10 Best Italy Multiday Tours in May 2027

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Italy Bellissimo - May 2027

4.7

(220 reviews )

No booking fees

Best price guaranteed

Amazing variety of experiences, excellent tour guide and local specialists. I also loved that Trafalgar supports local artists and family run farms. A highlight for me was the Make Travel Matter experience with the weavers.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Capri, Assisi, Venice, Montecatini Terme

Duration11 days

From

USD 3,305

USD 3,206

Saving

USD 99

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European Trail - May 2027

(1 review )

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This tour was so much fun. Learnt a lot, met a lot of new friends, and had a ton of fun. Would highly recommend this tour, and to travel through Europe in general.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel, Hostel, Resort

Age Range

18-35 yrs

Operated in

english

Destinations

Paris, London, Amsterdam, Berlin

Paris, London, Amsterdam, Berlin, Prague, Vienna, Krakow, Budapest, Ljubljana, Venice, Rome, Florence, Swiss Alps

Duration23 days

From

USD 2,795

USD 2,711

Saving

USD 84

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14% OFF TODAY

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Rome and Tuscan Highlights - May 2027

4.8

(48 reviews )

No booking fees

Best price guaranteed

I chose this trip because of the 6 nights in Tuscany - Montecatini Terme. Cinque Terre, Lucca, Siena and San Gimignano were highlights of this tour. The food for the special dinners was amazing. Rosella and Massimo kept things on track. Organizing and coordinating tickets, transportation (2 ferries, train and bus) and firsthand knowledge of the areas visited was well exhibited by Rosella. The specialty tour guides were knowledgeable and added extra flair to the excursions. Enjoyed the trip immensely.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Montecatini, Florence, Vin

Rome, Montecatini, Florence, Vinci, San Gimignano

14% OFF TODAY

Duration9 days

From

USD 2,750

USD 2,357

Saving

USD 393

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Northern Italy Including Cinque Terre - May 2027

16% OFF TODAY

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Northern Italy Including Cinque Terre - May 2027

4.5

(98 reviews )

No booking fees

Best price guaranteed

Very enjoyable, with a variety of interesting locations.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Milan, Baveno, Italian Riviera

Milan, Baveno, Italian Riviera, Cinque Terre, Lake Maggiore

16% OFF TODAY

Duration8 days

From

USD 2,395

USD 2,021

Saving

USD 374

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15% OFF TODAY

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Best of Italy and Sicily - May 2027

4.7

(55 reviews )

No booking fees

Best price guaranteed

The Hotel were ok but did not cater to the tourist. The rooms did not have the use of the fans and found the air stagnant. A little air moving would helped. The Hotel in Sicily in Jiardini Naxos, Caeser palace, found the hotel desk determinitly unhelpful.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, Palermo, Assisi, L

Rome, Venice, Palermo, Assisi, La Spezia, Florence, Monreale, Agrigento, Taormina, Sorrento, Capri, Vatican City

15% OFF TODAY

Duration15 days

From

USD 5,225

USD 4,422

Saving

USD 803

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8% OFF TODAY

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Italian Escape and Sicily - May 2027

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Best price guaranteed

This one swings you from Rome to Naples, the home of pizza and gateway to Pompeii, before gliding along the dreamy Amalfi Coast. After falling for Capri and postcard pretty Positano, it's time to head to Sicily for a week of dreamy beaches, incredible food and endless ancient history. This Italian adventure has a little something for everyone.

Adventure

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

18-35 yrs

Operated in

english

Destinations

Rome, Sicily, Cefalu, Palermo, N

Rome, Sicily, Cefalu, Palermo, Naples, Amalfi Coast, Catania, Taormina, Syracuse

8% OFF TODAY

Duration13 days

From

USD 2,845

USD 2,629

Saving

USD 216

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Northern Italian Lakes & Countryside - May 2027

18% OFF TODAY

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Northern Italian Lakes & Countryside - May 2027

3.9

(48 reviews )

No booking fees

Best price guaranteed

This tour took us to some amazing destinations. Our tour director, and our bus operator were absolutely exceptional.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Milan, Baveno, Bergamo, Verona

Milan, Baveno, Bergamo, Verona, Mantua, Garda, Modena

18% OFF TODAY

Duration9 days

From

USD 2,725

USD 2,239

Saving

USD 486

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Real Sicily - May 2027

3.9

(7 reviews )

No booking fees

Best price guaranteed

Laid back, great people, awesome add ons, and great guide.

AdventureSightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

18-35 yrs

Operated in

english

Destinations

Catania, Sicily, Taormina, Syrac

Catania, Sicily, Taormina, Syracuse, Cefalu, Palermo

Duration8 days

From

USD 1,601

USD 1,553

Saving

USD 48

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Tuscan Escape - May 2027

(4 reviews )

No booking fees

Best price guaranteed

Great trip overall. The day trip were great. I wish the hotel was near a town or close to restaurants, but overall very great trip

Chill outLocal culture

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-35 yrs

Operated in

english

Destinations

Rome, Tuscany, Florence, Lucca

Rome, Tuscany, Florence, Lucca, Montalcino

Duration7 days

From

USD 1,325

USD 1,285

Saving

USD 40

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13% OFF TODAY

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Splendours of Italy - May 2027

(27 reviews )

No booking fees

Best price guaranteed

Very organized with a professional tour director and Driver!

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

13% OFF TODAY

Duration13 days

From

USD 2,725

USD 2,361

Saving

USD 364

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16% OFF TODAY

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Contrasts of Italy - May 2027

4.8

(37 reviews )

No booking fees

Best price guaranteed

The attention to the little details was so much appreciated! Amazing once in a lifetime experience!

Cruise

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, Florence

16% OFF TODAY

Duration10 days

From

USD 4,025

USD 3,365

Saving

USD 660

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15% OFF TODAY

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Great Italian Cities - May 2027

4.8

(158 reviews )

No booking fees

Best price guaranteed

It was a beautiful, historic overview of the heart of Italy. Our guide , was fantastic, caring and knowledgeable.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Munich, Venice, Florence

15% OFF TODAY

Duration10 days

From

USD 2,875

USD 2,449

Saving

USD 426

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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.

All Italy Tours in May 2027

Page 2 of 26 Trips in Italy during May 2027 with 1,509 Reviews

See Italy tours by duration

Italy Bellissimo - May 2027

European Trail - May 2027

Rome and Tuscan Highlights - May 2027

Northern Italy Including Cinque Terre - May 2027

Best of Italy and Sicily - May 2027

Italian Escape and Sicily - May 2027

Northern Italian Lakes & Countryside - May 2027

Real Sicily - May 2027

Tuscan Escape - May 2027

Splendours of Italy - May 2027

Contrasts of Italy - May 2027

Great Italian Cities - May 2027

Page 2 of 26 Trips in Italy during May 2027 with 1,509 Reviews

Combine Italy in May with Nearby Countries for an Unforgettable Trip

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 Italy Tours in May 2027

Page 2 of 26 Trips in Italy during May 2027 with 1,509 Reviews

See Italy tours by duration

Page 2 of 26 Trips in Italy during May 2027 with 1,509 Reviews