10 Best Italy Multiday Tours in May 2027

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Italian Holiday - May 2027

4.8

(154 reviews )

No booking fees

Best price guaranteed

Very well organized from beginning to end

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, The Vatican, Venice, Veron

Rome, The Vatican, Venice, Verona, Florence

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Duration7 days

From

USD 2,125

USD 1,811

Saving

USD 314

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Private Tour of Sicily from Palermo - May 2027

4.8

(4 reviews )

Trip customizable

Best price guaranteed

This is our first private tour and I must say it met all our expectations. Our driver/guide Carlo took very good care of us, told us informative and amusing stories along the way and took us to wonderful restaurants. He made sure all our needs our taken cared of. In Sicily especially I think the private tour is a big advantage as there are many places where only small vehicles can go through. We made the right decision in choosing this tour.

City sightseeing

Tour Type

Private Tour

Accommodation

Hotel, Villa

Age Range

20-99 yrs

Operated in

english

Destinations

Palermo, Catania, Taormina, Sici

Palermo, Catania, Taormina, Sicily, Agrigento, Marsala, Monreale

Duration8 days

From

USD 3,150

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Treasures of Italy - May 2027

4.8

(88 reviews )

No booking fees

Best price guaranteed

It was a fast paced trip. It is a bit difficult staying only one night in a few places, just the logistics of packing up several nights and having everything ready for the next day is challenging. But, that being said I thoroughly enjoyed seeing so many things through out Italy. That inconvenience was minor in comparison to the amount of ground we covered.

Museum and gallery visits

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice

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Duration11 days

From

USD 5,125

USD 4,894

Saving

USD 231

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Private Gourmet Wine Tour in Tuscany - May 2027

4.5

(2 reviews )

Trip customizable

Best price guaranteed

What a beautiful time spent in Tuscany on this trip. This was a wonderful tour. Great accommodations! Fabulous wines and meals. We had a wonderful driver, Brando, who was patient and knowledgeable. This is a trip well worth it. Villa Lecchi was elegant and made us feel very special! Spectacular location in the heart of Chianti hills

Food toursWine tasting tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

22-89 yrs

Operated in

english, german

Destinations

Tuscany, Chianti, Florence, Sien

Tuscany, Chianti, Florence, Siena, Pisa

Duration4 days

From

USD 2,845

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Ultimate Italy - May 2027

(30 reviews )

No booking fees

Best price guaranteed

It was a great experience with many highlights throughout our tour. We particularly enjoyed the many immersive stops (i.e. wine tasting, weaving, truffle hunting, pasta making, etc.) in addition to our guided tours. Our tour guide, was very well versed, knowledgeable, and helpful and provided good insights and tips throughout our trip. I can't imagine someone else doing a better job than she did! The local experts were also on top of their games.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel, Lodge, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, Capri, Perugia, Sa

Rome, Venice, Capri, Perugia, San Gimignano, Florence, Rapallo

Duration12 days

From

USD 10,850

USD 10,525

Saving

USD 326

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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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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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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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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

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Duration8 days

From

USD 2,395

USD 2,021

Saving

USD 374

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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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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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Discover Castel del Monte (UNESCO) - 2 Hour Guided Tour - May 2027

Trip customizable

Best price guaranteed

In the heart of Puglia is hidden the most important monument of the Middle Ages in Italy, a treasure of beauty and mystery to explore. Castel del Monte was built on top of a hill where you can see a good part of the Puglia Region and the cities of the coast with a beautiful landscape. Castel del Monte is certainly the most important building that has left the Emperor Frederick II Hohenstaufen of Swabia, full of mysteries not fully revealed. At the base of its construction there is always the number 8. After many years of neglect, during which the castle was stripped of furniture and decorations of marble, has become a refuge for shepherds, brigands and political refugees. In 1876 the castle was bought and restored by the Italian state. In 1996 it was declared a UNESCO World Heritage for the perfection of its shape and the harmonious union of cultural elements from northern Europe, the Islamic world and classical antiquity and because it represented the personality of its creator Frederick II Hohenstaufen. The tour you will discover the exteriors and interiors of the 'castle' and describe the secrets of the historical context in which it was built.

Cultural, religious and historic sites

Tour Type

Group Tour

Age Range

5-79 yrs

Operated in

english, german, italian

Destinations

Andria

Duration2 hours

From

USD 129

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Alpine Lakes & Scenic Trains featuring a cruise on Lake Maggiore and scenic trains in Switzerland & Italy - May 2027

No booking fees

Best price guaranteed

Climb aboard legendary Alpine railways and set out on a journey across the captivating Alpine landscapes of Switzerland and Italy. Ride two legendary train routes – the Glacier Express and the Bernina Pass Train. Relax in some of Europe’s most stunning and exclusive resort villages, including Zermatt, St. Moritz and Lake Maggiore, Italy. Explore Lucerne, the "Swiss Paradise on the Lake.” Ascend Pilatus on a unique excursion along the steepest railway in the world, soaking in the scenery from 7,000 feet above sea level. These are the Alpine views you’ve been dreaming of.

Natural landmarks sightseeing

Tour Type

Group Tour

Accommodation

Resort, Hotel, Villa, Ship Cabin

Age Range

1-99 yrs

Operated in

english

Destinations

Lombardy & the Lakes, Lucerne, L

Lombardy & the Lakes, Lucerne, Lake Maggiore, Zurich, Zermatt, St. Moritz

Duration11 days

From

USD 4,999

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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

14 Trips in Italy during May 2027 with 674 Reviews

See Italy tours by duration

Italian Holiday - May 2027

Private Tour of Sicily from Palermo - May 2027

Treasures of Italy - May 2027

Private Gourmet Wine Tour in Tuscany - May 2027

Ultimate Italy - May 2027

Italy Bellissimo - May 2027

European Trail - May 2027

The Heart of the Cilento National Park - May 2027

Italian Vistas - May 2027

Northern Italy Including Cinque Terre - May 2027

Northern Italian Lakes & Countryside - May 2027

Splendours of Italy - May 2027

Discover Castel del Monte (UNESCO) - 2 Hour Guided Tour - May 2027

Alpine Lakes & Scenic Trains featuring a cruise on Lake Maggiore and scenic trains in Switzerland & Italy - May 2027

14 Trips in Italy during May 2027 with 674 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

14 Trips in Italy during May 2027 with 674 Reviews

See Italy tours by duration

14 Trips in Italy during May 2027 with 674 Reviews