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  • Home
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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 480 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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    • See Italy tours by duration

    Jan 2026Feb 2026Mar 2026Apr 2026May 2026Jun 2026Jul 2026Aug 2026Sep 2026Oct 2026Nov 2026
  • Duration
    1 day26 days
  • Tour Types
  • Activities
  • Physical Rating
  • Accommodations
    • Simple stays with essential amenities. Typically guesthouses, hostels or hotels rated below 3 stars — clean, no-frills, and great for value-conscious travelers.
    • Comfortable and reliable 3-star stays. Expect private rooms, en-suite bathrooms, and solid amenities — a great balance between comfort and cost.
    • Upscale 4-5 star hotels and lodges. Enjoy high-end service, refined comfort, and premium locations — ideal for travelers seeking extra indulgence.
  • Destinations
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    • 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 Galassi - Italy in May 2026 Tours Expert
      Alessandra GalassiTravel Expert in Italy
    • Elena Kyrimi - Italy in May 2026 Tours Expert
      Elena KyrimiTravel Expert in Greece & Italy
    • Danilo Catania - Italy in May 2026 Tours Expert
      Danilo CataniaTravel Expert in Italy
    Start planning your Trip
    Recommended by
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  • Start & End Location
  • Price
    USD 30USD 11,866
    • Showing 1 - 10 of 181 results
    Italy’s Southern Charm: Rome To Puglia - May 2026

    Italy’s Southern Charm: Rome to Puglia - May 2026

    Discover Italy’s timeless charm on this 7-day journey from the Eternal City to the Adriatic coast. Begin in Rome, where ancient history and vibrant street life converge, then head south to explore the ruins of Pompeii and the coastal beauty of Sorrento and Capri. Dive into the flavors and energy of Naples before crossing the country by high-speed train to the charming city of Bari, where Romanesque architecture and seaside strolls await. A perfect blend of culture, history, and local life—crafted for the curious traveler
    Explorer
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    7-99 yrs
    Operated in
    english
    Destinations
    Bari, Rome, Colosseum, Pompeii
    Bari, Rome, Colosseum, Pompeii, Capri, Naples
    View Tour
    A Week In Italy: Rome, Florence & Venice - May 2026

    A Week in Italy: Rome, Florence & Venice - May 2026

    From a private arrival transfer in Rome to high-speed train travel between cities, this carefully curated 7-day Italy itinerary blends iconic landmarks, immersive cultural experiences, and stress-free logistics. Discover ancient wonders like the Colosseum and Roman Forum in the Eternal City; stroll through the Renaissance heart of Florence, home to world-renowned art and architecture; and experience the romance of Venice with an included gondola ride through its historic canals. Featuring a thoughtful mix of expert-guided tours and free time to explore the iconic landmarks of Italy
    Explorer
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    7-99 yrs
    Operated in
    english
    Destinations
    Rome, Venice, Florence
    Rome, Venice, Florence
    View Tour
    Naples Express & Sorrento (on Request) - May 2026

    Naples Express & Sorrento (on Request) - May 2026

    Discover the timeless elegance of the Sorrento peninsula and Capri on the "Naples Express & Sorrento (on Request)" tour, designed for seniors who value history, comfort, and leisurely exploration. Over four days, absorb Naples’ rich heritage, then journey through the evocative ruins of Pompeii before reaching the picturesque coastal charm of Sorrento. Hop a ferry to Capri and explore the legendary Blue Grotto. With self-guided flexibility and all logistics arranged, this tour’s unique appeal lies in its blend of iconic sights and gentle pacing—an ideal art and architecture trip for those who want to experience Italy’s highlights without the rush.
    Art and architecture
    Tour Type
    Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
    Accommodation
    Hotel
    Age Range
    6-99 yrs
    Operated in
    english, spanish
    Destinations
    Naples, Sorrento, Rome
    Naples, Sorrento, Rome
    View Tour
    Islands, Coast And Flavors Of Campania: 8 Days Capri, Ischia & Naples, Private Tour - May 2026

    Islands, Coast And Flavors Of Campania: 8 Days Capri, Ischia & Naples, Private Tour - May 2026

    A consistently mild climate, lush nature framing breath-taking landscapes, unspoilt villages and fairy-tale coastlines: this is Campania, a region that sums up centuries of cultures, between West and East, in a single Mediterranean jewel known for its unparalleled hospitality. A destination for the soul, the eyes and the palate. During this tour you will visit the islands of Capri and Ischia discovering the beauty of nature and enjoy the culinary aspects through a street food tour in the most famous capital of Italian food Naples.
    BeachFood tours
    Tour Type
    Private Tour
    Accommodation
    Hotel, Villa
    Age Range
    6-99 yrs
    Operated in
    english, spanish, french, german, italian
    Destinations
    Naples, Ischia, Capri
    Naples, Ischia, Capri
    View Tour

    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 France and Italy.

