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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 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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See Italy tours by duration

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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
  • BBC
  • Independent
  • Lonely Planet
  • Duration
    1 day26 days
  • Physical Rating
  • Tour Types
  • 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.
  • Guide Types
  • Activities
  • Destinations
    • Showing 1 - 10 of 181 results
  • Price
    USD 30USD 11,866
    • Discovering Naples - May 2026

    Discovering Naples - May 2026

    Naples pulses with history and life, and the "Discovering Naples" tour is the perfect introduction for seniors longing for a relaxed yet rich Italian experience. Over four days, this self-guided art and architecture trip lets you uncover the city’s treasures at your own pace—from the sun-dappled waterfront under Vesuvius to the vibrant historic center teeming with centuries-old art and culture. Savor local cuisine, stroll through bustling streets, and soak up Naples’ unique blend of ancient charm and contemporary energy. The charm of this tour lies in its flexibility and depth, offering travelers a comfortable, authentic immersion into one of Italy’s most captivating cities.
    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, italian
    Destinations
    Naples
    Naples
    View Tour
    Discovering Florence - May 2026

    Discovering Florence - May 2026

    Florence, with its Renaissance splendor and Tuscan charm, sets the stage for an enriching four-day art and architecture trip—ideal for senior travelers seeking a relaxed yet culturally rich getaway. Explore iconic landmarks like the Accademia and Uffizi Galleries, marvel at the Duomo Cathedral, and wander through boutique-lined streets. Experience the rustic countryside with a glass of wine in hand, surrounded by rolling hills. This self-guided tour’s unique selling point is its balance of world-class art, leisurely exploration, and the flavors of Tuscany, all in a compact, accessible package.
    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
    Destinations
    Florence
    Florence
    View Tour
    Discovering Syracuse - May 2026

    Discovering Syracuse - May 2026

    Step into the ancient heart of Sicily with the 4-day 'Discovering Syracuse' tour, crafted for seniors who cherish comfort, culture, and culinary delights. This guided art and architecture trip immerses you in Siracusa’s rich tapestry—wander through timeless streets, marvel at historic treasures, and ascend the slopes of Mt. Etna for breathtaking views. Savor authentic Sicilian cuisine and explore the storied centers of Syracuse and Taormina, where vibrant local life meets centuries of architectural splendor. The unique highlight? A seamless blend of gentle adventure and deep cultural immersion, making every day both accessible and unforgettable.
    Art and architecture
    Tour Type
    Group Tour
    Accommodation
    Hotel
    Age Range
    6-99 yrs
    Operated in
    english
    Destinations
    Syracuse
    Syracuse
    View Tour
    Discovering Palermo - May 2026

    Discovering Palermo - May 2026

    Uncover the vibrant tapestry of Palermo on this leisurely four-day tour, designed with comfort and discovery in mind for seniors. As Sicily’s bustling capital, Palermo welcomes you with its unique blend of Arab, Norman, Byzantine, and Mediterranean influences. Enjoy expertly guided art and architecture walks, sample local delicacies, and immerse yourself in centuries of history. This small-group trip ensures you experience the city’s essence without rush, with all accommodations and logistics taken care of. The stand-out feature: direct insights from local experts, bringing Palermo’s layered heritage vividly to life.
    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
    Destinations
    Palermo
    Palermo
    View Tour
    In The Footsteps Of Michelangelo: 7 Days From Florence To Rome, Private Tour - May 2026

    In The Footsteps Of Michelangelo: 7 Days From Florence To Rome, Private Tour - May 2026

    Learn about the life and work of the famous Italian artist Michelangelo Buonarroti! This tour is a deeper insight into his life and art and will be focused on the most important sculptures of this artist. You will have the opportunity to visit the most important sites and highlights of Florence and Rome with our expert guide.
    Art and architecture
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    6-99 yrs
    Operated in
    english, spanish, french, german, italian
    Destinations
    Rome, Florence
    Rome, Florence
    View Tour
    Discovering Rome - May 2026

    Discovering Rome - May 2026

    Rome’s legendary past comes alive on the "Discovering Rome" tour, a self-guided four-day adventure tailored for seniors who appreciate a gentle pace. From ancient ruins to vibrant piazzas, explore a city where every corner reveals layers of history, art, and culinary delights. Wander iconic sites at your leisure, savor authentic Italian flavors, and immerse yourself in the unique ambiance that has captivated visitors for centuries. The standout feature of this trip is its flexibility, allowing you to craft your own Roman holiday while enjoying the support and comfort of a well-organized tour package.
    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
    Rome
    Rome
    View Tour
    Discovering Taormina - May 2026

    Discovering Taormina - May 2026

    Taormina beckons with its sun-soaked shores and ancient stories—perfect for seniors seeking a gently active escape. ‘Discovering Taormina’ is a four-day, small-group art and architecture tour that offers a seamless blend of culture and natural beauty. Wander through the city’s evocative streets, gaze out over the Ionian Sea, and experience the dramatic ascent of Mt. Etna. A coastal cruise and easy walking explorations ensure this trip remains accessible and rewarding. The highlight: the opportunity to combine the allure of Sicily’s history with the thrill of standing atop Europe’s most famous volcano—all at a comfortable, easy pace.
    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, italian
    Destinations
    Taormina
    Taormina
    View Tour
    Discovering Bari - May 2026

    Discovering Bari - May 2026

    Bari, perched elegantly on the Adriatic, invites you to explore its sunlit streets and rich history at a relaxed pace. This four-day self-guided art and architecture tour is crafted for seniors who enjoy independent yet comfortable travel. Tour historic landmarks such as the Basilica di San Nicola and the Museo Nicolaiano, soaking in the fusion of southern Italian sophistication with provincial charm. The trip’s distinct advantage is its balance of cultural exploration and personal freedom, allowing you to discover Bari’s treasures in your own time with all logistics handled.
    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, italian
    Destinations
    Bari
    Bari
    View Tour
    Beautiful Campania - May 2026

    Beautiful Campania - May 2026

    The Beautiful Campania tour offers a gentle 3-day introduction to one of Italy’s most captivating regions. Ideal for seniors, this group sightseeing journey starts and ends in Rome, providing a seamless, worry-free way to enjoy Campania’s historic and culinary highlights. With everything from hotels to meals included, you can focus on soaking up the atmosphere and making lasting memories. The tour’s USP is its efficiency—perfect for those who prefer a short yet thorough Italian getaway.
    City sightseeing
    Tour Type
    Group Tour
    Accommodation
    Hotel
    Age Range
    15-99 yrs
    Operated in
    english
    Destinations
    Rome, Naples
    Rome, Naples
    View Tour
    Discovering Matera - May 2026

    Discovering Matera - May 2026

    Discovering Matera is like stepping into a living canvas—where ancient dwellings carved from stone paint a picture of Italy unlike any other. This four-day self-guided art and architecture tour is crafted for seniors who appreciate both history and tranquility. Meander through winding alleys, marvel at centuries-old houses sculpted from tuff, and absorb the city’s cinematic allure. The USP of this trip is its focus on Matera’s unique landscape and layered history, offering a peaceful yet immersive open-air museum experience.
    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, italian
    Destinations
    Matera
    Matera
    View Tour
  • Start & End Location

    • 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.

    Page 14 of 181 Trips in Italy during May 2026 with 2,912 Reviews

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