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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 6,900 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
    Timeless Southern Italy: Rome, Sorrento & Puglia - May 2026

    Timeless Southern Italy: Rome, Sorrento & Puglia - May 2026

    From the Eternal City of Rome to the sun-kissed shores of Sorrento and the enchanting island of Capri, the adventure continues across Puglia’s most iconic treasures—Alberobello’s Trulli, Matera’s ancient cave dwellings, Lecce’s baroque elegance, and the coastal charm of Otranto and Monopoli. With a mix of guided sightseeing, cultural experiences, and culinary delights, this 12-day tour offers the perfect balance of discovery and leisure through Italy’s most captivating southern landscapes
    Explorer
    Tour Type
    Group Tour
    Accommodation
    Hotel
    Age Range
    12-99 yrs
    Operated in
    english
    Destinations
    Bari, Rome, Lecce, Sorrento, Cap
    Bari, Rome, Lecce, Sorrento, Capri, Alberobello, Matera
    View Tour
    Tuscany Escape: 7 Days Through Art, Wine & Hills, Self-drive - May 2026

    Tuscany Escape: 7 Days Through Art, Wine & Hills, Self-drive - May 2026

    Experience the magic of Tuscany on this 7-day self-drive tour, exploring rolling hills, medieval villages, and charming towns steeped in history. Wander through Renaissance Florence, admire Pisa’s iconic Leaning Tower, and soak in Siena’s Gothic splendor. Discover the world-famous Chianti wine region with its scenic vineyards, olive groves, and hilltop villages, and wander the cobbled streets of San Gimignano, a UNESCO World Heritage Site renowned for its towers and gelato. Enjoy a journey that blends culture, gastronomy, and breathtaking landscapes at your own pace.
    Self-drive or vehicle rental
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    6-99 yrs
    Operated in
    english
    Destinations
    Florence, Chianti
    Florence, Chianti
    View Tour
    Classic Italy & The Italian Riviera - May 2026

    Classic Italy & the Italian Riviera - May 2026

    From the timeless beauty of Rome, Florence, and Venice to the coastal charm of Portofino and the colorful villages of Cinque Terre, discover Italy’s rich cultural heritage, breathtaking landscapes, and culinary delights. Travel in comfort by deluxe coach and high-speed train, enjoy guided visits to iconic sites, sample regional specialties, and ride the legendary Bernina Express through the Swiss Alps. This itinerary blends classic cities, coastal gems, and alpine wonder into one unforgettable Italian adventure
    Explorer
    Tour Type
    Group Tour
    Accommodation
    Hotel, Resort
    Age Range
    12-99 yrs
    Operated in
    english
    Destinations
    Rome, Venice, Florence, Milan, L
    Rome, Venice, Florence, Milan, Liguria, Cinque Terre
    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.

    Beautiful Campania And Sicily - May 2026

    Beautiful Campania and Sicily - May 2026

    Dive into the heart of southern Italy with the Beautiful Campania and Sicily tour, a 5-day easy-paced city sightseeing adventure perfect for seniors. Begin in Rome and journey through Salerno, Taormina, and Palermo, all while enjoying group camaraderie and guided exploration. With accommodations, transport, and meals provided, you’ll have more time to appreciate the history, cuisine, and warm hospitality of each stop. The highlight of this tour is its efficient yet comprehensive route, ensuring you witness the best of Campania and Sicily without feeling rushed.
    City sightseeing
    Tour Type
    Group Tour
    Accommodation
    Hotel, Villa
    Age Range
    15-99 yrs
    Operated in
    english
    Destinations
    Rome, Palermo, Salerno, Taormina
    Rome, Palermo, Salerno, Taormina
    View Tour
    Sicily And Eolic Islands - May 2026

    Sicily and Eolic Islands - May 2026

    Sicily and Eolic Islands invites mature travelers to discover the wonders of Palermo, Agrigento, Taormina, and Milazzo over 8 relaxed days. This guided city sightseeing tour provides all the comforts—accommodation, transport, and meals—so you can focus on sampling local delicacies and admiring ancient sites. For those seeking a serene Mediterranean getaway, the tour’s unique appeal lies in its combination of Sicily’s history with the tranquil beauty of the Eolic Islands.
    City sightseeing
    Tour Type
    Group Tour
    Accommodation
    Hotel
    Age Range
    15-99 yrs
    Operated in
    english
    Destinations
    Palermo, Milazzo, Taormina, Agrigento
    Palermo, Milazzo, Taormina, Agrigento
    View Tour
    Highlights Of Northern Italy: Small Group Tour - May 2026

