late 1950s, when Milan's acclaimed fashion houses like Versace and Valentino send their hand-painted leather and neoprene works of art down the runway, the world sits up and takes notice.

For those searching for more than haute couture, Northern Italy’s most heavily populated city offers a number architectural standouts as well. Milan's massive marble cathedral is highly decorated and boasts over 135 spires. Teatro alla Scala shines with red and gold ornamentation, while tucked away on the wall of a refectory, under museum lighting stands Leonardo da Vinci’s revered The Last Supper mural.

When the city’s fashion elite and busy day traders—the Italian Stock Exchange is in Milan—need to unwind they head north to the mountain-bound lakes district. Wealthy Italians, international celebrities like George Clooney, and regular people craving the serene, deep blue waters of Lake Como have been coming to the area since the Roman age. In addition to lakeside villas and lush, green landscapes, the town of Como is also known for its 4,000-year-old silk industry.

The Lakes District isn't the only part of Northern Italy with a UNESCO World Heritage Site (Ossuccio Mountain situated above Lake Como was designated in 2003). To the southwest is another historic locale recognized for its traditional wine making: the Langhe wine valley. Long-low hills, standout vintages, and white-truffle-topped pastas are staples of this sub-region of Piedmont.

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