Milan Tours in Winter
Planning for a trip to Milan during Winter? We offer 80+ tour packages to Milan departing in Winter that have 660+ customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Milan on your Winter holiday.
See all Milan Winter Tours
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10 Best Winter Tours in Milan
Join one of these handpicked Milan Winter tour packages, tailored to the season.
Italy’s finest cities await on the 'Treasures of Italy' tour, a 13-day sightseeing journey designed especially for seniors who appreciate comfort and culture. Starting and ending in Rome, you’ll travel through Florence, Milan, Siena, and more, enjoying curated experiences and rich history at every turn. All hotels, transportation, and meals are included, letting you focus on the scenery and stories. The true highlight of this trip is its comprehensive itinerary, offering seniors an easy-paced yet thorough exploration of Italy’s artistic and architectural masterpieces.
13 days
fromUSD 1,901
Set off from Rome on the 'Italy and Switzerland' tour, a 9-day sightseeing journey through Italy’s capital and beyond. With hotels, transportation, and meals all included, this guided group trip lets you discover the best of Italy in a relaxed, senior-friendly manner. The highlight of this tour is its cross-border perspective—offering a taste of Swiss culture alongside Italian classics, all without the challenges of a demanding itinerary. It’s an easy, enriching escape for those eager to broaden their horizons.
9 days
fromUSD 1,487
5% Off Today
Immerse yourself in Italy’s timeless magic with the "Italian Scene" tour, a 10-day countryside and village trip starting and ending in Rome. Discover Florence’s artistic pulse, Venice’s romantic canals, and the sun-drenched Italian Lakes, all at a gentle, easy pace perfect for families and seniors. Visit Sorrento’s citrus groves, capture memories at Pisa’s famed Leaning Tower, and honor Assisi’s spiritual calm. With expert guides, seamless transport, and comfortable hotels, this group tour makes each moment count. Its unique draw? The harmonious blend of Italy’s greatest cities and its picturesque rural heartlands, all wrapped into one unforgettable tour package.
10 days
USD 1,950fromUSD 1,853
From Milan’s chic avenues to Rome’s ancient grandeur, the 'All About Italy' tour is an 8-day sightseeing journey perfectly suited for seniors. This guided group trip covers both cities at a comfortable pace, with accommodation, transport, and meals all provided. What makes this tour stand out is its focus on Italy’s most iconic urban gems, offering a well-rounded Italian adventure that combines ease, culture, and memorable moments.
8 days
fromUSD 1,326
Experience Italy’s artistic splendor on the 'Discover Italy end Milan' tour, a 7-day sightseeing journey from Rome to Milan. Tailored for seniors, this group package includes hotel stays, transportation, and meals, ensuring a relaxed and enjoyable exploration. The standout feature of this trip is its focus on two of Italy’s most celebrated cities, providing a carefully paced itinerary that lets you savor the sights and flavors without feeling rushed.
7 days
fromUSD 948
15% Off Today
Experience Milan at its most captivating on this four-day self-guided art and architecture trip, tailored for seniors who relish cultural discovery at an unhurried pace. Explore Sforza Castle—Europe’s most impressive urban fortress—and the awe-inspiring Duomo Cathedral. Admire Leonardo da Vinci’s Last Supper, stroll the trendy Navigli district, and take a day trip to Lake Como and Lugano. With shopping opportunities in one of the world’s fashion capitals, this tour’s unique selling point is its seamless blend of history, art, and modern style, all within Italy’s vibrant northern hub.
4 days
USD 814fromUSD 692
21% Off Today
Travel from the shores of Venice to the ancient city of Rome on this 8-day guided tour of Italy. Begin your journey in Milan, where a festive feast complete with decadent Italian wines await you. In Venice, relax on a private boat as you pass by the iconic city to St Mark's Square, where you will see a gilded basilica anchoring the bustling piazza. Embark on a traditional gondola ride with your skilled Venetian gondolier, gliding along the canals while enjoying music. See the legendary Colosseum in Rome, then travel to the Vatican Museums, where a Local Expert will lead you through the papal art collection and to Michelangelo’s Sistine Chapel. Celebrate a fantastic trip over dinner in a local restaurant.
