10 Best Milan Multiday Tours in October 2026

Get a customized trip to Milan in October 2026

Plan a multi-country or regional adventure across Milan in October 2026, 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
Simon H.Travel Expert in Belgium, France, Italy & Switzerland

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Accommodations

BudgetSimple stays with essential amenities. Typically guesthouses, hostels or hotels rated below 3 stars — clean, no-frills, and great for value-conscious travelers.
Mid-rangeComfortable and reliable 3-star stays. Expect private rooms, en-suite bathrooms, and solid amenities — a great balance between comfort and cost.
PremiumUpscale 4-5 star hotels and lodges. Enjoy high-end service, refined comfort, and premium locations — ideal for travelers seeking extra indulgence.

Super Sales

European Ring - October 2026

4.6

(14 reviews )

No booking fees

Best price guaranteed

The schedules were good only suggestion I would give I during summer when day temp can touch 35C have the day schedules a bit later, e.g in Rome the city walk tour starts at 3pm, rescheduled that for a bot later say 5.30pm, I suppose everyone in our group will agree considering the fact that there are women and children in the tour. This is good feedback and it can be considered for the future.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

15-99 yrs

Operated in

english

Destinations

Paris, Salzburg, Kitzbuhel, Vien

Paris, Salzburg, Kitzbuhel, Vienna, Prague, Frankfurt, Amsterdam, Lyon, Zurich, Milan, Rome

Duration23 days

From

USD 3,863

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Super Sales

Tutta Italia and Sicily with Aeolian Islands - October 2026

No booking fees

Best price guaranteed

Let the charm of Italy sweep you away on the 16-day Tutta Italia and Sicily with Aeolian Islands tour, crafted for those who appreciate a relaxed, insightful journey. Starting in Rome and ending in Palermo, this group tour weaves through Siena, Florence, and seven other captivating destinations. Senior travelers will appreciate the easy pace, comfortable accommodations, and seamless transport. The highlight is the opportunity to explore the picturesque Aeolian Islands—providing an idyllic contrast to Italy’s bustling cities and rich history.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Palermo, Venice, Milazzo

Rome, Palermo, Venice, Milazzo, Taormina, Siena, Florence, Genoa, Milan, Verona

Duration16 days

From

USD 3,236

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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 3,963

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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

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Super Sales

European Spotlight - October 2026

No booking fees

Best price guaranteed

Seeking a comprehensive European exploration? The 17-day 'European Spotlight' tour takes you from Lisbon to Rome, visiting Paris, Lyon, Zurich, and five more destinations along the way. With a focus on comfort and ease for mature travelers, this group city sightseeing journey provides hotels, transport, and meals. The unique benefit is the extensive itinerary, allowing you to experience a broad swath of Europe’s cultural and scenic highlights in a single trip.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Lisbon, Rome, Lyon, Zurich, Mila

Lisbon, Rome, Lyon, Zurich, Milan, Madrid, Barcelona, Paris

Duration17 days

From

USD 3,611

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Rome Revealed: A Classic City Break - October 2026

Trip customizable

Best price guaranteed

Discover the timeless charm of Rome with this 3-night city break, featuring 4-star accommodation and daily breakfast. Enjoy seamless private transfers to and from the airport or train station, and immerse yourself in the city’s rich history with guided tours of the Vatican Museums and the Sistine Chapel, as well as the Roman Forum, Palatine Hill, and Colosseum. With entrance tickets, professional guides, and headsets included, this package offers an unforgettable journey through the Eternal City

Explorer

Tour Type

Private Tour

Accommodation

Hotel

Age Range

12-99 yrs

Operated in

english

Destinations

Milan, Rome

Duration4 days

From

USD 794

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10% OFF TODAY

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

10% OFF TODAY

Duration9 days

From

USD 1,635

USD 1,472

Saving

USD 164

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Super Sales

Contrasts of Europe - October 2026

(2 reviews )

No booking fees

Best price guaranteed

The "Contrasts of Europe" tour invites you to traverse the continent from Lisbon to Amsterdam over 24 days, all at a comfortable, senior-friendly tempo. This guided city sightseeing tour includes everything you need for a worry-free experience: accommodations, transport, and meals. Ideal for those who appreciate the art of slow travel, this trip’s unique selling point is its extensive cross-European route—offering a vivid contrast of cultures, architecture, and landscapes from Portugal to Holland. Enjoy the company of fellow travelers and the reassurance of a group setting as you discover Europe’s many facets.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

15-99 yrs

Operated in

english

Destinations

Lisbon, Budapest, Milan, Rome, F

Lisbon, Budapest, Milan, Rome, Florence, Vienna, Madrid, Barcelona, Amsterdam, Prague, Zurich

