10 Best Milan Multiday Tours in May 2026

Get a customized trip to Milan in May 2026

Plan a multi-country or regional adventure across Milan in May 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.

23% OFF TODAY

Halloween Super Sales

Italian Intermezzo - May 2026

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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18% OFF TODAY

Halloween Super Sales

Discovering Milan - May 2026

(1 review )

Trip customizable

Best price guaranteed

Join this four-day short break in Milan and discover Sforza Castle the most impressive urban castle in Europe, and Duomo Cathedral, a striking example of Gothic art and the largest church in Italy. Admire the famous Last Supper of Leonardo Da Vinci, enjoy the Navigli district and take a trip to Lake Como and Lugano. Don’t miss the shopping opportunity as Milan is one of the most important cities in the world of fashion.

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

6-99 yrs

Operated in

english

Destinations

Milan

18% OFF TODAY

Duration4 days

From

USD 810

USD 668

Saving

USD 142

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Northern Italian Lakes & Countryside - May 2026

20% OFF TODAY

Halloween Super Sales

Northern Italian Lakes & Countryside - May 2026

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

20% OFF TODAY

Duration9 days

From

USD 2,725

USD 2,189

Saving

USD 536

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Country Roads Of Northern Italy - May 2026

14% OFF TODAY

Halloween Super Sales

Country Roads of Northern Italy - May 2026

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 - May 2026

17% OFF TODAY

Halloween Super Sales

Northern Italy Including Cinque Terre - May 2026

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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Halloween Super Sales

Lake Como Walking - May 2026

4.9

(25 reviews )

No booking fees

Best price guaranteed

Great hotel, good challenging walks and beautiful scenery.

Active and outdoor

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

16-79 yrs

Operated in

english

Destinations

Milan, Gravedona, Livo, Sorico

Milan, Gravedona, Livo, Sorico, Bellagio, Como, Dongo

Duration8 days

From

USD 2,490

USD 2,415

Saving

USD 75

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Halloween Super Sales

Jewels of Italy and Milan by Rail - May 2026

(1 review )

Trip customizable

Best price guaranteed

I’ve always loved Italy, but doing it by rail added a special touch. Over eight days, we hit Rome, Florence, Venice, and wrapped up in Milan, all by high-speed train. The pace worked perfectly for me (I’m 58), with fresh city arrivals each morning and comfortable hotels each night The highlights: a hop-on hop-off loop in Rome hit the Colosseum, Pantheon, Trevi Fountain , an optional wine tasting tour that I booked in Florence and Venice’s gondola ride. Everything flowed perfectly well..no dragging suitcases or missed trains. For travelers in our age bracket, this tour blends comfort, culture, and hassle-free travel. If you want Italy’s treasures without the planning headache, this rail tour delivers in a big way.

City sightseeingTrain tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

english

Destinations

Milan, Rome, Florence, Venice

Duration8 days

From

USD 1,417

USD 1,374

Saving

USD 43

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20% OFF TODAY

Halloween Super Sales

Italian Glory - May 2026

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

20% OFF TODAY

Duration13 days

From

USD 4,575

USD 3,665

Saving

USD 910

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Halloween Super Sales

Reflections of Italy - May 2026

4.8

(145 reviews )

No booking fees

Best price guaranteed

The whole experience was a wonderful safe experience. Lots of walking the food was good and the culture was thought and the whole tour was an educational experience.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Milan, Rome, Lake Como, Perugia

Milan, Rome, Lake Como, Perugia, Florence, Venice

Duration10 days

From

USD 2,949

USD 2,861

Saving

USD 88

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27% OFF TODAY

Halloween Super Sales

Simply Italy - May 2026

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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Halloween Super Sales

Essential Portugal, Spain, Switzerland and Italy - May 2026

(4 reviews )

Trip customizable

Best price guaranteed

Four amazing countries in one trip! Each place had its own unique charm, and the itinerary was perfectly balanced. Switzerland’s Alps and Italy’s gelato were highlights!

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

8-99 yrs

Operated in

english

Destinations

Lisbon, Rome, Zurich, Mont Blanc

Lisbon, Rome, Zurich, Mont Blanc, Milan, Madrid, Barcelona, Girona, Leysin

Duration13 days

From

USD 2,309

USD 2,240

Saving

USD 69

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8% OFF TODAY

Halloween Super Sales

Ultimate Italy - May 2026

(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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27% OFF TODAY

Halloween Super Sales

Italian Espresso - May 2026

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

View Tour

13% OFF TODAY

Halloween Super Sales

Splendours of Italy - May 2026

(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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All Milan Tours in May 2026

40 Trips in Milan during May 2026 with 558 Reviews

Get a customized trip to Milan in May 2026

40 Trips in Milan during May 2026 with 558 Reviews

Italian Intermezzo - May 2026

Discovering Milan - May 2026

Northern Italian Lakes & Countryside - May 2026

Country Roads of Northern Italy - May 2026

Northern Italy Including Cinque Terre - May 2026

Lake Como Walking - May 2026

Jewels of Italy and Milan by Rail - May 2026

Italian Glory - May 2026

Reflections of Italy - May 2026

Simply Italy - May 2026

Essential Portugal, Spain, Switzerland and Italy - May 2026

Ultimate Italy - May 2026

Italian Espresso - May 2026

Splendours of Italy - May 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 May 2026

40 Trips in Milan during May 2026 with 558 Reviews

Get a customized trip to Milan in May 2026

40 Trips in Milan during May 2026 with 558 Reviews