10 Best Milan Multiday Tours in October 2026

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Classic Italy & the Italian Riviera - October 2026

Trip customizable

Best price guaranteed

From the timeless beauty of Rome, Florence, and Venice to the coastal charm of Portofino and the colorful villages of Cinque Terre, discover Italy’s rich cultural heritage, breathtaking landscapes, and culinary delights. Travel in comfort by deluxe coach and high-speed train, enjoy guided visits to iconic sites, sample regional specialties, and ride the legendary Bernina Express through the Swiss Alps. This itinerary blends classic cities, coastal gems, and alpine wonder into one unforgettable Italian adventure

Explorer

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

12-99 yrs

Operated in

english

Destinations

Rome, Venice, Florence, Milan, L

Rome, Venice, Florence, Milan, Liguria, Cinque Terre

Duration11 days

From

USD 4,375

USD 4,244

Saving

USD 131

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Halloween Super Sales

Alpine Elegance: Small Group Tour to the Dolomites - October 2026

Trip customizable

Best price guaranteed

Experience the magic of Northern Italy and the scenic Alps on this 9-day small group tour that combines elegant cities and breathtaking Alpine landscapes. Begin in Milan with a guided city tour and ride the world-renowned Bernina Express through dramatic mountain passes. Discover the lakeside charm of Peschiera del Garda, explore medieval towns like Bolzano, Merano, and Vipiteno, and savor the natural wonders of the Dolomites, including Lake Braies and Tre Cime di Lavaredo. With curated local experiences, this journey is perfect for travelers seeking culture, nature, and unforgettable views

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel, Resort

Age Range

7-99 yrs

Operated in

english

Destinations

Milan, Bolzano, Merano, Cortina

Milan, Bolzano, Merano, Cortina, Dolomites

Duration9 days

From

USD 3,507

USD 3,402

Saving

USD 105

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Halloween Super Sales

Lake Maggiore, Como & Garda - 8 days - October 2026

No booking fees

Best price guaranteed

ITALY BY TRAIN: Discover the three most popular Italian Lakes on this 8-day tour, staying besides Lake Maggiore, Lake Como and Lake Garda. Travel by first-class train and enjoy free time at each lake. From Lake Maggiore, there's an optional scenic rail journey to lakeside Locarno in Switzerland via the Centovalli and in Milan there's the opportunity to enjoy a journey on the iconic Bernina Express to St Moritz. End your Italian adventure with two nights in Italy's fashion capital, Milan.

Explorer

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-80 yrs

Operated in

english

Destinations

Milan, Stresa, Lake Maggiore, Co

Milan, Stresa, Lake Maggiore, Como, Desenzano, Lake Garda

Duration8 days

From

USD 2,675

USD 2,595

Saving

USD 80

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Halloween Super Sales

Paris to Rome by Train - October 2026

(1 review )

No booking fees

Best price guaranteed

This was a great trip to explore each city. Personally, this felt a bit more independent type travel (exploring the city by yourself or if you made a friend with them) vs other Contikis (more time with the group). Hotels were great and fantastic locations (centrally located near metros and the main train station). Fantastic free time add ons as well.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-35 yrs

Operated in

english

Destinations

Paris, Rome, Lausanne, Milan, Venice

Duration9 days

From

USD 1,635

USD 1,586

Saving

USD 49

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18% OFF TODAY

Halloween Super Sales

Milan City Break - October 2026

Trip customizable

Best price guaranteed

Milan, the bustling metropolis of northern Italy, is renowned worldwide as a fashion and design capital, boasting historic fashion houses and cutting-edge contemporary designers. The city's architectural treasures include the magnificent Gothic cathedral, Duomo di Milano, and the grandiose opera house, Teatro alla Scala. Milan is also a hub of cultural richness, with world-class art galleries like the Pinacoteca di Brera and Leonardo da Vinci's iconic mural, "The Last Supper," housed in the Convent of Santa Maria delle Grazie.

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Milan

18% OFF TODAY

Duration4 days

From

USD 358

USD 295

Saving

USD 63

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Italian Lakes, Alps & Dolomites - 9 Days - October 2026

18% OFF TODAY

Halloween Super Sales

Italian Lakes, Alps & Dolomites - 9 days - October 2026

No booking fees

Best price guaranteed

Discover the beauty of northern Italy on this 9-day journey, starting and ending in Milan. Begin with time to explore the fashion capital before crossing into Switzerland for a spectacular ride on the Bernina Express. Back in Italy, enjoy a guided walking tour of Milan before heading to Lake Garda, Trento and the alpine charm of Bolzano. Explore medieval towns, sip local wines and take in the breathtaking lakes of the Dolomites from a base in Cortina d’Ampezzo, then head back to Milan via Bassano del Grappa, with a tasting of the local tipple.