8 days
USD 3,395fromUSD 2,667
Journey through Italy’s timeless wonders with the 'Amazing Italy' tour—a 15-day city sightseeing trip that brings together the country’s most celebrated destinations. Designed for travelers who crave a relaxed yet immersive experience, this guided group tour blends classic landmarks, art, and natural beauty into a seamless adventure.
Your Italian escapade launches in Rome, where ancient history and vibrant street life converge. Step back in time as you explore the iconic Colosseum, marvel at the grandeur of St. Peter’s Basilica in Vatican City, and stroll through the eternal city’s piazzas. The rolling hills and renowned wineries of Tuscany await, with stops in Monteriggioni and San Gimignano before arriving in Florence—the cradle of the Renaissance.
Continue your journey by admiring the Leaning Tower of Pisa, then take in the dramatic cliffside villages of Cinque Terre along the Italian Riviera. In Venice, glide through enchanting canals, and in Naples, discover Europe’s greatest architectural treasures. The adventure extends to the Blue Grotto of Capri before uncovering the mysteries of ancient Pompeii, preserved beneath Mount Vesuvius’s ashes.
The tour’s unique selling point lies in its artful balance: a comprehensive itinerary with ample time to savor each destination, guided by local experts. With comfortable accommodations, inclusive transport, and select meals, this trip is perfect for discerning travelers longing for a rich, leisurely exploration of Italy’s greatest marvels.
15 days
fromUSD 2,624
8% Off Today
Italy’s timeless beauty unfolds on the Simply Italy tour, a 15-day journey designed for young adults seeking pure immersion in the country’s rich history and vibrant culture. Wander through Rome’s ancient streets, marvel at Florence’s Renaissance art, and glide along Venice’s romantic canals. Venture to Cinque Terre’s rugged coastlines, savor authentic pasta in the Amalfi Coast, and bask in the sun-drenched charms of Sorrento and Positano.
Every day blends historical discovery with irresistible cuisine and local color. This is the trip for those who crave the good life: art, architecture, food, and the Mediterranean spirit. With all logistics handled, your focus stays on soaking up la dolce vita at every turn.
What sets this tour apart is its all-encompassing itinerary—the best of Italy, from city icons to hidden coastal gems, in a single, unforgettable package.
15 days
USD 2,729fromUSD 2,515
8% Off Today
Savor every flavor of Italy with the "Italian Espresso" cultural tour—a 10-day journey for young adults who crave both the classics and the hidden gems. Starting and ending in Rome, you’ll wind through Venice’s canals, Florence’s Renaissance art, and the colorful villages of Cinque Terre. Along the way, indulge in antipasto, Chianti, and local trattorias, while exploring architectural marvels in Pisa, Verona, and Siena. The tour’s unique touch? A seamless blend of culinary delights and world-famous landmarks, all enjoyed with the comfort of included hotels, meals, and expert guidance.
10 days
USD 2,005fromUSD 1,848
See all Milan Winter Tours
Top Milan Tour Activities for Winter
From city sightseeing tours to art and architecture and others, here are some popular tour activities in Milan with departures in Winter.
Milan Winter Tours for all Age Groups
Milan tours in Winter designed for all ages—families, young adventurers, seniors, and everyone in between.
Trending Milan Winter Tour Deals
Popular Milan Winter multiday tours now available at reduced prices, on sale for a limited time.
21% Off Today
Travel from the shores of Venice to the ancient city of Rome on this 8-day guided tour of Italy. Begin your journey in Milan, where a festive feast complete with decadent Italian wines await you. In Venice, relax on a private boat as you pass by the iconic city to St Mark's Square, where you will see a gilded basilica anchoring the bustling piazza. Embark on a traditional gondola ride with your skilled Venetian gondolier, gliding along the canals while enjoying music. See the legendary Colosseum in Rome, then travel to the Vatican Museums, where a Local Expert will lead you through the papal art collection and to Michelangelo’s Sistine Chapel. Celebrate a fantastic trip over dinner in a local restaurant.
8 days
USD 3,395fromUSD 2,667
15% Off Today
Join this four-day short break in Milan and discover Sforza Castle the most impressive urban castle in Europe, and Duomo Cathedral, a striking example of Gothic art and the largest church in Italy. Admire the famous Last Supper of Leonardo Da Vinci, enjoy the Navigli district and take a trip to Lake Como and Lugano. Don’t miss the shopping opportunity as Milan is one of the most important cities in the world of fashion.
