All Italy Tours in May 2026

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Page 2 of 202 Trips in Italy during May 2026 with 3,345 Reviews

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Explore Malta 5 Days, Self-drive - May 2026

Trip customizable

Best price guaranteed

Discover the best of Malta during this short self-drive tour! Walk through the streets of La Valletta, often referred to as “the city built by gentlemen for gentlemen”, the capital of Malta offers both culture and relaxation. Visit the famous Mosta Basilica, which is the third-largest in Europe and one of the main highlights of Malta.

Art and architecture

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Sliema, St Julian's, Sliema

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Duration5 days

Via Francigena: Orvieto to Rome - May 2026

4.5

(8 reviews )

No booking fees

Best price guaranteed

A truly memorable holiday which enabled us not only to see parts of the wonderful Lazio countryside that we wouldn’t normally see by car, but also to soak up the atmosphere of the various villages and towns where we stayed.

Walking tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Rome, Orvieto, Bolsena, Montefia

Rome, Orvieto, Bolsena, Montefiascone, Viterbo, Vetralla, Sutri, Campagnano Di Roma, Isola Farnese, Piazza San Pietro

Duration10 days

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Sicily Food & Wine - May 2026

4.7

(40 reviews )

No booking fees

Best price guaranteed

Sicily is a fascinating treasure trove of history and beauty. This trip allows you to experience the Sicilian way of life using food as a lure to explore its villages, towns and landscape as you move from one side of the island to the other.

Food tours

Tour Type

Small Group Tour

Accommodation

Lodge, Villa, Bungalow, Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Palermo, Taormina, Marsala, Agri

Palermo, Taormina, Marsala, Agrigento, Sicily, Syracuse, Catania

Duration8 days

Best of Italy - May 2026

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Best price guaranteed

Be whisked away into the beauty and history of Italy when you journey to Venice, Florence, and Rome. Journey to the wine-producing Romagna countryside for a relaxing two-night stay in a wine resort, and visit the Republic of San Marino, an enclave state of Italy. See how gondola oars are crafted before cruising the canals of Venice on one yourself. Witness a performance of Vivaldi’s famous Four Seasons in the city he lived in. Explore Orvieto, an ancient Etruscan hilltop city. Try your hand at making Italian culinary classics before sitting down to dinner. Discover Rome’s artistic masterpieces. Come along with us and embrace the history, culture, art and romance of this incredible country.

Art and architecture

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

1-99 yrs

Operated in

english

Destinations

Rome, Venice, Romagna, Florence

Duration12 days

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Italy's Treasures Art, Food & Wine of Italy - May 2026

(1 review )

No booking fees

Best price guaranteed

The tour was great from beginning to the end. The tour guide was awesome , very professional and courteous.The itinerary was filled with great experiences which were memorable. I would highly recommend this tour.

Food toursWine tasting tours

Tour Type

Group Tour

Accommodation

Villa, Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Venice, Lombardy & the Lakes, St

Venice, Lombardy & the Lakes, Stresa, Italian Riviera, Tuscany

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Duration12 days

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Explore Malta 7 Days, Self-drive - May 2026

Trip customizable

Best price guaranteed

Discover the best of Malta during this seven-day self-drive tour! Walk through the streets of La Valletta, often referred to as “the city built by gentlemen for gentlemen”, the capital of Malta offers both culture and relaxation. Visit the famous Mosta Basilica, which is the third-largest in Europe and one of the main highlights of Malta.

Art and architecture

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Sliema, St Julian's, Sliema

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Duration7 days

Classic Amalfi Coast - 8 Days - May 2026

4.8

(9 reviews )

No booking fees

Best price guaranteed

It was very well organised. Everything worked smoothly, we had a great holiday.

Walking tours

Tour Type

Private Tour

Accommodation

Hotel, Villa

Age Range

18-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Positan

Amalfi Coast & Campania, Positano, Amalfi, Maestra Dei Villaggi, Praiano, Naples

Duration8 days

Via Francigena: Best of Tuscany - May 2026

4.6

(28 reviews )

No booking fees

Best price guaranteed

Great trip, all happened as planned.

Trekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Tuscany, Buonconvento, San Minia

Tuscany, Buonconvento, San Miniato Alto, Gambassi Terme, San Gimignano, Gracciano, Monteriggioni, Siena, Lucignano D Arbia

Duration9 days

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.

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Italian Scene - May 2026

4.5

(70 reviews )

No booking fees

Best price guaranteed

The scenery was beautiful. Next time I'd slow it down a bit though and enjoy each city for a few days.

Countryside and village visits

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome

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Duration10 days

Sicily & Amalfi Coast Escape - May 2026

Trip customizable

Best price guaranteed

A trip from Sorrento to Sicily promises a journey filled with scenic beauty, rich history, and vibrant culture. Explore the wonders of the Amalfi Coast, and Sicily on an Italian adventure from Rome! Walk the ruins of Pompeii, soak up the atmosphere along the Sorrentine Coast, and sun-bleached Capri. Discover the Mediterranean island of Sicily through its unique architecture, charming villages, and traditional cuisine. Stroll through endless stretches of stunning beaches and explore the majestic ancient ruins of past empires!

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Sorrent

Amalfi Coast & Campania, Sorrento, Palermo, Rome, Taormina, Agrigento, Sicily

Duration11 days

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Discovering Venice - May 2026

(1 review )

Trip customizable

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Hi, Venice is beautiful. Emanuela was helpful and professional, would definitely travel again with Tui Italy

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Venice

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Duration4 days

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Classic Europe - May 2026

4.8

(70 reviews )

No booking fees

Best price guaranteed

This tour was an amazing experience and a great way to see A LOT of Europe in a short amount of time. The trip was fast paced but very well planned out with the itinerary and mix of activities that you see and do. Jemma, our tour guide was absolutely amazing! We couldn't have asked for better! She was charismatic, funny, knowledgeable, organized, and guided us in a positive way where we got the very most out of the travel experience learning the local history, foods, culture and best site seeing spots. She went above and beyond to make sure we were getting the most out of our tour experience. Gabriel, our driver was also phenomenal. We always felt very safe and he was always perfectly punctual and helped us load/ unload and kept us very comfortable on the coach.

Active and outdoor

Tour Type

Group Tour

Accommodation

Hotel

Age Range

10-99 yrs

Operated in

english

Destinations

Paris, Rome, London, Amsterdam

Paris, Rome, London, Amsterdam, Nuremberg, Beaune, Montecatini Terme, Venice

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Duration14 days

Via Francigena: Southern Tuscany from Siena - May 2026

4.5

(8 reviews )

No booking fees

Best price guaranteed

An amazing walk through the Tuscan countryside. Exceptional organisation and attention to detail meant we could concentrate on having a great time and not have to worry about accommodation, meals and transfers. Thanks!

Trekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Rome, Siena, Lazio, Lucignano D

Rome, Siena, Lazio, Lucignano D Arbia, Tuscany, San Quirico d'Orcia, Castiglione D Orcia, Radicofani

Duration8 days

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Discovering Milan - May 2026

(1 review )

Trip customizable

Best price guaranteed

Join this four-day short break in Milan and discover Sforza Castle the most impressive urban castle in Europe, and Duomo Cathedral, a striking example of Gothic art and the largest church in Italy. Admire the famous Last Supper of Leonardo Da Vinci, enjoy the Navigli district and take a trip to Lake Como and Lugano. Don’t miss the shopping opportunity as Milan is one of the most important cities in the world of fashion.

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

6-99 yrs

Operated in

english

Destinations

Milan

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