10 Best Milan Multiday Tours in September 2026

Get a customized trip to Milan in September 2026

Plan a multi-country or regional adventure across Milan in September 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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Highlights of Northern Italy: Small Group Tour - September 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 2,999

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Northern Lakes, Milan & Cinque Terre with Bernina - September 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 3,920

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Classic Italy & the Italian Riviera - September 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 4,356

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Northern Lakes & the Dolomites with Bernina Expres - September 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 4,641

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Italy’s Lakes & Bernina Express: Small Group Tour - September 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 2,642

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Classic Italy & the Dolomites - September 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 4,927

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5% OFF TODAY

Simply Italy 35 to 45 - September 2026

No booking fees

Best price guaranteed

Welcome to 15 days of pure Italian travel immersion with your squad of awesome 35-45 year old travellers. 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 in the breezy winter 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!

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

18-35 yrs

Operated in

english

Destinations

Rome, Naples, Amalfi Coast, Flor

Rome, Naples, Amalfi Coast, Florence, Cinque Terre, Milan, Venice

5% OFF TODAY

Duration15 days

From

USD 3,031

USD 2,879

Saving

USD 152

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Paris to Rome by Train - September 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

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18% OFF TODAY

Super Sales

Milan City Break - September 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 357

USD 294

Saving

USD 63

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Super Sales

Europe by Rail Budapest to Milan - September 2026

(36 reviews )

No booking fees

Best price guaranteed

Wonderful trip, loved all the destinations! Our guide Sanne was incredible too and very knowledgable about the places we went to.

AdventureTrain tours

Tour Type

Group Tour

Accommodation

Hostel

Age Range

18-40 yrs

Operated in

english

Destinations

Budapest, Milan, Vienna, Bled, Venice

Duration11 days

From

USD 1,975

USD 1,916

Saving

USD 59

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Alpine Elegance: Small Group Tour to the Dolomites - September 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 3,492

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Signature Italy - September 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 5,355

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Italy’s Grand Tour - September 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 5,998

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Classic Italy & the Northern Lakes - September 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 3,991

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All Milan Tours in September 2026

Page 3 of 43 Trips in Milan during September 2026 with 558 Reviews

Get a customized trip to Milan in September 2026

Page 3 of 43 Trips in Milan during September 2026 with 558 Reviews

Highlights of Northern Italy: Small Group Tour - September 2026

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

Classic Italy & the Italian Riviera - September 2026

Northern Lakes & the Dolomites with Bernina Expres - September 2026

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

Classic Italy & the Dolomites - September 2026

Simply Italy 35 to 45 - September 2026

Paris to Rome by Train - September 2026

Milan City Break - September 2026

Europe by Rail Budapest to Milan - September 2026

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

Signature Italy - September 2026

Italy’s Grand Tour - September 2026

Classic Italy & the Northern Lakes - September 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 September 2026

Page 3 of 43 Trips in Milan during September 2026 with 558 Reviews

Get a customized trip to Milan in September 2026

Page 3 of 43 Trips in Milan during September 2026 with 558 Reviews