10 Best Italy Multiday Tours in May 2027

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Best of Italy - May 2027

4.8

(171 reviews )

No booking fees

Best price guaranteed

Our guide was very professional and knowledgeable which helped a great deal. It got us to places we never would have gone to by ourselves .

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome

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Duration11 days

From

USD 5,795

USD 5,514

Saving

USD 281

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14% OFF TODAY

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Italian Concerto - May 2027

4.7

(123 reviews )

No booking fees

Best price guaranteed

Great tour at a great price

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, Amalfi Coast & Cam

Rome, Venice, Amalfi Coast & Campania, Capri, Florence

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Duration11 days

From

USD 3,925

USD 3,374

Saving

USD 551

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Southern Italy and Sicily - May 2027

4.4

(104 reviews )

No booking fees

Best price guaranteed

All the options were excellent. The local guides walked at a slow pace giving us time to take pictures. Our guide Alfonso and our driver Tito were great. We would take a tour with them anytime

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Pompeii, Rome, Sorrento, Palermo

Pompeii, Rome, Sorrento, Palermo, Capri, Taormina, Agrigento

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Duration10 days

From

USD 3,575

USD 3,051

Saving

USD 524

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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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Grand Italy & Sicily - May 2027

4.7

(77 reviews )

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It covers so many areas in Italy We got exposed to so much history and culture

Wine tasting tours

Tour Type

Group Tour

Accommodation

Hotel, Resort, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Palermo, Sorrento, Capri

Rome, Palermo, Sorrento, Capri, Alberobello, Giardini Naxos, Santa Margherita, Portofino, Lake Maggiore, Venice, Florence

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Duration17 days

From

USD 8,250

USD 6,993

Saving

USD 1,257

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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

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Duration9 days

From

USD 2,750

USD 2,357

Saving

USD 393

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Northern Italy Including Cinque Terre - May 2027

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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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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

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Duration15 days

From

USD 5,225

USD 4,422

Saving

USD 803

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Country Roads Of Tuscany & Central Italy - May 2027

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Country Roads of Tuscany & Central Italy - May 2027

4.9

(24 reviews )

No booking fees

Best price guaranteed

Great way to see the true Italy

Museum and gallery visits

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice

6% OFF TODAY

Duration9 days

From

USD 4,025

USD 3,768

Saving

USD 257

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Shrines of Italy - May 2027

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From the hallowed Basilica of St. Francis to the glorious Sistine Chapel, discover why Italy is a bastion of Catholicism. Spend time at the Basilica of St. Francis in Assisi, the beloved saint’s hometown. Stay two nights in San Giovanni Rotondo. Reflect at the Grotto of Michael the Archangel. Discover the cathedral of Salerno and the abbey of Montecassino. Explore the burial sites of the Catacombs where the early Christians hid and venerated their dead. Attend the weekly Papal audience and receive the blessing given by the Holy Father. Discover Michelangelo’s Last Judgment mural and explore St. Peter’s Basilica. See the world’s most inspirational sites and relics on a journey through the rolling hills and lively cities of Italy.

Art and architecture

Tour Type

Group Tour

Accommodation

Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Rome, Assisi, San Giovanni Roton

Rome, Assisi, San Giovanni Rotondo, Amalfi Coast & Campania

Duration11 days

From

USD 2,849

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Reflections of Italy - May 2027

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Best price guaranteed

Embark on a captivating journey that takes you from the piazzas of Rome to the canals of Venice. Discover the rolling hills of the scenic Tuscan and Umbrian countryside. Explore medieval hill towns and visit Assisi, the birthplace of St. Francis. Spend time at a historic winery in the heart of the Chianti region and enjoy a chef-led cooking class with lunch. Discover the masterpieces of the Renaissance in Florence. See glass transformed into exquisite art on Murano Island. Linger in iconic Venice for 2 nights. Journey to the shores of glamorous Lake Como. Encounter a land rich in history, culture, art, and romance.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Milan, Rome, Lake Como, Perugia

Milan, Rome, Lake Como, Perugia, Florence, Venice

Duration10 days

From

USD 2,949

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Northern Italian Lakes & Countryside - May 2027

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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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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 34 Trips in Italy during May 2027 with 1,597 Reviews

See Italy tours by duration

Best of Italy - May 2027

Italian Concerto - May 2027

Southern Italy and Sicily - May 2027

Italy Bellissimo - May 2027

European Trail - May 2027

Grand Italy & Sicily - May 2027

Rome and Tuscan Highlights - May 2027

Northern Italy Including Cinque Terre - May 2027

Best of Italy and Sicily - May 2027

Country Roads of Tuscany & Central Italy - May 2027

Shrines of Italy - May 2027

Reflections of Italy - May 2027

Northern Italian Lakes & Countryside - May 2027

Real Sicily - May 2027

Page 2 of 34 Trips in Italy during May 2027 with 1,597 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 34 Trips in Italy during May 2027 with 1,597 Reviews

See Italy tours by duration

Page 2 of 34 Trips in Italy during May 2027 with 1,597 Reviews