10 Best Italy Multiday Tours in May 2027

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

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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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Classic Dolomites Hikes - Premium Adventure - May 2027

4.9

(24 reviews )

No booking fees

Best price guaranteed

What a wonderful trip ! An exciting walking adventure with a wonderful guide, magnificent scenery , a great group of likeminded hikers and an awesome hotel

Trekking and Hiking

Tour Type

Small Group Tour

Accommodation

Hotel, Hut

Age Range

16-99 yrs

Operated in

english

Destinations

Niederdorf, Dolomites, Lago Di B

Niederdorf, Dolomites, Lago Di Braies, Alpe Nemes, Strudelkopf, Brunico, Tre Cime Di Lavaredo, Monte Piano

Duration8 days

From

USD 3,420

USD 3,317

Saving

USD 103

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16% OFF TODAY

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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

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Duration16 days

From

USD 7,895

USD 6,665

Saving

USD 1,230

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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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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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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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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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Grand Italy & Sicily - May 2027

4.7

(77 reviews )

No booking fees

Best price guaranteed

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

15% OFF TODAY

Duration17 days

From

USD 8,250

USD 6,993

Saving

USD 1,257

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Country Roads Of Northern Italy - May 2027

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Country Roads of Northern Italy - May 2027

4.5

(48 reviews )

No booking fees

Best price guaranteed

Keep the flexibility of the add on activities.

AdventureCity sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Milan, Trento, Lake Maggiore

14% OFF TODAY

Duration10 days

From

USD 4,450

USD 3,841

Saving

USD 609

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Highlights of Matera and Apulia Private Tour - May 2027

(1 review )

Trip customizable

Best price guaranteed

Private Tour around Apulia and Matera beyond our expectations .Very good the Hotel in Matera, Dimora di Metello..but also Tenuta Monacelle near Alberobello. Great local guide and meals. I only think you should had add an extra day in Apulia, 5 days are not enough. Anyway excellent tour and service. Very good value for money

Sightseeing ToursFood tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

20-99 yrs

Operated in

english

Destinations

Matera, Puglia, Polignano A Mare

Matera, Puglia, Polignano A Mare, Alberobello, Monopoli, Bari

Duration5 days

From

USD 2,310

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Italian Vistas - May 2027

No booking fees

Best price guaranteed

From the ancient ruins of Pompeii to the chic charm of the Sorrento Coast, embark on a spectacular Italian getaway. Enjoy multiple-night stays in Rome, the charming coastal town of Sorrento, Florence, Venice, and Stresa in the Lake District. Discover the treasures of Classical Rome, including the Colosseum. Walk in the footsteps of the ancient Romans in Pompeii. Take a boat to the enchanting Isle of Capri. See the gems of the Renaissance in Florence, a veritable open-air museum. Marvel at the Leaning Tower of Pisa and stroll the streets of Verona. Stop at a Tuscan winery and farm for a lunch of regional specialties and wines. Tour Venice and walk the Castello district. Cruise to Isola dei Pescatori, one of the scenic Borromean Islands. Delve deeper into its history and culture as you visit some of the world’s most beautiful locales.

Natural landmarks sightseeing

Tour Type

Group Tour

Accommodation

Resort, Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Rome, Lombardy & the Lakes, Veni

Rome, Lombardy & the Lakes, Venice, Stresa, Sorrento, Florence

Duration13 days

From

USD 4,499

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Italy: Amalfi Coast to Puglia - May 2027

No booking fees

Best price guaranteed

Stray off the beaten path and explore a new side to the Italy you know and love. Sample wines created from the rich volcanic soil just outside of Pompeii. Soak up the sun with a free afternoon in Positano, home to colorful hillside houses and local posh boutiques. Spend 2 nights in a unique cave dwelling in Matera and your last 2 nights in the Puglia region in a personal converted trullo house. Uncover the Baroque excellence of Lecce, an artisan city of limestone. Make your way through southern Italy and experience the Amalfi Coast and the Puglia region.

Beach

Tour Type

Group Tour

Accommodation

Resort, Villa, Hotel, Hut

Age Range

1-99 yrs

Operated in

english

Destinations

Bari, Naples, Alberobello, Monop

Bari, Naples, Alberobello, Monopoli, Lecce, Minori, Matera

Duration14 days

From

USD 4,699

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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 3 of 99 Trips in Italy during May 2027 with 3,171 Reviews

See Italy tours by duration

Italian Elegance - May 2027

Best of Italy - May 2027

Classic Dolomites Hikes - Premium Adventure - May 2027

Country Roads of Italy - May 2027

Italian Glory - 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

Country Roads of Northern Italy - May 2027

Highlights of Matera and Apulia Private Tour - May 2027

Italian Vistas - May 2027

Italy: Amalfi Coast to Puglia - May 2027

Page 3 of 99 Trips in Italy during May 2027 with 3,171 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 3 of 99 Trips in Italy during May 2027 with 3,171 Reviews

See Italy tours by duration

Page 3 of 99 Trips in Italy during May 2027 with 3,171 Reviews