10 Best Milan Multiday Tours in September 2027

Get a customized trip to Milan in September 2027

Plan a multi-country or regional adventure across Milan in September 2027, 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.

23% OFF TODAY

Halloween Super Sales

Italian Intermezzo - September 2027

4.6

(68 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

23% OFF TODAY

Duration8 days

From

USD 2,595

USD 2,008

Saving

USD 587

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Northern Italian Lakes & Countryside - September 2027

18% OFF TODAY

Halloween Super Sales

Northern Italian Lakes & Countryside - September 2027

3.9

(48 reviews )

No booking fees

Best price guaranteed

This tour took us to some amazing destinations. Our tour director, and our bus operator were absolutely exceptional.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort, Lodge

Age Range

5-99 yrs

Operated in

english

Destinations

Milan, Baveno, Bergamo, Verona

Milan, Baveno, Bergamo, Verona, Mantua, Garda, Modena

18% OFF TODAY

Duration9 days

From

USD 2,725

USD 2,239

Saving

USD 486

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Country Roads Of Northern Italy - September 2027

14% OFF TODAY

Halloween Super Sales

Country Roads of Northern Italy - September 2027

4.5

(48 reviews )

No booking fees

Best price guaranteed

Keep the flexibility of the add on activities.

AdventureCity sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Milan, Trento, Lake Maggiore

14% OFF TODAY

Duration10 days

From

USD 3,695

USD 3,182

Saving

USD 513

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Northern Italy Including Cinque Terre - September 2027

17% OFF TODAY

Halloween Super Sales

Northern Italy Including Cinque Terre - September 2027

4.5

(98 reviews )

No booking fees

Best price guaranteed

Very enjoyable, with a variety of interesting locations.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Milan, Baveno, Italian Riviera

Milan, Baveno, Italian Riviera, Cinque Terre, Lake Maggiore

17% OFF TODAY

Duration8 days

From

USD 2,395

USD 1,976

Saving

USD 419

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15% OFF TODAY

Halloween Super Sales

Italian Glory - September 2027

4.8

(55 reviews )

No booking fees

Best price guaranteed

Great itinerary and tour director. Suggest: a slightly slower pace - limiting yourself to 1 optional experience/ day to avoid too/ long days -exhaustion, provide more suggestions for authentic food / restaurants on ‘free’ days.

Chill outSightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Milan, Rome, Lake Como, Como, Ve

Milan, Rome, Lake Como, Como, Venice, Florence, Amalfi Coast & Campania

15% OFF TODAY

Duration13 days

From

USD 4,575

USD 3,880

Saving

USD 695

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27% OFF TODAY

Halloween Super Sales

Simply Italy - September 2027

No booking fees

Best price guaranteed

Welcome to 15 days of pure Italian travel immersion. Covering Rome, Florence, 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. 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!

Cultural, religious and historic sites

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

27% OFF TODAY

Duration15 days

From

USD 2,893

USD 2,105

Saving

USD 788

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27% OFF TODAY

Halloween Super Sales

Italian Espresso - September 2027

No booking fees

Best price guaranteed

10 days of la dolce vita, pronto. This one is pure Italian travel, covering all the big bucket-list destinations of Venice, Florence & Rome, plus the smaller charms of Pisa, Verona, and Siena. We'll ooh and aah over antipasto & chianti, dine on regional specialities in local trattorias, boat through the canals and islands of Venice, and explore the architecturally magnificent city of Florence. Expect plenty of world-famous espresso & pizza on the way.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

18-35 yrs

Operated in

english

Destinations

Rome, Venice, Florence, Cinque T

Rome, Venice, Florence, Cinque Terre, Milan

27% OFF TODAY

Duration10 days

From

USD 2,047

USD 1,489

Saving

USD 558

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13% OFF TODAY

Halloween Super Sales

Splendours of Italy - September 2027

(27 reviews )

No booking fees

Best price guaranteed

Very organized with a professional tour director and Driver!

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Florence, Bay Of Naples, A

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

13% OFF TODAY

Duration13 days

From

USD 2,725

USD 2,361

Saving

USD 364

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8% OFF TODAY

Halloween Super Sales

Ultimate Italy - September 2027

(1 review )

No booking fees

Best price guaranteed

I met some amazing people and saw so many incredible sights in Italy! This trip exceeded my expectations!

Chill outAdventure

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

18-35 yrs

Operated in

english

Destinations

Rome, Venice, Naples, Amalfi, Ca

Rome, Venice, Naples, Amalfi, Catania, Taormina, Syracuse, Cefalu, Florence, Palermo, Cinque Terre, Milan

8% OFF TODAY

Duration22 days

From

USD 4,648

USD 4,295

Saving

USD 353

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All Milan Tours in September 2027

9 Trips in Milan during September 2027 with 346 Reviews

Get a customized trip to Milan in September 2027

9 Trips in Milan during September 2027 with 346 Reviews

Italian Intermezzo - September 2027

Northern Italian Lakes & Countryside - September 2027

Country Roads of Northern Italy - September 2027

Northern Italy Including Cinque Terre - September 2027

Italian Glory - September 2027

Simply Italy - September 2027

Italian Espresso - September 2027

Splendours of Italy - September 2027

Ultimate Italy - September 2027

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 2027

9 Trips in Milan during September 2027 with 346 Reviews

Get a customized trip to Milan in September 2027

9 Trips in Milan during September 2027 with 346 Reviews