10 Best Milan Multiday Tours in May 2026

Alpine Elegance: Small Group Tour to the Dolomites - May 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 3,539

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Northern Lakes & the Dolomites with Bernina Expres - May 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 4,704

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Italy’s Lakes & Bernina Express: Small Group Tour - May 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 2,677

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Classic Italy & the Dolomites - May 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 4,994

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Icons of Italy: Rome to Milan - May 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 1,881

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Italian Lakes & Northern Gems Escape - May 2026

Trip customizable

Best price guaranteed

From the shimmering canals of Venice to the alpine beauty of Lake Maggiore and the stylish streets of Milan, this thoughtfully curated journey showcases the elegance and diversity of Northern Italy. Stay in hand-picked 4-star hotels, enjoy expert-guided tours through historic cities like Verona and Venice, and unwind with wine tastings, island cruises, and scenic drives through vineyard-covered hills. With a perfect balance of immersive experiences and free time to explore at your own pace—all seamlessly organized—this is more than a trip; it’s a journey into the heart of Italy’s beauty

Explorer

Tour Type

Group Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Milan, Venice, Verona, Lake Magg

Milan, Venice, Verona, Lake Maggiore, Lake Como

Duration8 days

From

USD 2,098

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A Taste of Medieval Italy - May 2026

No booking fees

Best price guaranteed

Step into Italy’s enchanting Emilia-Romagna region: a place where every recipe is a story and every lovely vista is destined to become ingrained on your memory for eternity. Our 9-day journey meanders lazily through this extraordinary region, taking in timeless hilltop towns, cities that glimmer with medieval treasures and rustic castle estates where culinary traditions abound. If food is the key to your heart, prepare to fall head over heels on this carefully crafted Italian escape...

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

18-80 yrs

Operated in

english

Destinations

Milan, Parma, Bologna, Ravenna

Milan, Parma, Bologna, Ravenna, Padova

Duration9 days

From

USD 3,999

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Irresistible Italy: Rome to Venice - May 2026

Trip customizable

Best price guaranteed

Unveil Italy’s splendor with a 12-day journey through Rome, Florence, La Spezia, Milan, and Venice. Indulge in a wine tasting in Chianti, a private transfer from Rome’s airport, and captivating guided tours of the Colosseum, Roman Forum, and Pompeii. Discover Tuscany’s charm on a coach tour, revel in the scenic Cinque Terre with a 48-hour Train Card and embrace the elegance of Lake Como with unlimited boat trips. Savor a gondola ride in Venice and glide through high-speed train adventures across Italy’s iconic landscapes

Explorer

Tour Type

Private Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice, Colosseu

Rome, Florence, Venice, Colosseum, La Spezia, Cinque Terre, Milan, Lake Como

Duration12 days

From

USD 3,155

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Unforgettable Gems of Italy - May 2026

Trip customizable

Best price guaranteed

Embark on a timeless journey through Italy, where history, art, and natural beauty converge. From the ancient grandeur of Rome, with its iconic Colosseum and the Vatican's awe-inspiring masterpieces, to the romantic allure of the Amalfi Coast, where sun-kissed beaches and charming villages line the coastline. Immerse yourself in the heart of Tuscany, renowned for its world-class wines, picturesque landscapes, and historic cities like Florence and Siena. Discover the Cinque Terre, a collection of five colorful villages perched on cliffs overlooking the Ligurian Sea, offering breathtaking views and quaint charm. This extraordinary tour offers a perfect blend of history, culture, and natural beauty, promising unforgettable memories.

Art and architecture

Tour Type

Private Tour

Age Range

1-99 yrs

Operated in

English

Destinations

Rome, Amalfi Coast & Campania, F

Rome, Amalfi Coast & Campania, Florence, Venice, The Vatican, Montepulciano, Naples, Tuscany, Lucca, Cinque Terre, Milan, Lake Como, Tivoli, Vatican City, Pompeii, Amalfi Coast, Capri

Duration22 days

From

USD 9,195

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15% OFF TODAY

Super Sales

Milan City Break - May 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

15% OFF TODAY

Duration4 days

From

USD 352

USD 299

Saving

USD 53

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Super Sales

Europe by Rail Budapest to Milan - May 2026

(18 reviews )

No booking fees

Best price guaranteed

The trip was amazing. Our tour guide Rhyannon always made sure we were looked after, took us to the best recommendations, and went above and beyond to make sure we have the best experience. I would travel with her again as our guide!

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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All Milan Tours in May 2026

Page 3 of 39 Trips in Milan during May 2026 with 428 Reviews

Page 3 of 39 Trips in Milan during May 2026 with 428 Reviews

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

Northern Lakes & the Dolomites with Bernina Expres - May 2026

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

Classic Italy & the Dolomites - May 2026

Icons of Italy: Rome to Milan - May 2026

Italian Lakes & Northern Gems Escape - May 2026

A Taste of Medieval Italy - May 2026

Irresistible Italy: Rome to Venice - May 2026

Unforgettable Gems of Italy - May 2026

Milan City Break - May 2026

Europe by Rail Budapest to Milan - 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

Page 3 of 39 Trips in Milan during May 2026 with 428 Reviews

Page 3 of 39 Trips in Milan during May 2026 with 428 Reviews