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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15% OFF TODAY

Rome to Florence, Alps & Dolomites - 13 days - May 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

15% OFF TODAY

Duration13 days

From

USD 7,115

USD 6,048

Saving

USD 1,067

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15% OFF TODAY

Milan to Venice & the Dolomites - 6 days - May 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

15% OFF TODAY

Duration6 days

From

USD 3,865

USD 3,285

Saving

USD 580

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15% OFF TODAY

Venice, North Lakes & Milan - 8 days - May 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

15% OFF TODAY

Duration8 days

From

USD 3,825

USD 3,251

Saving

USD 574

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15% OFF TODAY

Milan, Liguria & Venice - 8 days - May 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

15% OFF TODAY

Duration8 days

From

USD 4,375

USD 3,719

Saving

USD 656

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18% 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

18% OFF TODAY

Duration4 days

From

USD 357

USD 294

Saving

USD 63

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15% OFF TODAY

Colosseum to Como - 12 days - May 2026

No booking fees

Best price guaranteed

Discover the heart of Italy and beyond on this 12-day journey from Rome to Milan. Begin with sightseeing of the Colosseum and Roman Forum in the Eternal City before travelling through Assisi, Siena and the Renaissance treasures of Florence. Enjoy Bologna’s food culture, glide through Venice’s canals, and wander Shakespearean Verona with a stop for wine tasting in Franciacorta. Highlights also include a boat trip on Lake Garda, the elegance of Lake Como, and a spectacular ride on Switzerland’s Bernina Express. Round your tour off in stylish Milan, with guided touring and free time to explore your way.

Explorer

Tour Type

Group Tour

Accommodation

Hotel, Luxury Hotel, Resort

Age Range

18-80 yrs

Operated in

english

Destinations

Milan, Rome, Florence, Venice, Bergamo

15% OFF TODAY

Duration12 days

From

USD 5,775

USD 4,909

Saving

USD 866

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15% OFF TODAY

Incredible Italy - 15 days - May 2026

No booking fees

Best price guaranteed

Discover Italy on a 15-day tour from Rome to Venice, weaving together history, scenery and flavour. Explore the Colosseum and Roman Forum, then journey through Assisi and Siena to Florence, the Renaissance jewel. Savour Bologna’s culinary traditions, enjoy a spritz in Venice, and admire fairytale Verona before cruising Lake Garda and Lake Como. Ride the Bernina Express through the Swiss Alps, taste wine in Liguria, and wander the colourful Cinque Terre. With iconic cities and hidden gems combined, this journey captures Italy at its finest.

Explorer

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

18-80 yrs

Operated in

english

Destinations

Rome, Venice, Milan, La Spezia

Rome, Venice, Milan, La Spezia, Florence, Bergamo

15% OFF TODAY

Duration15 days

From

USD 7,725

USD 6,566

Saving

USD 1,159

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15% OFF TODAY

Italian Highlights & Liguria - 11 days - May 2026

No booking fees

Best price guaranteed

Explore Italy’s cities, coastlines, and flavours on an 11-day journey with a scenic Swiss highlight. Wander Florence’s Renaissance landmarks, Siena’s medieval squares, and the timeless canals of Venice, while Milan blends history with modern style. Along the Ligurian coast, visit Santa Margherita Ligure, glamorous Portofino, and the colourful villages of Cinque Terre. In Emilia-Romagna, sample traditional balsamic vinegar and step into Ferrari’s world of speed. For a striking contrast, cross into Switzerland aboard the Bernina Express, gliding past glaciers and alpine peaks before returning to Italy’s charm-filled north.

Explorer

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

18-80 yrs

Operated in

english

Destinations

Rome, Venice, Florence, Milan, La Spezia

15% OFF TODAY

Duration11 days

From

USD 6,345

USD 5,393

Saving

USD 952

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15% OFF TODAY

Italian Lakes, Alps & Dolomites - 9 days - May 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

15% OFF TODAY

Duration9 days

From

USD 3,485

USD 2,962

Saving

USD 523

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5% OFF TODAY

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

5% OFF TODAY

Duration9 days

From

USD 3,999

USD 3,799

Saving

USD 200

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All Milan Tours in May 2026

Page 2 of 24 Trips in Milan during May 2026 with 280 Reviews

Get a customized trip to Milan in May 2026

Page 2 of 24 Trips in Milan during May 2026 with 280 Reviews

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

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

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

Milan, Liguria & Venice - 8 days - May 2026

Milan City Break - May 2026

Colosseum to Como - 12 days - May 2026

Incredible Italy - 15 days - May 2026

Italian Highlights & Liguria - 11 days - May 2026

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

A Taste of Medieval 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

Page 2 of 24 Trips in Milan during May 2026 with 280 Reviews

Get a customized trip to Milan in May 2026

Page 2 of 24 Trips in Milan during May 2026 with 280 Reviews