Duration24 days

From

USD 3,759

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Super Sales

Italian Roundabout Complete End Venice - October 2026

No booking fees

Best price guaranteed

For seniors seeking a comfortable yet immersive Italian experience, the 18-day Italian Roundabout Complete End Venice tour is an excellent choice. Starting in Rome and concluding in the romantic city of Venice, this easy-paced sightseeing trip covers Genoa, Siena, Taormina, and ten other must-see locations. With all accommodations, transport, and meals expertly organized, you can relax as you soak up Italy’s art, history, and cuisine. The USP of this tour is its thoughtfully balanced itinerary, allowing guests to savor the country’s highlights at a gentle, enjoyable rhythm.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Venice, Siena, Florence, G

Rome, Venice, Siena, Florence, Genoa, Milan, Verona, Bari, Brindisi, Naples, Salerno, Taormina, Palermo

Duration19 days

From

USD 3,708

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15% OFF TODAY

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, La Spezia

15% OFF TODAY

Duration8 days

From

USD 4,325

USD 3,676

Saving

USD 649

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15% OFF TODAY

Colosseum to Como - 12 days - October 2026

No booking fees

Best price guaranteed

Discover the heart of Italy and beyond on this 12-day journey from Rome to Milan. Begin with sightseeing of the Colosseum and Roman Forum in the Eternal City before travelling through Assisi, Siena and the Renaissance treasures of Florence. Enjoy Bologna’s food culture, glide through Venice’s canals, and wander Shakespearean Verona with a stop for wine tasting in Franciacorta. Highlights also include a boat trip on Lake Garda, the elegance of Lake Como, and a spectacular ride on Switzerland’s Bernina Express. Round your tour off in stylish Milan, with guided touring and free time to explore your way.

Explorer

Tour Type

Group Tour

Accommodation

Hotel, Luxury Hotel, Resort

Age Range

18-80 yrs

Operated in

english

Destinations

Milan, Rome, Florence, Venice, Bergamo

15% OFF TODAY

Duration12 days

From

USD 5,705

USD 4,849

Saving

USD 856

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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 2,978

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Classic Italy & the Dolomites - October 2026

Trip customizable

Best price guaranteed

From the historic wonders of Rome, Florence, and Venice to the chic elegance of Milan, discover Italy’s rich culture, art, and cuisine. Travel by train and coach through Bologna, Verona, and Lake Garda, then board the scenic Bernina Express into the Swiss Alps. Explore the enchanting Dolomites, picturesque lakes, and hidden gems like Bolzano, Cortina, and Bassano del Grappa. With guided tours, local tastings, and unforgettable scenery, this immersive itinerary offers the perfect blend of Italy’s classics and natural treasures

Explorer

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

12-99 yrs

Operated in

english

Destinations

Milan, Rome, Florence, Dolomites

Milan, Rome, Florence, Dolomites, Venice, Bolzano, Merano

Duration13 days

From

USD 4,892

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Italy’s Grand Tour - October 2026

Trip customizable

Best price guaranteed

Discover world-famous landmarks, medieval towns, and stunning natural landscapes while indulging in Italy’s rich culinary traditions. Explore ancient ruins in Rome, the masterpieces in Florence, and romantic canals in Venice. Journey through the lakes of Como and Garda, ride the scenic Bernina Express through the Swiss Alps, and wander the cultural treasures of Milan, Bolzano, and Cortina d’Ampezzo. With guided tours, regional delicacies, and unforgettable scenic drives, this grand tour offers the very best of Italy—perfectly crafted for travelers seeking a once-in-a-lifetime Italian experience

Explorer

Tour Type

Group Tour

Accommodation

Hotel, Luxury Hotel, Resort

Age Range

12-99 yrs

Operated in

english

Destinations

Milan, Rome, Bolzano, Merano, Do

Milan, Rome, Bolzano, Merano, Dolomites, Florence, Venice, Bergamo

Duration17 days

From

USD 5,956

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All Milan Tours in October 2026

Page 4 of 67 Trips in Milan during October 2026 with 451 Reviews

Get a customized trip to Milan in October 2026

Page 4 of 67 Trips in Milan during October 2026 with 451 Reviews

European Ring - October 2026

Tutta Italia and Sicily with Aeolian Islands - October 2026

Classic Italy & the Northern Lakes - October 2026

Rome Florence Venice and Milan by Rail - October 2026

European Spotlight - October 2026

Rome Revealed: A Classic City Break - October 2026

Paris to Rome by Train - October 2026

Contrasts of Europe - October 2026

Italian Roundabout Complete End Venice - October 2026

Milan, Liguria & Venice - 8 days - October 2026

Colosseum to Como - 12 days - October 2026

Highlights of Northern Italy: Small Group Tour - October 2026

Classic Italy & the Dolomites - October 2026

Italy’s Grand Tour - October 2026

Europe

Asia

South America

Africa

North America

Oceania

Polar

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 October 2026

Page 4 of 67 Trips in Milan during October 2026 with 451 Reviews

Get a customized trip to Milan in October 2026

Page 4 of 67 Trips in Milan during October 2026 with 451 Reviews