10 Best Italy Multiday Tours in May 2027

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Great Italian Cities - May 2027

4.8

(162 reviews )

No booking fees

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It was a beautiful, historic overview of the heart of Italy. Our guide , was fantastic, caring and knowledgeable.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Munich, Venice, Florence

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Duration10 days

From

USD 2,875

USD 2,449

Saving

USD 426

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Rome by golf-cart private tour - May 2027

(4 reviews )

No booking fees

Best price guaranteed

We had a 7 hour private golf cart tour with Eduardo. He took us to see all the sites that we wanted to see. He brought us to unique places we would never of known about. Eduardo was so personable and knowledgeable . I highly recommend this tour!!

Sightseeing Tours

Tour Type

Private Tour

Age Range

1-99 yrs

Operated in

english, german, dutch, italian, spanish

Destinations

Rome

Duration3 hours

From

USD 117

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

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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

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Duration11 days

From

USD 4,999

USD 4,649

Saving

USD 350

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Sicily and Its Isles - May 2027

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Explore Sicily – an island paradise nestled amongst the deep blue waves of the Mediterranean. Sample specialties in Palermo’s colorful food market. Taste organic olive oil and learn how sustainable production methods support opposing the Mafia. Explore Agrigento’s Valley of the Temples (UNESCO) with a guide. Enjoy two nights on the Isle of Salina and visit a traditional caper farm. Spend two nights in Taormina, perched above the Ionian Sea. See Mount Etna from a different perspective on an off-road excursion. Discover how ancient traditions blend into modern society as you travel along Sicily and two of its beloved isles.

Country side and village visits

Tour Type

Group Tour

Accommodation

Resort, Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Palermo, St Julian's, Cefalu, Sa

Palermo, St Julian's, Cefalu, Salinà, Taormina, Marsala, Agrigento

Duration14 days

From

USD 4,899

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Venice and Croatian Islands Cruise - May 2027

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Explore the Slovenian coastline, admire Croatia’s trendiest islands along the northern Adriatic Sea from a privately chartered ship and discover magical Venice. Sail around Kornati National Park – known as Croatia’s “nautical paradise” – and disembark on the largest island, Krk and then the colorful island of Cres. Get ready for more than just beautiful scenery as you experience traditional Dalmatian delicacies, savor the sweet flavor of Rab cake, and an afternoon lunch at a family-owned winery in the Collio region. Uncover the hidden beauty and wondrous history of this Mediterranean gem.

National parksCruise

Tour Type

Group Tour

Accommodation

Resort, Ship Cabin, Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Sibenik, Venice, Zagreb, Split

Sibenik, Venice, Zagreb, Split, Portoroz, Murano Island, Telascica, Zadar, Rab, Krk, Cres, Opatija

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Duration13 days

From

USD 4,999

USD 4,749

Saving

USD 250

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Walks & Food of the Italian Riviera - May 2027

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The Italian Riviera still has secrets to share… if you know where to go. One of them is seaside Chiavari, ideally placed between Genoa and the Cinque Terre. From this base, we embark on a well-balanced blend of scenic walks, cultural landmarks and exquisite regional cuisine. You’ll sip wine with world-renowned producers, master pasta and pesto with professional chefs, and hike glorious trails. A free day to visit the Cinque Terre will be a must for most, while the pleasure of staying away from the tourists allows you to enjoy the Italian Riviera in peace.

Trekking and Hiking

Tour Type

Small Group Tour

Accommodation

Hotel, Resort

Age Range

16-99 yrs

Operated in

english

Destinations

Genoa, Chiavari, Cinque Terre, Palmaria

Duration7 days

From

USD 3,600

USD 3,492

Saving

USD 108

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Journeys: Northern Italy, Venice to Florence - May 2027

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Connect with stunning landscapes, rich Italian heritage and delicious food on this 7-day journey through northern Italy. Experience the iconic canals and historic architecture of Venice and soak in the picturesque beauty of the coastal villages of Cinque Terre on the Italian Riviera. Visit the birthplace of the Renaissance–Florence, a city steeped in art and art history.

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

12-100 yrs

Operated in

english

Destinations

Florence, Venice, Cinque Terre

Duration7 days

From

USD 2,999

USD 2,909

Saving

USD 90

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Journeys: Southern Italy, Naples to Rome - May 2027

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Bask in the natural beauty and in the incredible food of southern Italy on this 8-day explorative journey from Naples to Rome. Walk in ancient footsteps alongside an archaeologist through Pompeii, a city preserved for centuries by ash and volcanic debris. Follow trails with spectacular views along the Amalfi Coast. Take a foodie walk in Naples and visit a lemon farm in Sorrento before heading to Rome, Italy’s capital to soak in the culture, history and iconic monuments.

Explorer

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

12-100 yrs

Operated in

english

Destinations

Rome, Naples, Sorrento, Amalfi Coast

Duration8 days

From

USD 3,399

USD 3,297

Saving

USD 102

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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 5 of 64 Trips in Italy during May 2027 with 3,126 Reviews

See Italy tours by duration

Great Italian Cities - May 2027

Rome by golf-cart private tour - May 2027

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

Sicily and Its Isles - May 2027

Venice and Croatian Islands Cruise - May 2027

Walks & Food of the Italian Riviera - May 2027

Journeys: Northern Italy, Venice to Florence - May 2027

Journeys: Southern Italy, Naples to Rome - May 2027

Page 5 of 64 Trips in Italy during May 2027 with 3,126 Reviews

Combine Italy in May with Nearby Countries for an Unforgettable Trip

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Food, wine, events and nightlife

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Wildlife, landscapes and nature

Boat tours, water sports and marine wildlife

Sightseeing, attractions, culture and history

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Beach, romance, getaways and relaxation

Special interests and hobbies

All Italy Tours in May 2027

Page 5 of 64 Trips in Italy during May 2027 with 3,126 Reviews

See Italy tours by duration

Page 5 of 64 Trips in Italy during May 2027 with 3,126 Reviews