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

Start planning your Trip

Recommended by

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.

Halloween Super Sales

Central & Western Europe: Classic Cities - September 2026

No booking fees

Best price guaranteed

Find me... munching on strudel in a chandelier-lit Viennese café, chasing gelato through Florence’s cobbled streets, getting lost in Prague’s fairytale lanes and lazing by the river in laid-back Ljubljana.

Explorer

Tour Type

Small Group Tour

Accommodation

Camping, Hostel, Sleeper Train

Age Range

18-39 yrs

Operated in

english

Destinations

Amsterdam, Ljubljana, Venice, Ro

Amsterdam, Ljubljana, Venice, Rome, Florence, Milan, Swiss Alps, Berlin, Paris, Prague, Vienna

Duration25 days

From

USD 4,869

USD 4,723

Saving

USD 146

View Tour

Venice To Milan - 13 Days - September 2026

18% OFF TODAY

Halloween Super Sales

Venice to Milan - 13 days - September 2026

No booking fees

Best price guaranteed

Discover the best of northern Italy on this 13-day journey from Venice to Milan, weaving together iconic cities, shimmering lakes and spectacular Alpine scenery. Glide along Venice’s canals, sip spritz with cicchetti, and wander the romantic streets of Verona. Cruise Lake Garda and Lake Como, ride the world-famous Bernina Express through the Swiss Alps, and explore chic Milan. In Trentino-Alto Adige, uncover wine towns, Dolomite lakes and charming villages like Bolzano and Cortina. With guided tours, tastings and scenic drives, this trip blends culture, landscapes and food for a truly memorable Italian adventure.

Explorer

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

18-80 yrs

Operated in

english

Destinations

Milan, Venice, Cortina d'Ampezzo

Milan, Venice, Cortina d'Ampezzo, Bergamo, Bolzano

18% OFF TODAY

Duration13 days

From

USD 6,695

USD 5,520

Saving

USD 1,175

View Tour

Venice To Liguria Loop - 11 Days - September 2026

18% OFF TODAY

Halloween Super Sales

Venice to Liguria Loop - 11 days - September 2026

No booking fees

Best price guaranteed

Explore the best of northern Italy on this 11-day journey, starting and ending in Venice. Begin with a guided tour of Venice’s iconic sights before heading to romantic Verona and the wine country of Franciacorta. Cruise across Lake Garda and Lake Como, stopping in elegant Bellagio, then enjoy the spectacular Bernina Express through the Swiss Alps. Discover Milan’s grand landmarks before travelling to the Ligurian coast for Portofino and the colourful Cinque Terre. Along the way, enjoy tastings of local wines and delicacies, visit the Ferrari Museum in Maranello, and experience Modena’s famous balsamic vinegar tradition before returning to Venice.

Explorer

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

18-80 yrs

Operated in

english

Destinations

Venice, La Spezia, Bergamo, Milan

18% OFF TODAY

Duration11 days

From

USD 5,695

USD 4,696

Saving

USD 999

View Tour

Scenic Italy & Switzerland - 13 Days - September 2026

18% OFF TODAY

Halloween Super Sales

Scenic Italy & Switzerland - 13 days - September 2026

No booking fees

Best price guaranteed

Experience scenic Italy and Switzerland on this 13-day tour from Milan, blending lakeside beauty, historic cities, and dramatic alpine landscapes. Discover Lake Garda and fair Verona before immersing in the charm of Venice. Travel through the Dolomites for soaring peaks, alpine lakes, and sweeping passes, then continue to Trento. Cruise across Lake Como, explore elegant Stresa, and visit the UNESCO-listed Sacro Monte of Ghiffa. Cross the Simplon Pass to Zermatt for unforgettable views of the Matterhorn, then explore Lausanne, Gruyères and Gstaad. End the adventure with Lauterbrunnen’s waterfalls, Interlaken’s Mountain scenery, Entlebuch’s pastures and Bellinzona’s medieval castles before returning to Milan.

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel, Resort, Villa

Age Range

18-80 yrs

Operated in

english

Destinations

Milan, Venice, Lausanne, Interla

Milan, Venice, Lausanne, Interlaken, Cortina d'Ampezzo, Trento, Locarno

18% OFF TODAY

Duration13 days

From

USD 7,835

USD 6,460

Saving

USD 1,375

View Tour

Rome To Milan Encompassed - 17 Days - September 2026

18% OFF TODAY

Halloween Super Sales

Rome to Milan Encompassed - 17 days - September 2026

No booking fees

Best price guaranteed

Journey through Italy and beyond on this 17-day tour, starting in Rome and ending in Milan. Begin with ancient wonders like the Colosseum and Roman Forum, before travelling through Assisi, Siena, and Florence, the cradle of the Renaissance. Taste Bologna’s rich gastronomy, glide through Venice’s canals with a spritz in hand, and wander Verona’s romantic streets. Cruise Lake Garda and Lake Como, sip sparkling wines in Franciacorta, and ride the scenic Bernina Express through the Swiss Alps. From Bolzano and Cortina’s Alpine charm to Bassano del Grappa’s traditions, before ending in Milan

Explorer

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

18-80 yrs

Operated in

english

Destinations

Milan, Rome, Bolzano, Cortina d'

Milan, Rome, Bolzano, Cortina d'Ampezzo, Florence, Venice, Bergamo

18% OFF TODAY

Duration17 days

From

USD 7,715

USD 6,361

Saving

USD 1,354

View Tour

Rome To Florence, Alps & Dolomites - 13 Days - September 2026

18% OFF TODAY

Halloween Super Sales

Rome to Florence, Alps & Dolomites - 13 days - September 2026

No booking fees

Best price guaranteed

Discover Italy and Switzerland on this 13-day journey from Rome to Milan, uncovering art, history and stunning landscapes along the way. Wander medieval Assisi and Siena before delving into Florence’s Renaissance treasures. Explore Bologna’s lively piazzas and Venice’s canals, then continue to chic Milan. Ride the Bernina Express through the Swiss Alps, take in Lake Garda and the wine routes of Trento and Kaltern, and enjoy the Alpine charm of Bolzano, Merano and Vipiteno. Marvel at the lakes and peaks of the Dolomites from Cortina d’Ampezzo, before rounding off with a taste of Bassano del Grappa’s heritage and culture.

