10 Best Milan Multiday Tours in Winter

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Italian Intermezzo - Winter tours

4.6

(51 reviews )

No booking fees

Best price guaranteed

This tour is the BEST way to see all the infamous spots in Italy, plus local hidden gems, at a reasonable cost and if you are short on time (we had a school break time limitation). It covered everything! We budgeted for the add-ons, especially those with meals, but you could choose to have more free time if you wanted. The food was extraordinary, the bus was roomy and immaculately clean, our driver Antonello was superb, and our Travel Director Anneleis was amazing! She was so talented at integrating the tour highlights, guests, keeping it fun even in the rainy weather, knowledgeable, and able to troubleshoot anything to ensure we had the best experience of a lifetime!! I would love to go back and explore Southern Italy next. The hotels were elegant (only one was just "OK" only because it was in need of some renovations) and the service with our luggage, tipping, etc. was seamless. I highly recommend the Italian Intermezzo tour and Insight Vacations. Favoloso!

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Milan, Rome, Venice, Florence

21% OFF TODAY

Duration8 days

From

USD 3,395

USD 2,667

Saving

USD 728

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Jewels of Italy and Milan by Rail - Winter tours

(1 review )

Trip customizable

Best price guaranteed

I’ve always loved Italy, but doing it by rail added a special touch. Over eight days, we hit Rome, Florence, Venice, and wrapped up in Milan, all by high-speed train. The pace worked perfectly for me (I’m 58), with fresh city arrivals each morning and comfortable hotels each night The highlights: a hop-on hop-off loop in Rome hit the Colosseum, Pantheon, Trevi Fountain , an optional wine tasting tour that I booked in Florence and Venice’s gondola ride. Everything flowed perfectly well..no dragging suitcases or missed trains. For travelers in our age bracket, this tour blends comfort, culture, and hassle-free travel. If you want Italy’s treasures without the planning headache, this rail tour delivers in a big way.

City sightseeingTrain tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

english

Destinations

Milan, Rome, Florence, Venice

Duration8 days

From

USD 1,417

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Amazing Italy - Winter tours

(3 reviews )

Trip customizable

Best price guaranteed

Absolutely incredible! Italy’s history, food, and charm blew us away. The small group setting was perfect, and everything was tailored for Canadian travelers. Highly recommend!

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

english

Destinations

Rome, Florence, Verona, Sorrento

Rome, Florence, Verona, Sorrento, Venice, Perugia, Naples, Salerno, Siena, Genoa, Milan

Duration15 days

From

USD 2,624

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Italian Scene - Winter tours

4.6

(49 reviews )

No booking fees

Best price guaranteed

The scenery was beautiful. Next time I'd slow it down a bit though and enjoy each city for a few days.

Countryside and village visits

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Bay Of Naples, Assisi, Ven

Rome, Bay Of Naples, Assisi, Venice, Milan, Florence

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Duration10 days

From

USD 1,950

USD 1,853

Saving

USD 97

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Reflections of Italy - Winter tours

No booking fees

Best price guaranteed

Embark on a captivating journey that takes you from the piazzas of Rome to the canals of Venice. Discover the rolling hills of the scenic Tuscan and Umbrian countryside. Explore medieval hill towns and visit Assisi, the birthplace of St. Francis. Spend time at a historic winery in the heart of the Chianti region and enjoy a chef-led cooking class with lunch. Discover the masterpieces of the Renaissance in Florence. See glass transformed into exquisite art on Murano Island. Linger in iconic Venice for 2 nights. Journey to the shores of glamorous Lake Como. Encounter a land rich in history, culture, art, and romance.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Milan, Rome

Duration10 days

From

USD 2,949

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Absolute Italy by Rail - Winter tours

Trip customizable

Best price guaranteed

Visit Italy’s major highlights as you travel by rail on one of our exclusive Italy tours and packages. Your tour starts in Italy’s capital: Rome where you will get to see the incredible monumental heritage of the city and its ancient Roman architecture. Embrace the remarkable topography of the country while on a high-speed rail. In Florence you will get to see intact medieval walls at Monteriggioni and famous medieval towers at walled town San Gimignano. In Cinque Terre, you will have the opportunity to discover the area freely, as you will have a pass that give you access all over the village of Cinque Terre. Next stop would be Milan the city of Fashion and Arts, where you will discover the Last Supper of Leonardo Da Vinci, the famous Gothic Cathedral, La Scala Opera House or the other hidden treasures of Milan. From here you will be visiting Venice which would be your last stop on this wonderful trip. You will get to see Piazza San Marco with the Basilica and the Clock Tower, the Rialto Bridge, Campo Santa Maria Formosa and the Grand Canal or escape to the more tranquil side streets and small canals that criss–cross the city.