    Highlights of Northern Italy: Small Group Tour - May 2026

    Embark on an unforgettable 8-day small group journey through Northern Italy, from Milan to romantic Venice, with breathtaking experiences along the way. Ride the world-famous Bernina Express through the Swiss Alps, wander the colorful coastal villages of the Cinque Terre, and explore the elegance of Portofino. Indulge in local food and wine tastings in Liguria and Modena, and dive into Italian automotive excellence at the Ferrari Museum. With hand-picked hotels, expert local guides, and unique culinary moments, this tour blends culture, scenery, and flavour for the perfect Northern Italian trip
    Explorer
    Tour Type
    Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
    Accommodation
    Hotel, Resort
    Age Range
    7-99 yrs
    Operated in
    english
    Destinations
    Milan, Venice, Liguria, Cinque Terre
    Milan, Venice, Liguria, Cinque Terre
    View Tour
    Campania Thermal Baths, Private Tour - May 2026

    Campania Thermal Baths, Private Tour - May 2026

    Immerse yourself in wellness and natural beauty on the Campania Thermal Baths, Private Tour, an indulgent seven-day itinerary crafted for seniors seeking relaxation. From Naples, journey to Ischia and enjoy a panoramic tour of the island’s renowned thermal sites, including Negombo and Poseidon Gardens, with their healing waters. Savor local wines at Casa D’Ambra and take in the picturesque town of Forio, set between Mount Epomeo and the sparkling sea. The unique selling point: a focus on therapeutic spa experiences and local flavors, making this a rejuvenating escape in Italy’s scenic south.
    Art and architecture
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    6-99 yrs
    Operated in
    english
    Destinations
    Naples, Ischia
    Naples, Ischia
    View Tour
    In The Footsteps Of Caravaggio: 6 Days From Florence To Naples, Private Tour - May 2026

    In The Footsteps Of Caravaggio: 6 Days From Florence To Naples, Private Tour - May 2026

    Walk in the footsteps of Caravaggio, from the elegance of Florence through the churches of Rome to the vibrant streets of Naples. Admire his masterpieces in the Uffizi Gallery, discover the emotional power of his paintings in Rome’s San Luigi dei Francesi and Villa Borghese, and trace his dramatic journey through the churches and palaces that still preserve his genius. In Naples, explore the Baroque splendor of Palazzo Zevallos and Pio Monte della Misericordia, where his final works reveal the deep humanity behind his art. A journey through light and shadow, art and passion — just like Caravaggio himself
    Art and architecture
    Tour Type
    Private Tour
    Accommodation
    Hotel, Villa
    Age Range
    6-99 yrs
    Operated in
    english, spanish, french, italian, german
    Destinations
    Florence, Naples, Rome
    Florence, Naples, Rome
    View Tour
    A Taste Of Italy: 11 Days - Classic - May 2026

    A Taste of Italy: 11 Days - Classic - 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!
    Cultural, religious and historic sites
    Tour Type
    Group Tour
    Accommodation
    Hotel
    Age Range
    7-99 yrs
    Operated in
    english
    Destinations
    Rome, Florence, Venice, Lazio, Sorrento
    Rome, Florence, Venice, Lazio, Sorrento
    View Tour
    Discovering Garda Lake - May 2026

    Discovering Garda Lake - May 2026

    Imagine serene mornings by Italy’s largest lake, where crystal-clear waters mirror rolling hills and historic villages. The Discovering Garda Lake tour is a relaxed 4-day art and architecture journey, perfectly suited for seniors seeking a gentle yet enriching escape. With Lake Garda and Sirmione as your backdrops, enjoy guided explorations of charming towns, boat rides, and swimming in the inviting waters. This group trip provides seamless transport, accommodation, and meals, so you can focus on soaking in the area’s natural beauty, historical curiosity, and cultural encounters. The unique selling point is the harmonious blend of leisure and discovery, inviting you to unwind while uncovering the timeless appeal of Lake Garda and its surroundings.
    Art and architecture
    Tour Type
    Group Tour
    Accommodation
    Hotel, Villa
    Age Range
    6-99 yrs
    Operated in
    english
    Destinations
    Lake Garda, Sirmione
    Lake Garda, Sirmione
    View Tour

    Page 11 of 181 Trips in Italy during May 2026 with 2,912 Reviews

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