Explorer

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

18-80 yrs

Operated in

english

Destinations

Milan, Rome, Florence, Cortina d

Milan, Rome, Florence, Cortina d'Ampezzo, Venice, Bolzano

18% OFF TODAY

Duration13 days

From

USD 7,095

USD 5,850

Saving

USD 1,245

View Tour

Milan To Venice & The Dolomites - 6 Days - September 2026

18% OFF TODAY

Halloween Super Sales

Milan to Venice & the Dolomites - 6 days - September 2026

No booking fees

Best price guaranteed

Discover northern Italy on a 6-day adventure from Milan to the Dolomites and back. The journey begins at sparkling Lake Garda before continuing to Shakespeare’s Verona and enchanting Venice, explored on a guided tour of its canals and piazzas. Rolling prosecco hills in Valdobbiadene lead the way into the Dolomites, where alpine lakes, soaring peaks and panoramic cable car rides showcase the region’s natural beauty. Historic Trento and Bergamo’s hilltop old town provide a cultural finale before returning to Milan.

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel, Resort

Age Range

18-80 yrs

Operated in

english

Destinations

Milan, Venice, Cortina D’Ampezzo

Milan, Venice, Cortina D’Ampezzo, Trento

18% OFF TODAY

Duration6 days

From

USD 3,855

USD 3,178

Saving

USD 677

View Tour

Venice, North Lakes & Milan - 8 Days - September 2026

18% OFF TODAY

Halloween Super Sales

Venice, North Lakes & Milan - 8 days - September 2026

No booking fees

Best price guaranteed

Experience the beauty of northern Italy on this 8-day Italy group tour from Venice to Milan. Begin with canals, cicchetti and the landmarks of Venice before heading to romantic Verona and the wine country of Franciacorta. Explore Bergamo with day trips to shimmering Lake Garda and postcard-perfect Lake Como, where a boat ride to Bellagio is a highlight. In Switzerland, board the Bernina Express for one of Europe’s most scenic train rides through the Alps. The trip ends in stylish Milan, with time to explore its cathedrals, galleries and buzzing café culture.

Explorer

Tour Type

Group Tour

Accommodation

Hotel, Luxury Hotel, Resort

Age Range

18-80 yrs

Operated in

english

Destinations

Milan, Venice, Bergamo

18% OFF TODAY

Duration8 days

From

USD 3,825

USD 3,154

Saving

USD 671

View Tour

Milan, Liguria & Venice - 8 Days - September 2026

18% OFF TODAY

Halloween Super Sales

Milan, Liguria & Venice - 8 days - September 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

18% OFF TODAY

Duration8 days

From

USD 4,365

USD 3,599

Saving

USD 766

View Tour

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

18% OFF TODAY

Halloween Super Sales

Italian Lakes, Alps & Dolomites - 9 days - September 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

View Tour

Halloween Super Sales

Rome Revealed: A Classic City Break - September 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 803

USD 779

Saving

USD 24

View Tour

8% OFF TODAY

Halloween Super Sales

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

8% OFF TODAY

Duration15 days

From

USD 3,031

USD 2,793

Saving

USD 238

View Tour

Halloween Super Sales

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

USD 1,586

Saving

USD 49

View Tour

Halloween Super Sales

Icons of Italy: Rome to Milan - September 2026

Trip customizable

Best price guaranteed

Discover the soul of Italy on this perfectly paced 8-day journey from Rome to Milan. Begin your adventure amid the ancient ruins of the Eternal City, step into the heart of Renaissance Florence, glide through Venice’s enchanting canals by gondola, and cap off your experience in the stylish streets of Milan. With guided tours, scenic high-speed trains, and time to explore at your own pace, this tour offers the ideal blend of cultural discovery, iconic landmarks, and authentic Italian charm. Let Italy’s timeless beauty unfold before you—one unforgettable moment at a time

Explorer

Tour Type

Private Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Milan, Rome, Colosseum, Florence

Milan, Rome, Colosseum, Florence, Venice

Duration8 days

From

USD 1,864

USD 1,808

Saving

USD 56

View Tour

All Milan Tours in September 2026

Page 2 of 45 Trips in Milan during September 2026 with 558 Reviews

Get a customized trip to Milan in September 2026

Central & Western Europe: Classic Cities - September 2026

Venice to Milan - 13 days - September 2026

Venice to Liguria Loop - 11 days - September 2026

Scenic Italy & Switzerland - 13 days - September 2026

Rome to Milan Encompassed - 17 days - September 2026

Rome to Florence, Alps & Dolomites - 13 days - September 2026

Milan to Venice & the Dolomites - 6 days - September 2026

Venice, North Lakes & Milan - 8 days - September 2026

Milan, Liguria & Venice - 8 days - September 2026

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

Rome Revealed: A Classic City Break - September 2026

Simply Italy 35 to 45 - September 2026

Paris to Rome by Train - September 2026

Icons of Italy: Rome to Milan - September 2026

Page 2 of 45 Trips in Milan during September 2026 with 558 Reviews

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 2 of 45 Trips in Milan during September 2026 with 558 Reviews

Get a customized trip to Milan in September 2026

Page 2 of 45 Trips in Milan during September 2026 with 558 Reviews