Train tours

Tour Type

Independent Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

English

Destinations

Rome, Florence, Venice, La Spezi

Rome, Florence, Venice, La Spezia, Milan

Duration12 days

From

USD 2,467

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Italian Treasures - Winter tours

Trip customizable

Best price guaranteed

Get ready to see some of the most famous landmarks, fascinating attractions, and architectural sites in Southern Europe with this 12-day tour of Italy! Your journey will begin in Rome, home to the world-famous Colosseum and the Trevi Fountain. Take a trip to Vatican City, where you will visit St. Peter’s Basilica, the largest church in the world. From there, you will travel to Florence, the Birthplace of the Renaissance. Head over to the hilltop Piazzale Michelangelo, situated by the banks of the River Arno, to uncover the best views of Florence in the city. Make your way west to see the Leaning Tower of Pisa and drive through Cinque Terre, a World Heritage Site consisting of five Italian villages, known for its scenic trails stretching along the coast of the Italian Riviera. Take the train to Levanto to explore the Genoa Old Port and visit Santa Margherita Ligure. Lay back in the Riviera Region in Portofino before you travel to Milan, the fashion capital of Italy. From there, you will explore the Italian Lakes Region with breathtaking trips to Lake Orta, Lake Maggiore, and the Borromean Islands. Your next destination will be Verona, the home of Romeo and Juliet. Head on a boat ride to St. Mark’s Square in Venice, the City of Canals. Stop in Padova before you travel to the Adriatic coast to see San Marino, an independent country sitting atop a fortified mountain. Pass by Gubbio, home to the Palace of Consuls, and travel to Perugia, surrounded by the valleys and mountains of Umbria. Explore Assisi and see the Basilica of St. Francis before you make your way back to Rome, where your tour of Italy will come to an end. This well-rounded itinerary is perfect for those seeking immersive and unforgettable Italy vacations.

Art and architectureCulture

Tour Type

Group Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

english

Destinations

Rome, Florence, Verona, Umbria &

Rome, Florence, Verona, Umbria & Marche, Perugia, Genoa, Milan, Venice

Duration11 days

From

USD 1,837

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Essential Portugal, Spain, Switzerland and Italy - Winter tours

(4 reviews )

Trip customizable

Best price guaranteed

Four amazing countries in one trip! Each place had its own unique charm, and the itinerary was perfectly balanced. Switzerland’s Alps and Italy’s gelato were highlights!

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

8-99 yrs

Operated in

english

Destinations

Lisbon, Rome, Zurich, Mont Blanc

Lisbon, Rome, Zurich, Mont Blanc, Milan, Madrid, Barcelona, Girona, Leysin

Duration13 days

From

USD 2,309

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Treasures of Paris, Switzerland, Italy and Vienna - Winter tours

Trip customizable

Best price guaranteed

Get ready to see some of the most fascinating cities and amazing landmarks of Europe with this 18-day tour! Start your journey sightseeing Paris, with a Cruise on the River Seine cruise and great views from the Eiffel Tower. Continue to travel to the center of France and explore the region of Bourgogne and Beaune, an area known for its wines. Admire views of castles and vineyards on the way to the Swiss Alps. Experience the rolling hills and majestic mountains of Switzerland. Tour Lake Geneva and enjoy the sights in the Lucern area. Crossover to Italy, a country rich in natural and artistic treasures. Explore its most famous cities: Rome, Milan, Florence, and Venice. While in Venice, admire some of the palazzos and maze of streets and take the opportunity to watch glassblowers create their works as they have done for centuries. Journey through spectacular mountain scenery and picturesque cities in Austria. Marvel the charming Alpine city of Innsbruck. Continue to Salzburg featured in the "Sound of Music", then to Vienna, once the center of the mighty Habsburg Empire and enjoy time cruising along the legendary Danube River. Finally end your tour in vibrant, cosmopolitan Budapest.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

8-99 yrs

Operated in

english

Destinations

Budapest, Paris, Zurich, Innsbru

Budapest, Paris, Zurich, Innsbruck, Rome, Florence, Venice, Kitzbuhel, Vienna, Lyon, Milan

Duration17 days

From

USD 3,097

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Essential Spain, Switzerland, Italy and Austria - Winter tours

