10 Best Italy Multiday Tours in May 2027

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Walking The Amalfi Coast - Summer Edition - May 2027

4.5

(2 reviews )

No booking fees

Best price guaranteed

The trip was fabulous -beautiful places , lovely hotel and friendly warm staff , excellent food wine and our leader Veriano was so kind engaging fun and made the trip even more enjoyable and our group was fabulous. Would go back tomorrow! Highly recommend it!

Trekking and HikingBeach

Tour Type

Small Group Tour

Accommodation

Hotel, Hut, Villa

Age Range

16-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Bomeran

Amalfi Coast & Campania, Bomerano, Atrani, Sorrento, Mount Vesuvius, Conca Dei Marini, Naples, Amalfi

Duration8 days

From

USD 2,175

USD 2,110

Saving

USD 65

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Southern Italy & Sicily featuring Taormina, Matera and the Amalfi Coast - May 2027

No booking fees

Best price guaranteed

Journey through a crossroads of civilizations in Sicily and on to the spectacular coastlines of Southern Italy. Uncover Sicily’s capital Palermo and its Moorish and Norman influences. Explore Agrigento’s ancient Valley of the Temples and the Ancient Roman mosaics of Piazza Armerina. Travel to the historic hilltop town of Taormina. Visit a local winery for a wine tasting and agriturismo dinner. Venture to the ancient cave dwellings of Sassi di Matera. Explore Sorrento and stunning Positano, the pearl of the Amalfi Coast. Walk in the footsteps of ancient Romans in the excavated Pompeii. Allow the unique culture to capture your heart and get a glimpse into an age-old heritage composed of ancient monuments and cultivated lands.

City sightseeing

Tour Type

Group Tour

Accommodation

Villa, Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Rome, Sorrento, Palermo, Sicily

Rome, Sorrento, Palermo, Sicily, Agrigento, Giardini Naxos, Matera

Duration13 days

From

USD 3,949

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Spotlight on Northern Italy featuring Venice, Verona & the Dolomites - May 2027

No booking fees

Best price guaranteed

Unpack once and take in the vineyards, villas, peaks, and prosecco of Veneto. Settle into a centrally located hotel in Treviso, the historic mainland outpost for the island-city of Venice. Savor the Venetian inspiration on terrafirma, solid ground, so you have the flexibility to explore on land and by water, with time to dive into Venice, Verona, and the Dolomites. Take in the artist haven of Asolo and get a taste of Italy’s Prosecco region. Immerse yourself in local culture at a historic villa near Bassano del Grappa, retracing the history of a noble family of Venice. This is your opportunity to dive in and truly experience Northern Italy.

City sightseeingLocal culture

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

1-99 yrs

Operated in

english

Destinations

Treviso, Verona, Venice, Asolo

Treviso, Verona, Venice, Asolo, Bassano Del Grappa

Duration9 days

From

USD 2,549

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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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16% OFF TODAY

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Contrasts of Italy - May 2027

4.8

(37 reviews )

No booking fees

Best price guaranteed

The attention to the little details was so much appreciated! Amazing once in a lifetime experience!

Cruise

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, Florence

16% OFF TODAY

Duration10 days

From

USD 4,025

USD 3,365

Saving

USD 660

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Country Roads Of Italy, A Women-only Tour - May 2027

15% OFF TODAY

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Country Roads of Italy, a Women-Only Tour - May 2027

4.7

(3 reviews )

No booking fees

Best price guaranteed

It was great traveling with other women. I felt some days were too busy, especially the miles we went one day for 45 minutes at a spare. Really enjoyed the meals.

Adventure

Tour Type

Group Tour

Accommodation

Hotel, Villa, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, San Gimignano, Luc

Rome, Venice, San Gimignano, Lucca, Parma, Sorrento, Todi, Perugia, Florence

15% OFF TODAY

Duration16 days

From

USD 7,475

USD 6,342

Saving

USD 1,133

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15% OFF TODAY

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Great Italian Cities - May 2027

4.8

(162 reviews )

No booking fees

Best price guaranteed

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

15% OFF TODAY

Duration10 days

From

USD 2,875

USD 2,449

Saving

USD 426

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7% OFF TODAY

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

7% OFF TODAY

Duration11 days

From

USD 4,999

USD 4,649

Saving

USD 350

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Sicily and Its Isles - May 2027

No booking fees

Best price guaranteed

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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Small Group Tour of Assisi - May 2027

No booking fees

Best price guaranteed

Come to Assisi and explore with a guide the history, art and local traditions of one of the most famous hill towns of Italy. Meet the guide and from there the tour will take you to the old Roman ruins of the local amphitheater, which was reused in the Middle Ages as a quarry for stones to build local houses. You will see how the amphitheatre was turned into a private neighbourhood. From here the view towards the Rocca Maggiore Medieval castle is one of the best in the city. Walk through narrow alleys and medieval squares until you reach Saint Rufino’s Cathedral, Saint Claire's Basilica and the main city square, Piazza del Comune. At the square you will see of the best preserved Roman temple of Italy – Minerva Temple – which is surrounded by imposing medieval government buildings. The tour will then head down to Saint Francis Basilica, which is famous worldwide for its 13th–14th-century frescoes by the best painters of Italy at that time. Among those, the most famous is Giotto.

Walking tours

Tour Type

Small Group Tour

Age Range

5-79 yrs

Operated in

english

Destinations

Assisi

Duration3 hours

From

USD 53

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5% OFF TODAY

Venice and Croatian Islands Cruise - May 2027

No booking fees

Best price guaranteed

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

5% OFF TODAY

Duration13 days

From

USD 4,999

USD 4,749

Saving

USD 250

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Sardinia Adventure - May 2027

No booking fees

Best price guaranteed

Sardinia is a showcase of classic Mediterranean beauty with turquoise seas, pale-gold sands and dramatic rock formations. But with an adventurous spirit and the best tour leader around, you’ll experience its natural wonders from angles most never reach. Staying at a family-run hotel in the Dorgali area, we hike the mighty Gorropu Gorge, cycle through pinewoods to a golden beach (barbecue included), and kayak along the coast to discover sea coves and secret grottoes. Pack your sense of adventure, leave the rest to Sardinia and your tour leader.

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Dorgali, Gorropu Gorge, Cala Lun

Dorgali, Gorropu Gorge, Cala Luna, Tiscali

Duration7 days

From

USD 2,100

USD 2,037

Saving

USD 63

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Walks & Food of the Italian Riviera - May 2027

No booking fees

Best price guaranteed

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

No booking fees

Best price guaranteed

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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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 71 Trips in Italy during May 2027 with 3,177 Reviews

See Italy tours by duration

Page 5 of 71 Trips in Italy during May 2027 with 3,177 Reviews

Walking The Amalfi Coast - Summer Edition - May 2027

Southern Italy & Sicily featuring Taormina, Matera and the Amalfi Coast - May 2027

Spotlight on Northern Italy featuring Venice, Verona & the Dolomites - May 2027

Splendours of Italy - May 2027

Contrasts of Italy - May 2027

Country Roads of Italy, a Women-Only Tour - May 2027

Great Italian Cities - 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

Small Group Tour of Assisi - May 2027

Venice and Croatian Islands Cruise - May 2027

Sardinia Adventure - May 2027

Walks & Food of the Italian Riviera - May 2027

Journeys: Northern Italy, Venice to Florence - May 2027

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 5 of 71 Trips in Italy during May 2027 with 3,177 Reviews

See Italy tours by duration

Page 5 of 71 Trips in Italy during May 2027 with 3,177 Reviews