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May 2026 tours
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May 2026 Italy Tours - Book Now

Don't miss out on Italy's best experiences! Book early from over 500 tours departing in May 2026. Secure better prices, guaranteed spots, and peace of mind with more than 7,100 verified traveler experiences.

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May 2026 Italy Tours - Book Now

Jan 2026 Feb 2026 Mar 2026 Apr 2026 May 2026 Jun 2026 Jul 2026 Aug 2026 Sep 2026 Oct 2026 Nov 2026

Showing 1 - 10 of 181 results

Duration

1 day26 days

Day Tour
Multiday Tour

Price

USD 30USD 11,866

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Tour Types

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Small group tours
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Age

Young Travelers (Age 18-39)Mature Travelers (Age 40-59)Senior Travelers (Age 60+)

Activities

Art and architecture
Cultural, religious and historic sites
City sightseeing
Explorer
Walking tours

Physical Rating

relaxed
easy
moderate
challenging

Accommodations

BudgetSimple stays with essential amenities. Typically guesthouses, hostels or hotels rated below 3 stars — clean, no-frills, and great for value-conscious travelers.
Mid-rangeComfortable and reliable 3-star stays. Expect private rooms, en-suite bathrooms, and solid amenities — a great balance between comfort and cost.
PremiumUpscale 4-5 star hotels and lodges. Enjoy high-end service, refined comfort, and premium locations — ideal for travelers seeking extra indulgence.

Destinations

Rome
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Sorrento

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Jan 2026 Feb 2026 Mar 2026 Apr 2026 May 2026 Jun 2026 Jul 2026 Aug 2026 Sep 2026 Oct 2026 Nov 2026

Duration

1 day26 days

Day Tour
Multiday Tour

Tour Types

Group tours
Private tours
Small group tours
Independent tours

Activities

Art and architecture
Cultural, religious and historic sites
City sightseeing
Explorer
Walking tours

Physical Rating

relaxed
easy
moderate
challenging

Accommodations

BudgetSimple stays with essential amenities. Typically guesthouses, hostels or hotels rated below 3 stars — clean, no-frills, and great for value-conscious travelers.
Mid-rangeComfortable and reliable 3-star stays. Expect private rooms, en-suite bathrooms, and solid amenities — a great balance between comfort and cost.
PremiumUpscale 4-5 star hotels and lodges. Enjoy high-end service, refined comfort, and premium locations — ideal for travelers seeking extra indulgence.

Destinations

Rome
Venice
Florence
Naples
Sorrento

Guide Types

Guided Tours
Self Guided Tours
Partially Guided Tours

Get a customized trip to Italy in May 2026

Plan a multi-country or regional adventure across Italy in May 2026, with help from a local expert.

Alessandra GalassiTravel Expert in Italy
Elena KyrimiTravel Expert in Greece & Italy
Danilo CataniaTravel Expert in Italy

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Price

USD 30USD 11,866

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Page 16 of 181 Trips in Italy during May 2026 with 2,912 Reviews

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 France and Italy.

Splendours of Sicily - May 2026

Trip customizable

Best price guaranteed

Step into the heart of the Mediterranean with the 'Splendours of Sicily' tour, an 8-day city sightseeing trip beginning and ending in Catania. This thoughtfully guided journey welcomes families, young adults, and seniors alike to experience Sicily's legendary baroque architecture, UNESCO-listed treasures, and captivating local culture. Wander through the storied streets of Catania, marvel at the ancient wonders of Agrigento, and soak in the charm of Campania. With comfortable accommodations, seamless transport, and delicious meals included, travelers of all ages can relax and savor Sicily’s world-renowned cuisine, vibrant traditions, and picturesque landscapes. The unique selling point of this tour is its immersive introduction to Sicily’s layered history and gastronomic delights, all delivered in a leisurely, easy-paced itinerary perfect for families and multi-generational groups. Discover why Sicily is celebrated for its profound beauty, warmth, and cultural richness on this unforgettable tour package.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

13-99 yrs

Operated in

english

Destinations

Catania, Campania, Sicily, Agrig

Catania, Campania, Sicily, Agrigento, Palermo

Duration8 days

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Best of Rome, Florence & Venice - May 2026