Explorer

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

18-80 yrs

Operated in

english

Destinations

Milan, Bolzano, Cortina d'Ampezzo

18% OFF TODAY

Duration9 days

From

USD 3,475

USD 2,865

Saving

USD 610

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Halloween Super Sales

Rome Florence Venice and Milan by Rail - October 2026

Trip customizable

Best price guaranteed

This tour will take you on a memorable train ride across the major touristic cities of Italy. You’ll begin by exploring Rome, with stunning feats of civilization, modern and age-old alike. Colosseum, Navona Square, Pantheon, Spain Square, and Trevi Fountain are a few places that you can visit. The next place where you’ll take a train would be Florence. History, art, countryside, and delicious food are the gist of what this capital city of Tuscany has in store for you. Accademia and Uffizi Galleries are a must-visit. After Florence, The City of Water, Venice, awaits your arrival. Though the journey to Venice via rail is gorgeous, the city itself has its charm. Riding into a gondola through the Grand Canal and being mesmerized by the city’s beauty should be on your list. In addition, take a walking tour covering St Mark’s Square, Doge's Palace, Bell Tower, etc. Finally, we are at the last city of this train tour—Milan. An epitome of great fashion and design, Milan is a heart stealer. Apart from the latest cultural trends, you can even get a slice of history by visiting the Milan Cathedral. Also, ensure not to miss Leonardo Da Vinci’s stupefying Cenacolo, the Last Supper, which is one of the most famous artworks in the world. This train journey is one of the most popular Italy travel packages, offering a comprehensive tour of Italy's iconic cities.

Explorer

Tour Type

Independent Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

English

Destinations

Milan, Rome, Florence, Venice

Duration9 days

From

USD 1,102

USD 1,069

Saving

USD 33

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Milan, Liguria & Venice - 8 Days - October 2026

18% OFF TODAY

Halloween Super Sales

Milan, Liguria & Venice - 8 days - October 2026

No booking fees

Best price guaranteed

Discover northern Italy and the Swiss Alps on this 8-day group tour from Milan to Venice via Liguria. Start with guided sightseeing and free time to explore Milan’s fashion streets and landmarks before crossing into Switzerland for the Bernina Express, one of the world’s most scenic train rides. Journey on to the Ligurian coast to visit Portofino and the colourful Cinque Terre villages, then travel inland for a taste of Ferrari heritage in Maranello and traditional balsamic vinegar in Modena. End your trip in magical Venice, with its canals, piazzas and iconic sights.

Explorer

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

18-80 yrs

Operated in

english

Destinations

Milan, Venice

18% OFF TODAY

Duration8 days

From

USD 4,365

USD 3,599

Saving

USD 766

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Halloween Super Sales

Highlights of Northern Italy: Small Group Tour - October 2026

Trip customizable

Best price guaranteed

Embark on an unforgettable 8-day small group journey through Northern Italy, from Milan to romantic Venice, with breathtaking experiences along the way. Ride the world-famous Bernina Express through the Swiss Alps, wander the colorful coastal villages of the Cinque Terre, and explore the elegance of Portofino. Indulge in local food and wine tastings in Liguria and Modena, and dive into Italian automotive excellence at the Ferrari Museum. With hand-picked hotels, expert local guides, and unique culinary moments, this tour blends culture, scenery, and flavour for the perfect Northern Italian trip

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel, Resort

Age Range

7-99 yrs

Operated in

english

Destinations

Milan, Venice, Liguria, Cinque Terre

Duration8 days

From

USD 3,012

USD 2,922

Saving

USD 90

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Halloween Super Sales

Signature Italy - October 2026

Trip customizable

Best price guaranteed

Experience the best of Italy on this unforgettable 15-day journey. Walk in the footsteps of emperors at the Colosseum, explore Renaissance treasures in Florence, and glide along Venice’s canals. Savor Tuscan flavors, sip Franciacorta wines, and enjoy authentic culinary experiences from Bologna to Modena. Cruise the pristine waters of Lake Garda and Lake Como, ride the legendary Bernina Express through the Swiss Alps, and wander the colorful villages of Cinque Terre and Portofino. With expert guides, handpicked hotels, this is Italy at its most enchanting

Explorer

Tour Type

Group Tour

Accommodation

Hotel, Luxury Hotel, Resort

Age Range

12-99 yrs

Operated in

english

Destinations

Rome, Venice, Milan, La Spezia

Rome, Venice, Milan, La Spezia, Florence, Bergamo

Duration15 days

From

USD 5,379

USD 5,218

Saving

USD 161

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Halloween Super Sales

Northern Lakes, Milan & Cinque Terre with Bernina - October 2026

Trip customizable

Best price guaranteed

Begin in enchanting Venice, soaking in its canals and signature Venetian flavors, then journey through the romantic streets of Verona and the rolling vineyards of Franciacorta. Take in the beauty of Lake Garda, Lake Como, and Bellagio, where charming lakeside villages meet breathtaking Alpine views. From Milan, board the legendary Bernina Express for a scenic rail journey through the Swiss Alps. Continue to the Ligurian coast to explore glamorous Portofino and the iconic Cinque Terre, before indulging in Modena’s rich motor and culinary traditions