Trip customizable

Best price guaranteed

About This Trip On this journey, you will discover some of the most famous destinations in Spain, Switzerland, Italy, and Austria. Start your journey in Barcelona, where you will go on a guided tour to the Monastery of Poblet, located in northeastern Spain, one of the best-preserved medieval monasteries in the world. In Barcelona, tour the city and discover the iconic Ras Ramblas Street. Your tour continues with driving in the region of Provence to arrive in the charming town of Chamberry. Continue to Switzerland and enjoy beautiful lakes and mountains with snow-capped peaks on your way to Zurich. Your journey continues in Rome, the ancient Capital of Italy, and get to know about its history on a panoramic tour and in the Trastevere area. You will also visit St. Peter’s Basilica in the heart of Vatican City and the impressive Roman Coliseum. Moving to Venice, you will take the boat, cross the Grand Canal to the Island of Venice, and visit the marvelous St. Mark´s Square and the Murano Glass Factory. Then travel along a scenic road between the mountains on your way to Kitzbuhel in Austria and take a cable car ride up to the high mountains surrounding the city with fantastic scenery. Later, you will explore the beautiful Traunsee Lake in Traunkirchen and see four castles. Your journey ends in Vienna with majestic avenues, its palaces, and its vibrant city center. Here you will visit the Schonbrunn Palace and enjoy its beautiful gardens.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

8-99 yrs

Operated in

english

Destinations

Vienna, Barcelona, Zurich, Innsb

Vienna, Barcelona, Zurich, Innsbruck, Venice, Kitzbuhel, Girona, Mont Blanc, Gstaad, Milan, Rome, Florence

Duration14 days

From

USD 2,414

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Rome Florence Venice Milan and Lake Como by Rail - Winter tours

(1 review )

Trip customizable

Best price guaranteed

This train tour across Italy allows you to explore some of the nation’s most prominent landmarks. It starts with Rome which is the foundation of Christian culture and Western civilization. When here, you can visit the Roman Colosseum, Navona Square, Trevi Fountain, St Peter's Basilica and the Vatican Museum. The next stop of this journey is Florence, the capital city of Tuscany. Known for Michelangelo’s David sculpture and taking you through chapters of the renaissance period one by one, Florence is a paradise for people loving art and history. Up next is the City of Canals, Venice. Believed to be of the most romantic cities in the world, Venice also boasts of Doge’s Palace and San Marco Square. The fourth destination of this tour is Milan, Italy’s fashion capital. Apart from being captivated by the stylish Milan streets, you can also explore the Duomo, the Castello Sforzesco, and the famous Navigli canals. Fifth in the line is the place of dreams, Lake Como. Renowned for fabulous lakeside resorts, fine dining restaurants, and alluring beauty, this place will take your breath away! Post this, you will travel back to Milan, coming to the end of one of our Scenic tours of Italy.

Train tours

Tour Type

Independent Tour

Accommodation

Hotel, Resort

Age Range

8-99 yrs

Operated in

English

Destinations

Rome, Lake Como, Milan, Florence

Rome, Lake Como, Milan, Florence, Venice

Duration11 days

From

USD 1,312

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From Prague To Venice Through The Majestic Alps - Winter tours

Trip customizable

Best price guaranteed

This trip will give you the pleasure of exploring some of the most amazing destinations Europe in the Czech Republic, Germany, Austria, Switzerland and Italy. Start your journey from Prague where you get to explore the city on a guided tour and enjoy a boat tour on the Vltava River. Then reach Munich and visit the futuristic BMW Welt which has fascinating architecture for multi-use exhibitions of BMW cars. Ahead in your journey to Austria arrive in Innsbruck and visit the Swarovski Museum, the renowned home of crystals. Then cross the border to Switzerland and enjoy an evening in the historic center next to the lake in Zurich. Next, take in the fantastic scenery while you ride up in a cable car in Grindelwald and explore the beautiful Lucern. later continued to Burglen and visited the chapel of the XVI century before reaching Milan in Italy. Next, you will discover the famous city of Pisa and take a little tourist train to the beautiful art complexes of Piazza Dei Miracoli and the well-known Leaning Tower. On your next stop you will reach the Italian Capital of Rome where you will visit St. Peter’s Basilica and the notorious Roman Coliseum among other highlights. Your adventure will continue with a walking tour of magnificent Florence through the historic center, taking in places such as the Ponte Vecchio, the Duomo, and Plaza della Signoria. Your journey will end in Romantic Venice, where you will discover the marvelous St. Mark´s Square and the world-famous Murano Glass Factory.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

english

Destinations

Venice, Prague, Zurich, Innsbruc

Venice, Prague, Zurich, Innsbruck, Milan, Rome, Florence

Duration11 days

From

USD 2,099

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A European Journey from Madrid to Prague - Winter tours

