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All Italy Tours in May 2026

Planning for a trip to Italy during May? We offer 120 tour packages to Italy departing in May 2026 that have 1,100 customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Italy on your May holiday.

May 2026 Jun 2026 Jul 2026 Aug 2026 Sep 2026 Oct 2026 Nov 2026 Dec 2026 Jan 2027 Feb 2027 Mar 2027

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Duration
1 day24 days
- Day Tour
- Multiday Tour

Price
USD 31USD 6,990
- Budget Tours
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- Group Tours
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Age
- Young Travelers (Age 18-39)Mature Travelers (Age 40-59)Senior Travelers (Age 60+)
Activities
- Walking tours
- Explorer
- Trekking and Hiking
- Bicycle tours
- Cultural, religious and historic sites

Physical Rating
- relaxed
- easy
- moderate
- challenging

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.

Destinations
- Rome
- Florence
- Venice
- Naples
- Siena

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Showing 1 - 10 of 34 results

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

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Price

USD 31USD 6,990

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Page 4 of 34 Trips in Italy during May 2026 with 187 Reviews

Rome to Venice Italian Wonders Journey - 5 days - May 2026

No booking fees

Best price guaranteed

This enchanting 5-day journey kicks off in Rome, where you'll be whisked into the heart of this historic city. Explore the wonders of Imperial Rome...

Explorer

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-80 yrs

Operated in

english

Destinations

Rome, Venice, Florence

Duration5 days

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Italian Adventure Rome, Naples, Capri - 3 days - May 2026

No booking fees

Best price guaranteed

Kick off your 3-day Italian adventure from Rome to Naples, diving into a mix of culture, history, and jaw-dropping landscapes. In Naples, soak up t...

Explorer

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-80 yrs

Operated in

english

Destinations

Rome, Naples

Duration3 days

View Tour

Page 4 of 34 Trips in Italy during May 2026 with 187 Reviews

Roman Ruins to Swiss Peaks Adventure - 9 days - May 2026

No booking fees

Best price guaranteed

Start in the timeless city of Rome and end your 9-day adventure back in the Italian capital. Youï¿½ll discover the heart of Italy, beginning with R...

Explorer

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-80 yrs

Operated in

english

Destinations

Rome, Florence, Venice, Zurich

Rome, Florence, Venice, Zurich, Milan

Duration9 days

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Grand European Odyssey Rome to Milan - 8 days - May 2026

No booking fees

Best price guaranteed

Embark on an unforgettable 8-day adventure starting in the historic city of Rome and concluding back in the Eternal City. Youï¿½ll wander through R...

Explorer

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-80 yrs

Operated in

english

Destinations

Rome, Florence, Venice, Zurich

Rome, Florence, Venice, Zurich, Milan

Duration8 days

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Upcoming Departures

May 31

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May 31

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Food, wine, events and nightlife

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All Italy Tours in May 2026

See Italy tours by duration

Get a customized trip to Italy in May 2026

Page 4 of 34 Trips in Italy during May 2026 with 187 Reviews

Rome to Venice Italian Wonders Journey - 5 days - May 2026

Italian Adventure Rome, Naples, Capri - 3 days - May 2026

Page 4 of 34 Trips in Italy during May 2026 with 187 Reviews

Roman Ruins to Swiss Peaks Adventure - 9 days - May 2026

Grand European Odyssey Rome to Milan - 8 days - May 2026