Explorer

Tour Type

Group Tour

Accommodation

Hotel, Luxury Hotel, Resort

Age Range

12-99 yrs

Operated in

english

Destinations

Venice, Bergamo, Milan, La Spezia

Duration11 days

From

USD 3,937

USD 3,819

Saving

USD 118

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Halloween Super Sales

Northern Lakes & the Dolomites with Bernina Expres - October 2026

Trip customizable

Best price guaranteed

Begin in Venice with its timeless charm, then explore historic Verona, the vineyards of Franciacorta, and the scenic beauty of Lake Garda and Lake Como. Ride the famous Bernina Express through the Swiss Alps, uncover Milan’s cultural gems, and journey through the elegant towns of Bolzano, Merano, and Cortina d’Ampezzo. With guided tours, wine tastings, scenic boat rides, and unforgettable landscapes, this immersive itinerary blends Italy’s refined heritage with natural beauty at every turn

Explorer

Tour Type

Group Tour

Accommodation

Hotel, Luxury Hotel, Resort

Age Range

12-99 yrs

Operated in

english

Destinations

Milan, Venice, Cortina, Dolomite

Milan, Venice, Cortina, Dolomites, Bergamo, Bolzano, Merano

Duration13 days

From

USD 4,662

USD 4,522

Saving

USD 140

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Halloween Super Sales

Italy’s Lakes & Bernina Express: Small Group Tour - October 2026

Trip customizable

Best price guaranteed

Experience the best of Northern Italy and the Swiss Alps on this unforgettable 8-day small group tour. Explore the romantic canals of Venice, sip wine in Franciacorta, cruise across Lakes Garda and Como, and ride the iconic Bernina Express through breathtaking alpine landscapes. With guided city tours, scenic boat rides, and wine tastings, this journey blends culture, charm, and natural beauty—perfect for travelers seeking a relaxed yet enriching Italian escape

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel, Luxury Hotel, Resort

Age Range

7-99 yrs

Operated in

english

Destinations

Milan, Venice, Bergamo

Duration8 days

From

USD 2,653

USD 2,574

Saving

USD 80

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Halloween Super Sales

Classic Italy & the Northern Lakes - October 2026

Trip customizable

Best price guaranteed

Begin in the Eternal City with ancient wonders like the Colosseum before traveling through the hill towns of Assisi and Siena to Renaissance Florence. Savor the flavors of Bologna and glide through the romantic canals of Venice. Discover Shakespearean Verona, sip wine in Franciacorta, and admire the scenic beauty of Lake Garda, Como, and Bellagio. Conclude in Milan with a thrilling ride on the Bernina Express through the Swiss Alps and a guided tour of the city’s iconic landmarks. From medieval towns to alpine peaks, this tour is a perfect blend of Italy’s timeless charm and natural beauty

Explorer

Tour Type

Group Tour

Accommodation

Hotel, Luxury Hotel, Resort

Age Range

12-99 yrs

Operated in

english

Destinations

Milan, Rome, Florence, Venice, Bergamo

Duration12 days

From

USD 4,009

USD 3,889

Saving

USD 120

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All Milan Tours in October 2026

Page 3 of 50 Trips in Milan during October 2026 with 373 Reviews

Get a customized trip to Milan in October 2026

Page 3 of 50 Trips in Milan during October 2026 with 373 Reviews

Classic Italy & the Italian Riviera - October 2026

Alpine Elegance: Small Group Tour to the Dolomites - October 2026

Lake Maggiore, Como & Garda - 8 days - October 2026

Paris to Rome by Train - October 2026

Milan City Break - October 2026

Italian Lakes, Alps & Dolomites - 9 days - October 2026

Rome Florence Venice and Milan by Rail - October 2026

Milan, Liguria & Venice - 8 days - October 2026

Highlights of Northern Italy: Small Group Tour - October 2026

Signature Italy - October 2026

Northern Lakes, Milan & Cinque Terre with Bernina - October 2026

Northern Lakes & the Dolomites with Bernina Expres - October 2026

Italy’s Lakes & Bernina Express: Small Group Tour - October 2026

Classic Italy & the Northern Lakes - October 2026

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Food, wine, events and nightlife

Adventure and sport

Wildlife, landscapes and nature

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Sightseeing, attractions, culture and history

Air tours, road trips and transfers

Beach, romance, getaways and relaxation

Special interests and hobbies

All Milan Tours in October 2026

Page 3 of 50 Trips in Milan during October 2026 with 373 Reviews

Get a customized trip to Milan in October 2026

Page 3 of 50 Trips in Milan during October 2026 with 373 Reviews