Trip customizable

Best price guaranteed

ABOUT THIS TRIP This incredible journey takes you to the highlights of the most iconic and important sights in Europe. Your journey begins in the capital of Spain, Madrid, where you will enjoy a comprehensive tour through the center, including Paseo del Prado, Cibeles, Neptuno, the Gate of Alcalá, Plaza de Colón, and Plaza Mayor. On the way to Barcelona, you will go on a guided tour to the Monastery of Poblet, located in northeastern Spain, one of the best-preserved medieval monasteries in the world. In Barcelona, tour the city and discover the iconic Ras Ramblas Street. Your tour continues with driving in the region of Provence to arrive in the charming town of Chamberry. Continue to Switzerland and enjoy beautiful lakes and mountains with snowcapped peaks on your way to Zurich. Your journey continues in Rome, the ancient Capital of Italy, and get to know about its history on a panoramic tour and in the Trastevere area. You will also visit St. Peter’s Basilica in the heart of Vatican City and the impressive Roman Coliseum. Moving to Venice, you will take the boat, cross the Grand Canal to the Island of Venice, and visit the marvelous St. Mark´s Square and the Murano Glass Factory. Then travel along a very scenic road between the mountains on your way to Kitzbuhel in Austria and take a cable car ride up to the high mountains that surround the city with fantastic scenery. Later, you will explore the beautiful Traunsee Lake in Traunkirchen and see four castles. The next stop is Vienna, with its majestic avenues, palaces, and vibrant city center. Here, you will visit the Schonbrunn Palace and enjoy its beautiful gardens. Next, you will continue to Hungary and discover its spectacular capital, Budapest on a Scenic city tour followed by a boat tour along the river Danube. Your journey will end in Prague, where your local expert will provide an informative city tour, and you will discover monuments, including Prague Castle dominates the city, before you take a boat tour on the Vltava River.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

8-99 yrs

Operated in

english

Destinations

Madrid, Prague, Zurich, Innsbruc

Madrid, Prague, Zurich, Innsbruck, Rome, Florence, Venice, Salzburg, Vienna, Budapest, Barcelona, Girona, Chambery, Leysin , Milan

Duration19 days

From

USD 3,097

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Italy Winter Snow and Alps - Winter tours

Trip customizable

Best price guaranteed

Get ready for a one-of-a-kind winter journey through Italy’s snow-covered Dolomites with Taste and Slow Italy’s “Winter Alps and Dolomites” tour. This seven-day adventure combines the serene beauty of Northern Italy with cultural heritage, outdoor fun, and festive holiday charm. Centered around Val Badia and Bolzano, this itinerary promises breathtaking landscapes, charming towns, and authentic winter experiences. Start your journey in Val Badia, staying at a cozy hotel in an enchanting valley surrounded by snow-capped peaks. Relax in the spa and savor local flavors before setting out on a guided snowshoe tour to the iconic Five Towers of Cortina d’Ampezzo, where you’ll enjoy panoramic mountain views and traditional refreshments. For ski lovers, Val Badia offers both cross-country and downhill options, with private lessons available for all levels. History enthusiasts will also appreciate the snowshoe tour to the Andraz Castle, a medieval fortress that brings the past to life against a stunning winter landscape. In Bolzano, embrace the holiday spirit with visits to charming Christmas markets. Wander through stalls offering artisanal gifts, mulled wine, and Apfelstrudel, and visit a Termeno winery to taste local wines like Gewürztraminer. Here, learn about the unique alpine terroir that gives these wines their distinct character. Conclude your tour with optional visits to Castel Roncolo, known for medieval frescoes, or take a scenic cable car to the Renon Plateau for stunning alpine views. This tour is perfect for those seeking both relaxation and adventure, blending Italy’s alpine charm, traditional hospitality, and majestic winter landscapes. Join us for an unforgettable winter escape that celebrates the best of Italy’s winter magic.

Culture shows and excursions

Tour Type

Private Tour

Age Range

1-90 yrs

Operated in

english

Destinations

Northern Italy, Dolomites, Bolza

Northern Italy, Dolomites, Bolzano, Milan

Duration7 days

From

USD 3,548

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All Milan Tours in Winter

17 Trips in Milan with 109 Reviews

Italian Intermezzo - Winter tours

Jewels of Italy and Milan by Rail - Winter tours

Amazing Italy - Winter tours

Italian Scene - Winter tours

Reflections of Italy - Winter tours

Absolute Italy by Rail - Winter tours

Italian Treasures - Winter tours

Essential Portugal, Spain, Switzerland and Italy - Winter tours

Treasures of Paris, Switzerland, Italy and Vienna - Winter tours

Essential Spain, Switzerland, Italy and Austria - Winter tours

Rome Florence Venice Milan and Lake Como by Rail - Winter tours

From Prague To Venice Through The Majestic Alps - Winter tours

A European Journey from Madrid to Prague - Winter tours

Italy Winter Snow and Alps - Winter tours

17 Trips in Milan with 109 Reviews

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Food, wine, events and nightlife

Adventure and sport

Wildlife, landscapes and nature

Boat tours, water sports and marine wildlife

Sightseeing, attractions, culture and history

Air tours, road trips and transfers

Beach, romance, getaways and relaxation

Special interests and hobbies

All Milan Tours in Winter

17 Trips in Milan with 109 Reviews

17 Trips in Milan with 109 Reviews