Trip customizable

Best price guaranteed

Step onto Italian soil and be swept into a whirlwind of culture, history, and art with the 'Best of Rome, Florence & Venice' tour. Over 7 days, this easy-paced city sightseeing package links three of Italy’s iconic cities, perfectly suited for multigenerational families, seasoned explorers, and travelers eager for a stress-free yet immersive adventure. Travel effortlessly by high-speed train from Rome’s ancient ruins and Vatican treasures to Florence’s Renaissance masterpieces. Wander through bustling piazzas, marvel at the Duomo, and savor the city’s creative spirit before gliding into Venice, whose canals and timeless charm make every moment memorable. With all accommodation, meals, and transport included, you’ll enjoy comfort and convenience throughout. What sets this trip apart is its seamless blend of Italy’s most treasured highlights—delivered in a relaxed, accessible way that lets you experience the essence of each destination at your own pace. For those who want to discover the heart of Italy without the hassle, this tour package is a true standout.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Venice, Lazio, Rome, The Vatican

Venice, Lazio, Rome, The Vatican, Florence

Duration7 days

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Explore Malta 5 Days, Self-drive - May 2026

Trip customizable

Best price guaranteed

Malta’s allure beckons you on the Explore Malta 5 Days, Self-drive tour, designed with seniors in mind for a relaxed, worry-free holiday. Begin and end your trip in Sliema, where charming streets and coastal beauty set the scene for leisurely exploration. Stroll through the historic heart of La Valletta, Malta’s capital—celebrated for its rich architecture and vibrant culture. Marvel at the awe-inspiring Mosta Basilica, one of Europe’s largest, and enjoy the freedom a self-drive tour provides, ensuring each day moves at your own pace. The standout feature of this tour package is its blend of guided comfort and independence, making it a perfect choice for travelers who appreciate both structure and flexibility while enjoying Malta’s cultural treasures.

Art and architecture

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Sliema, St Julian's, Sliema

Duration5 days

Sensational Sicily - May 2026

Trip customizable

Best price guaranteed

Let Sicily’s timeless beauty take center stage on the "Sensational Sicily" tour, a ten-day city sightseeing journey from the island’s heart to its sun-kissed coasts. With easy pacing and a welcoming atmosphere, this group trip is ideal for families, young adults, and seniors seeking to immerse their senses in the island’s vibrant heritage. Marvel at the rugged coastline, tranquil countryside, and rolling hills dotted with ancient towns and UNESCO-listed cities. Every meal is an adventure—sample street food and traditional feasts that celebrate Sicily’s culinary diversity. Along the way, delve into the island’s rich tapestry of art, archaeology, and local traditions. The tour’s unique feature? A harmonious blend of scenic exploration and gastronomic delights, offering a comprehensive introduction to Sicily’s many treasures in one unforgettable package.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

13-99 yrs

Operated in

english

Destinations

Palermo, Catania, Campania, Sici

Palermo, Catania, Campania, Sicily, Agrigento

Duration10 days

Sicily & Amalfi Coast Escape - May 2026

Trip customizable

Best price guaranteed

From Rome’s grandeur to the sun-drenched shores of Taormina, the 'Sicily & Amalfi Coast Escape' is an 11-day guided trip designed to showcase Italy’s most stunning coastlines and historic gems. Explore the ruins of Pompeii, the vibrant Sorrentine Coast, and Capri’s legendary beauty before discovering Sicily’s captivating villages, unique architecture, and traditional cuisine. Ideal for families, seniors, and young adults, this easy-paced tour blends scenic walks, cultural immersion, and leisurely sightseeing. The USP: a seamless combination of Italy’s most celebrated coastal destinations and ancient marvels, ensuring a journey rich in history, culture, and Mediterranean charm.

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

Sicilian Secrets - May 2026

Trip customizable

Best price guaranteed

Unlock the mysteries of Sicily on the 'Sicilian Secrets' tour, a 6-day guided art and architecture trip that lets you travel from Sicily’s bustling cities to its quietest corners, concluding in Palermo. Designed with both young adults and seniors in mind, and welcoming for families, this easy-paced tour offers a blend of archaeological exploration and culinary indulgence. Meander through Agrigento, Campania, Catania, and more, as you sample Sicily’s famous cuisine and delve into the traditions woven into its labyrinthine streets. Connect with locals and experience the authentic rhythms of daily life, where history meets modernity in towns brimming with charm. The USP of this tour is its perfect balance: you’ll discover both celebrated landmarks and hidden gems, ensuring a richly detailed immersion in Sicilian culture that lingers long after your return.

