10 Best Italy Multiday Tours in May 2027

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Sicily Grand Tour - May 2027

4.4

(12 reviews )

No booking fees

Best price guaranteed

The 15 day tour of Sicily was absolutely fantastic. The best tour guide ever, her name is Milena. A wonderful driver Alessandro. I felt that it was a pretty comprehensive tour of Sicily seeing all the highlights plus more. Fabulous food in restaurants where we ere taken by Milena. Verdict EXCELLENT.

Local culture

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

16-99 yrs

Operated in

english

Destinations

Catania, Taormina, Palermo, Cefa

Catania, Taormina, Palermo, Cefalu, Mount Etna, Syracuse, Sicily, Modica, Piazza Armerina, Trapani

Duration15 days

From

USD 4,800

USD 4,656

Saving

USD 144

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Journeys: Iconic Italy - May 2027

(4 reviews )

No booking fees

Best price guaranteed

Overall the trip was extremely enjoyable and I will cherish my memories of the incredible towns and sites that we visited.

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

12-100 yrs

Operated in

english

Destinations

Rome, Venice, Amalfi, Cinque Ter

Rome, Venice, Amalfi, Cinque Terre, Florence, Naples, Sorrento

Duration14 days

From

USD 6,499

USD 6,304

Saving

USD 195

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15% OFF TODAY

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Wonders of Italy - May 2027

4.7

(95 reviews )

No booking fees

Best price guaranteed

Very laid back and easy with two days in most places and a good quantity of free time. Fantastic tour director who kept her flock in control. Driver was phenomenal and a pleasure to talk to. As always there is too much to see and remember so picture taking is essential.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Lucca, Florence, Venice, Assisi

15% OFF TODAY

Duration11 days

From

USD 3,075

USD 2,606

Saving

USD 469

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6% OFF TODAY

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Italian Escapade - May 2027

4.8

(76 reviews )

No booking fees

Best price guaranteed

It was a very busy itinerary but in knew it would be in order to see so many wonderful sites in Italy! Fantastic trip!

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Sorrento, Capri, Florence

Rome, Sorrento, Capri, Florence, Lake Maggiore, Venice, Assisi

6% OFF TODAY

Duration13 days

From

USD 6,795

USD 6,407

Saving

USD 388

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7% OFF TODAY

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Italian Elegance - May 2027

4.8

(30 reviews )

No booking fees

Best price guaranteed

The guides are the best and make all the difference.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, Florence, San Gimi

Rome, Venice, Florence, San Gimignano, Santa Margherita, Cinque Terre, Lake Maggiore, Cortina d'Ampezzo

7% OFF TODAY

Duration12 days

From

USD 6,025

USD 5,602

Saving

USD 423

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5% OFF TODAY

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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

5% OFF TODAY

Duration11 days

From

USD 5,795

USD 5,514

Saving

USD 281

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16% OFF TODAY

Super Sales

Country Roads of Italy - May 2027

4.6

(65 reviews )

No booking fees

Best price guaranteed

This tour was a wonderful experience. A nice size at 28 happy people, luxurious coach, amazing driver & guide extraordinaire . Accommodations were very good & often pleasantly out of the ordinary. The optional activities are worth the extra expense. Highly recommend this tour.

Countryside and village visits

Tour Type

Group Tour

Accommodation

Hotel, Resort, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, Monteriggioni, Luc

Rome, Venice, Monteriggioni, Lucca, Sorrento, Todi

16% OFF TODAY

Duration16 days

From

USD 7,895

USD 6,665

Saving

USD 1,230

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15% OFF TODAY

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Italian Glory - May 2027

4.8

(55 reviews )

No booking fees

Best price guaranteed

Great itinerary and tour director. Suggest: a slightly slower pace - limiting yourself to 1 optional experience/ day to avoid too/ long days -exhaustion, provide more suggestions for authentic food / restaurants on ‘free’ days.

Chill outSightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Milan, Rome, Lake Como, Como, Ve

Milan, Rome, Lake Como, Como, Venice, Florence, Amalfi Coast & Campania

15% OFF TODAY

Duration13 days

From

USD 4,575

USD 3,880

Saving

USD 695

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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

14% OFF TODAY

Duration11 days

From

USD 3,925

USD 3,374

Saving

USD 551

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Self-Guided Culinary Package - La Spezia & Cinque Terre - May 2027

Trip customizable

Best price guaranteed

Join us on this three-day tour and get to enjoy a region of Italy known for its mild climate, charming port towns, breath-taking landscapes, and fresh local cuisine. Liguria is home to the UNESCO World Heritage site "Cinque Terre," a majestic and astonishing national park free of vehicular traffic and perfect for romantic getaways and fine culinary experiences. The regional cuisine of Liguria is based on seafood, fresh vegetables and herbs, such as in the famous pesto alla Genovese. In a span of few days, you will be able to explore this region, its history, culture and culinary highlights always taking your time and doing everything at your own pace.

Food tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

9-79 yrs

Operated in

English

Destinations

Cinque Terre and Liguria, Liguri

Cinque Terre and Liguria, Liguria, Cinque Terre, La Spezia, Lerici

Duration3 days

From

USD 387

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15% OFF TODAY

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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

15% OFF TODAY

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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Super Sales

European Trail - May 2027

(1 review )

No booking fees

Best price guaranteed

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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The Heart of the Cilento National Park - May 2027

(2 reviews )

Trip customizable

Best price guaranteed

Thank you so much for making this a GREAT vacation.

Trekking and Hiking

Tour Type

Private Tour

Age Range

18-99 yrs

Operated in

English

Destinations

Amalfi Coast & Campania, Paestum

Amalfi Coast & Campania, Paestum, Valle Dell'Angelo, Roscigno, Sant'Angelo A Fasanella

Duration9 days

From

USD 809

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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 47 Trips in Italy during May 2027 with 2,080 Reviews

See Italy tours by duration

Sicily Grand Tour - May 2027

Journeys: Iconic Italy - May 2027

Wonders of Italy - May 2027

Italian Escapade - May 2027

Italian Elegance - May 2027

Best of Italy - May 2027

Country Roads of Italy - May 2027

Italian Glory - May 2027

Italian Concerto - May 2027

Self-Guided Culinary Package - La Spezia & Cinque Terre - May 2027

Southern Italy and Sicily - May 2027

Italy Bellissimo - May 2027

European Trail - May 2027

The Heart of the Cilento National Park - May 2027

Page 2 of 47 Trips in Italy during May 2027 with 2,080 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 47 Trips in Italy during May 2027 with 2,080 Reviews

See Italy tours by duration

Page 2 of 47 Trips in Italy during May 2027 with 2,080 Reviews