4 days
USD 814fromUSD 692
15% Off Today
An exciting tour through the alluring sites of the North of Italy visiting the main points of interest famous worldwide such as Venice, Verona, Como and Milan. From the Main Squares and historic cradle of the towns, you will be led across the highlights of each city.
8 days
USD 2,623fromUSD 2,230
8% Off Today
Welcome to 15 days of pure Italian travel immersion. Covering Rome, Florence, Milan, Venice and beyond, this one brings you the blissful best of this soul-stirring country. Explore Rome's historical highlights, travel through the streets of Michelangelo's Florence, indulge in some authentic pasta on the Amalfi Coast. Stop by to see the stooping slopes of Sorrento or the picture perfect Positano for your summery soul. And that's just an aperitivo. Beauty, romance and all the pasta you can fit in; the good life just got even better. That's amore!
15 days
USD 2,729fromUSD 2,515
15% Off Today
Drive through some of Italy's most iconic locations on this six-day tour that takes you through Florence, Siena, Verona, Venice, Sirmione and Milan. Considered the birthplace of the Renaissance, Florence breathes history at every corner, while Venice will enchant you with its shimmering canals.
6 days
USD 2,765fromUSD 2,350
8% Off Today
10 days of la dolce vita, pronto. This one is pure Italian travel, covering all the big bucket-list destinations of Venice, Florence & Rome, plus the smaller charms of Pisa, Verona, and Siena. We'll ooh and aah over antipasto & chianti, dine on regional specialities in local trattorias, boat through the canals and islands of Venice, and explore the architecturally magnificent city of Florence. Expect comfy hotels and plenty of world-famous espresso & pizza on the way.
10 days
USD 2,005fromUSD 1,848
15% Off Today
Discover some of Italy’s most important cities on this eight-day tour beginning in the Eternal City of Rome and ending in the fashion capital of Milan. On the way, explore the artistic and cultural heritage of Florence and Venice with its shimmering canals as well as the cities of Verona and Siena.
8 days
USD 3,344fromUSD 2,843
15% Off Today
Join our seven days tour for a “full immersion” into Leonardo Da Vinci’s life. Visit Accademia Gallery in Venice, Cenacolo and Pinacoteca Ambrosiana in Milan and Uffizi Gallery in Florence. Our expert guides will lead you to the most important sites of these cities to show you the famous masterpieces of this amazing artist and his life.
7 days
USD 1,972fromUSD 1,676
10% Off Today
The perfect mix of group activities and all-important YOU time.
Great expectations? You should have. This immense wintery adventure around Europe’s most enchanting cites and spellbinding landscapes is the REAL fairytale. Discover the legendary capitals of Paris, Rome, Berlin and Amsterdam. Mix in the myths of Eastern Europe. And sprinkle the snow-capped peaks of the Swiss AND Austrian Alps on top. This trip is pure magic. Trust us.
29 days
USD 6,269fromUSD 5,642
25% Off Today
Looking for a winter escape? Expat Explore’s unforgettable Italy tour packages await! Uncover Northern Italy's ancient history, rich culture and mouthwatering cuisine during low season. Explore the epic sights of Rome, Florence and Venice - the art cities of Italy. Tuck into famous local foods in Parma, Bologna and Tuscany. Discover hidden gems like Ferrara, the UNESCO-listed city and the awe-inspiring Trento, located in the Dolomite Mountains. Marvel at the majestic Italian Lake District, pose with the Leaning Tower of Pisa and style it up in Milan on this affordable tour!
10 days
USD 1,720fromUSD 1,287
Milan Winter Tour Types
Discover Milan Winter tours in your way! Choose from group tours, private experiences, solo adventures, or guided and escorted tours.
Milan Travel Styles
Explore Milan with our diverse travel styles! Choose from luxurious tours that pamper you with comfort and elegance, or budget-friendly options that let you experience the beauty of Milan without breaking the bank. Whether you're indulging in fine dining or discovering hidden gems, there's a perfect adventure waiting for you.
Get a customized trip to Milan in Winter
Plan a multi-country or regional adventure across Milan in Winter, with help from a local expert.
Alessandra GalassiTravel Expert in Italy
Danilo CataniaTravel Expert in Italy
Enrico Maria MalacarneTravel Expert in Italy
Elena KyrimiTravel Expert in Greece & Italy
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