    Sorrento Dream (on Request) - May 2026

    Sorrento Dream (on Request) - May 2026

    Experience the magic of Campania with the "Sorrento Dream (on Request)" tour—crafted especially for seniors seeking ease, comfort, and cultural immersion. Over four days, discover the historic streets and waterfront of Sorrento, explore Naples’ rich history, and set sail to the dramatic island of Capri. Marvel at the archaeological wonders of Pompeii, then bask in the stunning scenery and vibrant life along Italy’s southern coast. This self-guided trip ensures flexibility and convenience, with all accommodations, meals, and transport arranged. The tour’s standout feature is its seamless blend of art, history, and breathtaking landscapes—offering a leisurely yet enriching Italian escape.
    Art and architecture
    Tour Type
    Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
    Accommodation
    Hotel
    Age Range
    6-99 yrs
    Operated in
    english, spanish
    Destinations
    Sorrento, Rome
    Sorrento, Rome
    View Tour
    Sicily Explorer: 11 Days From Palermo To Palermo, Self-drive - May 2026

    Sicily Explorer: 11 Days From Palermo To Palermo, Self-drive - May 2026

    Discover the beauties of Sicily during this eleven days self-drive tour. Immerse yourself in rich Greek and Roman history, culture and architecture. Drive through several UNESCO Heritage Sites and unique towns, and admire splendid views and art masterpieces. Climb the magnificent Mt Etna volcano and enjoy lunch with the stunning views.
    Self-drive or vehicle rental
    Tour Type
    Private Tour
    Accommodation
    Hotel, Villa
    Age Range
    6-99 yrs
    Operated in
    english
    Destinations
    Palermo, Taormina, Syracuse, Not
    Palermo, Taormina, Syracuse, Noto, Agrigento
    View Tour
    Puglia & Salento Discovery: 8 Days From Bari To Lecce, Self-drive - May 2026

    Puglia & Salento Discovery: 8 Days From Bari To Lecce, Self-drive - May 2026

    Embark on an unforgettable eight-day self-drive adventure through the stunning Puglia region, where you can explore at your own pace and immerse yourself in Italy’s rich culture, fascinating history, and mouthwatering cuisine. Indulge in authentic local flavors, visit UNESCO World Heritage sites, and experience the warm hospitality that makes Puglia a truly special destination.
    Self-drive or vehicle rental
    Tour Type
    Private Tour
    Accommodation
    Hotel, Resort
    Age Range
    6-99 yrs
    Operated in
    english
    Destinations
    Bari, Martina Franca, Otranto
    Bari, Martina Franca, Otranto, Lecce
    View Tour
    A Taste Of Italy: 11 Days - Premium - May 2026

    A Taste of Italy: 11 Days - Premium - May 2026

    Traveling from eternal Rome and up through the hazy hills of Tuscany, you’ll spend eleven days sampling the best of Assisi, Siena, Florence, Bologna, Venice, the Tuscan wine region, and Capri! Catch the spirit of la vita bella as you explore elegant Florentine piazzas, rummage through handcrafted artisanal treasures, sip world-class wines, and float down intimate Venetian canals. You will then discover the treasures along Italy’s Amalfi Coast, to sun-bleached Capri before returning to Rome!
    Explorer
    Tour Type
    Group Tour
    Accommodation
    Hotel
    Age Range
    7-99 yrs
    Operated in
    english
    Destinations
    Rome, Florence, Venice, Sorrento
    Rome, Florence, Venice, Sorrento
    View Tour
    Discovering Bologna - May 2026

    Discovering Bologna - May 2026

    Craving an authentic taste of Italian culture? This four-day tour package in Bologna is an ideal choice for seniors and lovers of fine living. Uncover culinary secrets in a hands-on cooking class with a local Cesarina, savoring the flavors of traditional Bolognese cuisine. Pedal through the city’s historic streets on a guided bike tour, immersing yourself in its vibrant atmosphere and architectural beauty. The tour also whisks you into Italy’s Motor Valley, where exclusive museum and factory visits bring the legends of Ferrari and Lamborghini to life. Blending gourmet delights, cultural depth, and automotive passion, the USP of this trip is its unique fusion of food, art, and motoring heritage—all set within the charismatic charm of Bologna.
    Art and architectureExplorer
    Tour Type
    Group Tour
    Accommodation
    Hotel
    Age Range
    6-99 yrs
    Operated in
    english, italian
    Destinations
    Bologna
    Bologna
    View Tour
    Discovering Amalfi Coast - May 2026

    Discovering Amalfi Coast - May 2026

    The Amalfi Coast’s sun-drenched cliffs and ancient ruins beckon on this four-day art and architecture trip, designed for seniors seeking a relaxed yet enriching escape. Explore the timeless streets of Pompeii and Ercolano, sail to the enchanting island of Capri, and meander through charming pedestrian alleys—all at your own pace. With carefully selected accommodations and seamless logistics, this tour package’s unique appeal lies in its self-guided flexibility, letting you soak in the region’s history and flavors without the crowds.
    Art and architecture
    Tour Type
    Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
    Accommodation
    Hotel, Villa
    Age Range
    6-99 yrs
    Operated in
    english
    Destinations
    Amalfi Coast & Campania, Amalfi
    Amalfi Coast & Campania, Amalfi
    View Tour

    Page 12 of 181 Trips in Italy during May 2026 with 2,912 Reviews

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