10 Best Italy Multiday Tours in May 2026

Get a customized trip to Italy in May 2026

Plan a multi-country or regional adventure across Italy in May 2026, with help from a local expert.

Alessandra GalassiTravel Expert in Italy
Elena KyrimiTravel Expert in Greece & Italy
Danilo CataniaTravel Expert in Italy

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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.

Combine Italy in May with Nearby Countries for an Unforgettable Trip

See tours with itineraries going through multiple countries, including Italy

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Alternatively, explore tours that are exclusively just Italy and Spain, Germany and Italy or France and Italy.

13% OFF TODAY

Black Week Super Sales

Italian Discovery - May 2026

4.8

(90 reviews )

No booking fees

Best price guaranteed

Italy was a fantastic trip for us. Wonderful fellow travelers and a first-rate guide. We were able to see and do things that would not have been easily accessible to a large group or individuals, and it was a fantastic balance between structure and free time. Strongly advised

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

6-80 yrs

Operated in

english, spanish

Destinations

Rome, Florence, Venice, Naples

Rome, Florence, Venice, Naples, Lazio, Sorrento

13% OFF TODAY

Duration11 days

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21% OFF TODAY

Black Week Super Sales

Taste of Italy - May 2026

4.6

(57 reviews )

No booking fees

Best price guaranteed

I recently had the opportunity to embark on a wonderful tour of Italy, and it was an experience that will forever hold a special place in my heart. From the moment I set foot in this beautiful country, I was captivated by its rich history, stunning landscapes, and warm hospitality. Our journey began in Rome, where ancient ruins like the Colosseum and the Roman Forum transported us back in time. The grandeur of the Vatican City left me in awe, especially when I gazed upon Michelangelo's masterpiece, the Sistine Chapel ceiling. As we ventured north to Florence, I was enchanted by the art and culture of Tuscany. The Uffizi Gallery and Florence Cathedral were absolute highlights, and strolling along the Arno River at sunset was a truly romantic experience. Our tour continued to Venice, where the intricate canals and ornate architecture made me feel like I was in a fairytale. A gondola ride through the narrow waterways was a dream come true, and exploring the historic neighborhoods of San Marco and Dorsoduro was a delight.

Food toursCity sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

10-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice, Cinque Terre

21% OFF TODAY

Duration7 days

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32% OFF TODAY

Black Week Super Sales

Italy City Break - 5 Days - May 2026

4.5

(4 reviews )

Trip customizable

Best price guaranteed

Exploring Italy through this trip was an unforgettable experience! It allowed us to see all the iconic landmarks in each city we visited, offering a remarkable variety of activities that left no room for boredom. What made the journey even more exceptional were the guides - their passion for the country, combined with their extensive knowledge, made the trip truly unforgettable. They made it a priority to connect with each and every traveler, ensuring that everyone was fully immersed in the tour. With everything taken care of, this trip exceeded our expectations and more. I highly recommend it to anyone who wants to discover Italy in the best possible way!

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice, Assisi

Rome, Florence, Venice, Assisi, Montepulciano, Siena, Tuscany, Bologna, Padua

32% OFF TODAY

Duration5 days

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18% OFF TODAY

Best Seller

Black Week Super Sales

Rome to Amalfi - May 2026

No booking fees

Best price guaranteed

If you want a short trip packed with historic sites and delicious bites, this eight-day adventure fits the bill. Get to know Italy's 'Eternal City' (Rome), hike up Mt Vesuvius volcano on the Bay of Naples and witness the aftermath of the 79 AD eruption on a guided tour of Pompeii. Then soak up the sunshine in the coastal town of Sorrento, taste limoncello from the source and hike along the beautiful Amalfi Coast. With archaeological sites, gelato making workshops, pizza tastings and a local leader to share their culture, you're all set for a taste of la dolce vita.

City sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel, Resort, Hut

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Amalfi Coast & Campania, P

Rome, Amalfi Coast & Campania, Pompeii, Sorrento, Amalfi

18% OFF TODAY

Duration8 days

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13% OFF TODAY

Black Week Super Sales

Italian Holiday - May 2026

4.6

(10 reviews )

No booking fees

Best price guaranteed

We enjoyed the work of director and her driver.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, The Vatican, Venice, Veron

Rome, The Vatican, Venice, Verona, Florence

13% OFF TODAY

Duration7 days

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24% OFF TODAY

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Europe Jewel - May 2026

4.9

(145 reviews )

No booking fees

Best price guaranteed

This is a fast pace tour so we've seen many points of interests in 11 counties in 14 days. It was well organized and learned some of the countries history, which was very nice. Pascal is such a caring person and excellent driver. He always have that beautiful smile and warm hello whenever he sees you even though he worked for many long hours. Would give him 7 stars out of 5. He goes above and beyond expectations. What an asset forExpat! Matt is very well versed in European history and it is great learning from him. He also kept us well informed so that the tour runs smoothly, which we appreciate very much. Though a couple of the hotels are not up to par, it won't prevent us from touring through Expat in the future. Overall, it was a great experience for us .

Art and architecture

Tour Type

Group Tour

Accommodation

Hotel

Age Range

10-99 yrs

Operated in

english

Destinations

Amsterdam, Ghent, Swiss Alps, Pa

Amsterdam, Ghent, Swiss Alps, Paris, Rhine, Prague, Vienna, Budapest, Ljubljana, Venice, Tuscany

24% OFF TODAY

Duration14 days

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13% OFF TODAY

Black Week Super Sales

Best of Italy - May 2026

3.2

(6 reviews )

No booking fees

Best price guaranteed

We highly recommend this Best of Italy tour!!! This tour is a great introduction to Italy and includes the key highlights of this beautiful country. Booking through Bookmundi was easy & the discount appreciated

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Florence, Sorrento, Assisi

Rome, Florence, Sorrento, Assisi, Venice, Varese

13% OFF TODAY

Duration13 days

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8% OFF TODAY

Black Week Super Sales

Italy and Switzerland - May 2026

4.5

(14 reviews )

No booking fees

Best price guaranteed

Every thing was good hotels in Zurich was perfect also in Roma and very very thanks to our tour guide she’s name is Eva she was the best of our trip and I hope I will go all my tours with europmound and with Eva 🤍🌹

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice, Zurich

Rome, Florence, Venice, Zurich, Milan

8% OFF TODAY

Duration9 days

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Explore Malta 5 Days, Self-drive - May 2026

22% OFF TODAY

Black Week Super Sales

Explore Malta 5 Days, Self-drive - May 2026

Trip customizable

Best price guaranteed

Discover the best of Malta during this short self-drive tour! Walk through the streets of La Valletta, often referred to as “the city built by gentlemen for gentlemen”, the capital of Malta offers both culture and relaxation. Visit the famous Mosta Basilica, which is the third-largest in Europe and one of the main highlights of Malta.

Art and architecture

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Sliema, St Julian's, Sliema

22% OFF TODAY

Duration5 days

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8% OFF TODAY

Black Week Super Sales

Treasures of Italy - May 2026

4.4

(7 reviews )

No booking fees

Best price guaranteed

It is good that Miguel is also recommending restaurants to dine in, they have good price, good food and good service.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Venice, Perugia, Siena, Fl

Rome, Venice, Perugia, Siena, Florence, Genoa, Milan, Verona

8% OFF TODAY

Duration13 days

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Italy Tours in May 2026

Get a customized trip to Italy in May 2026

See Italy tours by duration

Get a customized trip to Italy in May 2026

Page 2 of 252 Trips in Italy during May 2026 with 38,734 Reviews

Page 2 of 252 Trips in Italy during May 2026 with 38,734 Reviews

Combine Italy in May with Nearby Countries for an Unforgettable Trip

Italian Discovery - May 2026

Taste of Italy - May 2026

Italy City Break - 5 Days - May 2026

Rome to Amalfi - May 2026

Italian Holiday - May 2026

Europe Jewel - May 2026

Best of Italy - May 2026

Italy and Switzerland - May 2026

Explore Malta 5 Days, Self-drive - May 2026

Treasures 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

Italy Tours in May 2026

Get a customized trip to Italy in May 2026

See Italy tours by duration

Get a customized trip to Italy in May 2026

Page 2 of 252 Trips in Italy during May 2026 with 38,734 Reviews

Page 2 of 252 Trips in Italy during May 2026 with 38,734 Reviews