10 Best Italy Multiday Tours in May 2027

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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Cycling in Sicily - May 2027

4.7

(58 reviews )

No booking fees

Best price guaranteed

This was one of my best Exodus Holidays. This was my first cycling one with Exodus and I can highly recommend this trip.

Bicycle tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Syracuse, Modica, Marzamemi, Noto

Duration8 days

From

USD 2,700

USD 2,619

Saving

USD 81

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16% OFF TODAY

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Grand Italian Experience - May 2027

4.8

(74 reviews )

No booking fees

Best price guaranteed

So much to do! Don't muss out on the additional dinners. Some are spectacular.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Dolomites, Lake Maggiore

Rome, Dolomites, Lake Maggiore, Viareggio, Florence, Puglia, Amalfi Coast & Campania, Naples, Assisi, Venice

16% OFF TODAY

Duration17 days

From

USD 5,750

USD 4,802

Saving

USD 949

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7% OFF TODAY

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Easy Pace Italy - May 2027

4.8

(113 reviews )

No booking fees

Best price guaranteed

Good introductory cross-section in major cities. Good balance of scheduled vs. free time. Would like a little more emphasis on art--especially Uffizi Gallery and Pisan Camposanto--plus entry into St. Mark's/Doge's Palace and Duomo church (rather than some of the shopping stuff). A little too much commercial, too little history/art. (Some of guides under-informed, including one who said Galileo discovered the "two planets" around Jupiter!).

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, Florence

7% OFF TODAY

Duration10 days

From

USD 5,175

USD 4,835

Saving

USD 340

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8% OFF TODAY

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Simply Italy - May 2027

No booking fees

Best price guaranteed

Welcome to 15 days of pure Italian travel immersion. Covering Rome, Florence, Venice and beyond, this one brings you the blissful best of this soul-stirring country. Explore Rome's historical highlights, travel through the streets of Michelangelo's Florence, indulge in some authentic pasta on the Amalfi Coast. Stop by to see the stooping slopes of Sorrento in the breezy winter. And that's just an aperitivo. Beauty, romance and all the pasta you can fit in; the good life just got even better. That's amore!

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

18-35 yrs

Operated in

english

Destinations

Rome, Naples, Amalfi Coast, Flor

Rome, Naples, Amalfi Coast, Florence, Cinque Terre, Milan, Venice

8% OFF TODAY

Duration15 days

From

USD 2,755

USD 2,538

Saving

USD 217

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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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8% OFF TODAY

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Italian Espresso - May 2027

No booking fees

Best price guaranteed

10 days of la dolce vita, pronto. This one is pure Italian travel, covering all the big bucket-list destinations of Venice, Florence & Rome, plus the smaller charms of Pisa, Verona, and Siena. We'll ooh and aah over antipasto & chianti, dine on regional specialities in local trattorias, boat through the canals and islands of Venice, and explore the architecturally magnificent city of Florence. Expect plenty of world-famous espresso & pizza on the way.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

18-35 yrs

Operated in

english

Destinations

Rome, Venice, Florence, Cinque T

Rome, Venice, Florence, Cinque Terre, Milan

8% OFF TODAY

Duration10 days

From

USD 2,035

USD 1,875

Saving

USD 160

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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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8% OFF TODAY

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Italian Escape - May 2027

No booking fees

Best price guaranteed

This all-Italian adventure kicks off in the historic heart of Rome, then heads to Naples—the birthplace of pizza. You'll explore the perfectly preserved ruins of Pompeii before soaking up the sun and sipping limoncello along the stunning Amalfi Coast (with a stop in postcard-perfect Sorrento, of course). By the end of this unforgettable 6-day Italian escape, you'll have a belly full of pizza, a camera full of memories, and a serious craving to come back for more.

Food tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

18-35 yrs

Operated in

english

Destinations

Rome, Pisa

8% OFF TODAY

Duration6 days

From

USD 1,331

USD 1,227

Saving

USD 104

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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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8% OFF TODAY

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Ultimate Italy - May 2027

(1 review )

No booking fees

Best price guaranteed

I met some amazing people and saw so many incredible sights in Italy! This trip exceeded my expectations!

Chill outAdventure

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

18-35 yrs

Operated in

english

Destinations

Rome, Venice, Naples, Amalfi, Ca

Rome, Venice, Naples, Amalfi, Catania, Taormina, Syracuse, Cefalu, Florence, Palermo, Cinque Terre, Milan

8% OFF TODAY

Duration22 days

From

USD 4,485

USD 4,140

Saving

USD 345

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15% OFF TODAY

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Colours of Sicily - May 2027

4.7

(91 reviews )

No booking fees

Best price guaranteed

Your tour involves an intimate weaving of the Sicilian people and their lives and customs. We saw church celebrations ate special foods, saw volcanic activity, toured organic farms and gardens and much more!

MountainsLocal culture

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Palermo, Catania, Marsala, Sicil

Palermo, Catania, Marsala, Sicily, Ragusa, Syracuse, Taormina

15% OFF TODAY

Duration9 days

From

USD 2,275

USD 1,925

Saving

USD 350

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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

View Tours

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

See Italy tours by duration

Private Gourmet Wine Tour in Tuscany - May 2027

Cycling in Sicily - May 2027

Grand Italian Experience - May 2027

Easy Pace Italy - May 2027

Simply Italy - May 2027

Ultimate Italy - May 2027

Italian Espresso - May 2027

Sicily Grand Tour - May 2027

Italian Escape - May 2027

Journeys: Iconic Italy - May 2027

Wonders of Italy - May 2027

Italian Escapade - May 2027

Ultimate Italy - May 2027

Colours of Sicily - May 2027

Page 2 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 2 of 99 Trips in Italy during May 2027 with 3,171 Reviews

See Italy tours by duration

Page 2 of 99 Trips in Italy during May 2027 with 3,171 Reviews