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 814

USD 671

Saving

USD 143

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Northern Italian Lakes & Countryside - May 2026

18% 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

18% OFF TODAY

Duration9 days

From

USD 2,725

USD 2,239

Saving

USD 486

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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

Reflections of Italy - May 2026

4.8

(146 reviews )

No booking fees

Best price guaranteed

I can't say enough about our guide, Daniel. He ensured our trip we had the best time. I learned so much from him about the places we visited and some we didn't. I would definitely request Daniel for future tours with Collette. I loved all the places on this route. I would like to stay an extra day in one of the hill towns like Cortona. One of my favorite experiences visiting the winery and the cooking class at Castello del Trebbio.

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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18% OFF TODAY

Halloween Super Sales

North Of Italy, Private Tour - May 2026

(1 review )

Trip customizable

Best price guaranteed

One week custom private tour in northern Italy was outstanding overall. tour director, hotels, day trips, transport were excellent.

Art and architecture

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, spanish, french, german, italian

Destinations

Milan, Venice, Verona, Como

18% OFF TODAY

Duration8 days

From

USD 2,623

USD 2,163

Saving

USD 460

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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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18% OFF TODAY

Halloween Super Sales

Classic Italy, Private Tour - May 2026

(1 review )

Trip customizable

Best price guaranteed

Drive through some of Italy's most iconic locations on this six-day tour that takes you through Florence, Siena, Verona, Venice, Sirmione and Milan. Considered the birthplace of the Renaissance, Florence breathes history at every corner, while Venice will enchant you with its shimmering canals.

Art and architecture

Tour Type

Private Tour

Accommodation

Hotel, Villa

Age Range

6-99 yrs

Operated in

english, spanish, french, german, italian

Destinations

Florence, Venice, Milan

18% OFF TODAY

Duration6 days

From

USD 2,765

USD 2,280

Saving

USD 485

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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

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8 Days Art Cities Of Italy, Private Tour - May 2026

18% OFF TODAY

Halloween Super Sales

8 Days Art Cities Of Italy, Private Tour - May 2026

(1 review )

Trip customizable

Best price guaranteed

They did a great job with everything!

Art and architectureHoneymoon

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, spanish, french, german, italian

Destinations

Rome, Florence, Venice, Milan

18% OFF TODAY

Duration8 days

From

USD 3,344

USD 2,757

Saving

USD 587

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In The Footsteps Of Leonardo: 7 Days From Venice To Florence, Private Tour - May 2026

18% OFF TODAY

Halloween Super Sales

In The Footsteps Of Leonardo: 7 Days From Venice To Florence, Private Tour - May 2026

Trip customizable

Best price guaranteed

Join our seven days tour for a “full immersion” into Leonardo Da Vinci’s life. Visit Accademia Gallery in Venice, Cenacolo and Pinacoteca Ambrosiana in Milan and Uffizi Gallery in Florence. Our expert guides will lead you to the most important sites of these cities to show you the famous masterpieces of this amazing artist and his life.

Art and architecture

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english, spanish, french, german, italian

Destinations

Florence, Venice, Milan

18% OFF TODAY

Duration7 days

From

USD 1,972

USD 1,626

Saving

USD 346

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Halloween Super Sales

Rome Florence Venice Milan and Lake Como by Rail - May 2026

(1 review )

Trip customizable

Best price guaranteed

This train tour across Italy allows you to explore some of the nation’s most prominent landmarks. It starts with Rome which is the foundation of Christian culture and Western civilization. When here, you can visit the Roman Colosseum, Navona Square, Trevi Fountain, St Peter's Basilica and the Vatican Museum. The next stop of this journey is Florence, the capital city of Tuscany. Known for Michelangelo’s David sculpture and taking you through chapters of the renaissance period one by one, Florence is a paradise for people loving art and history. Up next is the City of Canals, Venice. Believed to be of the most romantic cities in the world, Venice also boasts of Doge’s Palace and San Marco Square. The fourth destination of this tour is Milan, Italy’s fashion capital. Apart from being captivated by the stylish Milan streets, you can also explore the Duomo, the Castello Sforzesco, and the famous Navigli canals. Fifth in the line is the place of dreams, Lake Como. Renowned for fabulous lakeside resorts, fine dining restaurants, and alluring beauty, this place will take your breath away! Post this, you will travel back to Milan, coming to the end of one of our Scenic tours of Italy.

Train tours

Tour Type

Independent Tour

Accommodation

Hotel, Resort

Age Range

8-99 yrs

Operated in

English

Destinations

Rome, Lake Como, Milan, Florence

Rome, Lake Como, Milan, Florence, Venice

Duration11 days

From

USD 1,312

USD 1,273

Saving

USD 39

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Enchanting Waters: Discovering The Lakes Of Italy, Self-drive - May 2026

18% OFF TODAY

Halloween Super Sales

Enchanting Waters: Discovering The Lakes Of Italy, Self-drive - May 2026

Trip customizable

Best price guaranteed

Choose this self-drive tour in the Lombardy region and spend 8 memorable days exploring the beautiful landscapes and culture of Italy. Visit mesmerising lakes of Maggiore, Como and Garda, take a boat to Bellagio and admire the beauty and tranquillity of the scenery that surrounds you. Walk through the medieval streets of Bergamo and visit Verona, a city full of history. This trip will fill all your senses and will leave great memories for a lifetime.

Self-drive or vehicle rental

Tour Type

Private Tour

Accommodation

Hotel, Villa

Age Range

6-99 yrs

Operated in

english

Destinations

Milan, Lake Maggiore, Lake Garda

18% OFF TODAY

Duration8 days

From

USD 1,710

USD 1,410

Saving

USD 300

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All Milan Tours in May 2026

17 Trips in Milan during May 2026 with 393 Reviews

Get a customized trip to Milan in May 2026

Italian Intermezzo - May 2026

Discovering Milan - May 2026

Northern Italian Lakes & Countryside - May 2026

Northern Italy Including Cinque Terre - May 2026

Reflections of Italy - May 2026

North Of Italy, Private Tour - May 2026

Simply Italy - May 2026

Classic Italy, Private Tour - May 2026

Ultimate Italy - May 2026

Italian Espresso - May 2026

8 Days Art Cities Of Italy, Private Tour - May 2026

In The Footsteps Of Leonardo: 7 Days From Venice To Florence, Private Tour - May 2026

Rome Florence Venice Milan and Lake Como by Rail - May 2026

Enchanting Waters: Discovering The Lakes Of Italy, Self-drive - May 2026

17 Trips in Milan during May 2026 with 393 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 May 2026

17 Trips in Milan during May 2026 with 393 Reviews

Get a customized trip to Milan in May 2026

17 Trips in Milan during May 2026 with 393 Reviews