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All Italy Tours in May 2027

Planning for a trip to Italy during May? We offer 240 tour packages to Italy departing in May 2027 that have 6,300 customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Italy on your May holiday.

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All Italy Tours in May 2027

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

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Showing 1 - 10 of 253 results

Duration

1 day26 days

Day Tour
Multiday Tour

Price

USD 31USD 10,299

Budget Tours
Luxury Tours

Tour Types

Group Tours
Small Group Tours
Solo-friendly Group Tours
Solo-only Group Tours
Private Tours

Age

Young Travelers (Age 18-39)Mature Travelers (Age 40-59)Senior Travelers (Age 60+)

Activities

Cultural, religious and historic sites
City sightseeing
Art and architecture
Walking tours
Explorer

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
Venice
Florence
Naples
Sorrento

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Guide Types

Guided Tours
Self Guided Tours
Partially Guided Tours

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See Italy tours by duration

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

Duration

1 day26 days

Day Tour
Multiday Tour

Tour Types

Group Tours
Small Group Tours
Solo-friendly Group Tours
Solo-only Group Tours
Private Tours

Activities

Cultural, religious and historic sites
City sightseeing
Art and architecture
Walking tours
Explorer

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
Venice
Florence
Naples
Sorrento

Guide Types

Guided Tours
Self Guided Tours
Partially Guided Tours

Get a customized trip to Italy in May 2027

Plan a multi-country or regional adventure across Italy in May 2027, 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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Start & End Location

Price

USD 31USD 10,299

Budget Tours
Luxury Tours

Page 8 of 253 Trips in Italy during May 2027 with 6,335 Reviews

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 Switzerland, France and Italy or England and Italy.

Upgraded - Walking Italy: Rome & Umbria - May 2027

4.7

(3 reviews )

No booking fees

Best price guaranteed

A very pleasant and enjoyable holiday with great accommodation, views ,walks and guides. Enrico our rep was fantastic. Friendly, funny and engaging...

Walking toursCity sightseeing

Tour Type

Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers

Accommodation

Hotel, Resort

Age Range

16-99 yrs

Operated in

english

Destinations

Rome, Colosseum, Umbria, Bevagna

Rome, Colosseum, Umbria, Bevagna, Spoleto, Orvieto

Duration8 days

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Splendours of Italy - May 2027

(13 reviews )

No booking fees

Best price guaranteed

It was well worth the money and we enjoyed the optional experience . We weren’t always happy with the hotel choice but any issues we had the direct...

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Florence, Bay Of Naples, A

Rome, Florence, Bay Of Naples, Assisi, Venice, Milan

Duration13 days

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Country Roads of Tuscany & Central Italy - May 2027

4.4

(18 reviews )

No booking fees

Best price guaranteed

This is for athletic people. You have to be able to walk long distances at a time and up STEEP roads. It is a physical workout. Not for anyone with...

Museum and gallery visits

Tour Type

Group Tour

Accommodation

Hotel, Villa, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice

Duration9 days

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Explore Southern Sicily - May 2027

(8 reviews )

No booking fees

Best price guaranteed

Sicily is an extraordinary place and this trip really made me feel I got the most out of it in the time I had.

Cultural, religious and historic sites

Tour Type

Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers

Accommodation

Hotel, Villa

Age Range

12-100 yrs

Operated in

english

Destinations

Palermo, Catania, Syracuse, Agri

Palermo, Catania, Syracuse, Agrigento, Trapani

Duration8 days

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Tuscany to Cinque Terre: Wines, Villages & Unforgettable Walks - May 2027

(7 reviews )

No booking fees

Best price guaranteed

I don't like planning trips and couldn't find a time that worked to travel with a friend, so decided to go on a group tour, and this trip was a gre...

Sightseeing Tours

Tour Type

Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers

Accommodation

Hotel, Villa

Age Range

12-100 yrs

Operated in

english

Destinations

Florence, Cinque Terre, Chianti

Duration7 days

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Italian Holiday - May 2027

4.7

(67 reviews )

No booking fees

Best price guaranteed

We greatly enjoyed the Italian Holiday! Anna was an excellent travel director. Our group was diverse but quickly became friends. Pepe was an excell...

Explorer

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, Verona, Florence

Duration7 days

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Tuscan Adventure: Rome to Florence - May 2027

(4 reviews )

No booking fees

Best price guaranteed

It was great and I am really glad I did it through a travel company, because planning it on my own would have taken so much time that i probably wo...

Explorer

Tour Type

Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers

Accommodation

Villa, Hotel

Age Range

12-100 yrs

Operated in

english

Destinations

Rome, Florence, Montepulciano

Duration7 days

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Italian Apennines: Walks & Wildlife - May 2027

(5 reviews )

No booking fees

Best price guaranteed

This trip on Rewilding the Apennines took us on incredible walks to magnificent views that made us feel we were the only people on earth. We had th...

Trekking and HikingWildlife

Tour Type

Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers

Accommodation

Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Rome, Pescasseroli

Duration6 days

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Enchanting Southern Italy - May 2027

4.7

(129 reviews )

No booking fees

Best price guaranteed

This was the perfect way to see the southern Italy / Amalfi Coast, the 5 nights in Minori was a great location to return to each evening. Our visit...

Explorer

Tour Type

Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers

Accommodation

Villa, Hotel

Age Range

18-80 yrs

Operated in

english

Destinations

Naples, Castellabate, Minori

Duration8 days

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Simply Italy - May 2027

(6 reviews )

No booking fees

Best price guaranteed

It was cool that we got to see so much of the beautiful country and making new friends along the way. It would have been nice to spend longer in ce...

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

Duration15 days

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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

Hi there

All Italy Tours in May 2027

All Italy Tours in May 2027

See Italy tours by duration

Get a customized trip to Italy in May 2027

Page 8 of 253 Trips in Italy during May 2027 with 6,335 Reviews

Page 8 of 253 Trips in Italy during May 2027 with 6,335 Reviews