Art and architecture

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

13-99 yrs

Operated in

english

Destinations

Campania, Sicily, Lazio, Catania

Campania, Sicily, Lazio, Catania, Agrigento, Palermo

Duration6 days

A Grand Tour of Puglia's Wonders - May 2026

Trip customizable

Best price guaranteed

Southern Italy’s Puglia region dazzles with its blend of history, coastline, and culinary delights, and 'A Grand Tour of Puglia's Wonders' captures it all in an 8-day sightseeing adventure. Starting and ending in Bari, this guided tour is crafted for families, seniors, and experienced travelers who relish easy-paced cultural exploration. Wander through the seaside beauty of Trani, ascend the spiritual heights of Monte Sant'Angelo, and take in the mystical forest trails of Foresta Umbra. The trip continues with iconic destinations: Alberobello’s trulli houses, the whitewashed streets of Ostuni, and the ancient treasures of Matera. Enjoy the baroque elegance of Lecce, the historic allure of Otranto, and Bari’s vibrant city life. Along the way, savor local cuisine and discover the region’s timeless traditions. The tour’s true highlight is its rich variety—offering a tapestry of coastal vistas, architectural marvels, and immersive experiences ideal for all ages and interests. For those seeking a journey that blends the best of southern Italy’s scenery, history, and food, this tour package is an unbeatable choice.

Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

7-99 yrs

Operated in

english

Destinations

Bari, Monte Sant'Angelo

Duration8 days

Mini Tour of Campania - Coastal Gems - May 2026

Trip customizable

Best price guaranteed

Discover the magic of southern Italy’s coastline with the 'Mini Tour of Campania - Coastal Gems.' This five-day sightseeing adventure, starting and ending in Naples, is a family-friendly escape ideal for seniors, experienced travelers, and young explorers alike. Kick off in Salerno, then journey to picturesque Positano and Amalfi, where scenic beauty meets local hospitality. Savor the region’s culinary excellence with a cheese tasting at a local factory, explore the ancient wonders of Paestum, and bask in the regal splendor of the Royal Palace of Caserta. Conclude your Italian getaway in vibrant Naples, where history and modern energy blend seamlessly. The tour’s standout feature is its immersive approach to local cuisine and culture—ensuring each day is packed with flavors and experiences that create lasting memories for every traveler.

Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Naples

Amalfi Coast & Campania, Naples, Salerno, Paestum

Duration5 days

Treasures of Sicily - May 2026

Trip customizable

Best price guaranteed

Begin your journey in Catania, exploring ancient temples and baroque architecture. Traverse the island to Monreale and Palermo, discovering cathedral treasures and indulging in Sicilian delights. Wander through the picturesque streets of Erice, Siracusa, and Noto. Immerse yourself in the rich history of Agrigento's Valley of the Temples and the Roman Villa in Piazza Armerina. Ascend the iconic Mount Etna, and explore the timeless beauty of Taormina. This curated itinerary blends cultural immersion, gastronomic delights, and natural wonders, ensuring an unforgettable Sicilian adventure

Explorer

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

7-99 yrs

Operated in

english

Destinations

Catania, Noto, Taormina, Palermo

Catania, Noto, Taormina, Palermo, Agrigento, Sicily, Mount Etna

Duration8 days

A Taste of Sicily - May 2026

Trip customizable

Best price guaranteed

Tempt your palate and your wanderlust on "A Taste of Sicily," a five-day culinary adventure from Palermo to Catania. This guided group food tour is perfect for families, seniors, and young explorers eager to experience Sicily’s legendary flavors and coastal scenery. Sample local delicacies, explore seaside villages crowned by medieval castles, and let ancient Greek ruins whisper their stories as you journey through the region. Witness sunsets painting picturesque towns in golden hues, and gaze upon the commanding silhouettes of volcanoes rising from the landscape. The unique selling point of this trip? A delicious fusion of food, history, and hidden gems—offering a deeply immersive slice of Sicilian culture that will leave you craving more.

Food tours

Tour Type

Group Tour

Accommodation

Hotel

Age Range

13-99 yrs

Operated in

english

Destinations

Campania, Sicily, Lazio, Palermo

Campania, Sicily, Lazio, Palermo, Catania