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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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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
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  • 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
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  • Duration
    1 day26 days

    • See Italy tours by duration

    Showing 1 - 10 of 181 results
    The Marco Polo - May 2026

    The Marco Polo - May 2026

    Experience Italy’s most iconic cities on 'The Marco Polo,' a 4-day guided art and architecture tour from Rome to Venice via Florence and Bologna. Witness Michelangelo’s David, stroll Florence’s cobbled alleys, and float along Venice’s dreamy canals. This easy-paced group tour welcomes families, seniors, and young adults, offering ample opportunities to explore monuments, churches, and charming shops. The standout feature is its immersive, whirlwind introduction to Italy’s artistic and architectural masterpieces, making it an ideal short escape for travelers eager to soak up the country’s timeless beauty.
    Art and architectureChill out
    Tour Type
    Group Tour
    Accommodation
    Hotel
    Age Range
    8-99 yrs
    Operated in
    english
    Destinations
    Rome, Florence, Venice, Lazio
    Rome, Florence, Venice, Lazio
    View Tour
    Sicilian Fantasy: Small Group Tour - May 2026

    Sicilian Fantasy: Small Group Tour - May 2026

    Journey across the Mediterranean's largest island to sample local olive oils and citrus fruits from ancient royal towns, stand among the ruins of proud empires, and venture across Mount Etna’s otherworldly lava fields. Experience a land where medieval villages cling to mountainsides and twisting lanes invite you to stroll down unexpected paths. There’s nothing like your first taste of Sicily—just pair a local dessert wine with a fresh coastal breeze, and you’ll understand how life is truly meant to be savoured
    Cultural, religious and historic sites
    Tour Type
    Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
    Accommodation
    Hotel
    Age Range
    7-99 yrs
    Operated in
    english
    Destinations
    Palermo, Taormina, Agrigento, Sicily
    Palermo, Taormina, Agrigento, Sicily
    View Tour
  • Start & End Location
    • Rome Revealed: A Classic City Break - May 2026

    Rome Revealed: A Classic City Break - May 2026

    Step into the heart of ancient Rome with the "Rome Revealed: A Classic City Break" tour package. Perfect for families, young adults, and seniors, this 4-day trip includes 4-star hotel accommodation, seamless private transfers, and guided tours of the city’s most iconic sites. Explore the Vatican Museums, marvel at the Sistine Chapel, and walk among the ruins of the Roman Forum and Colosseum. With entrance tickets and professional guides included, this city break delivers an immersive and hassle-free Roman experience. The unique selling point: expertly curated access to the city’s legendary history, making every moment in the Eternal City memorable.
    Explorer
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    12-99 yrs
    Operated in
    english
    Destinations
    Milan, Rome
    Milan, Rome
    View Tour
    Best Of Puglia: Small Group Tour - May 2026

    Best of Puglia: Small Group Tour - May 2026

    Discover the heart of Puglia on a perfectly paced tour that blends history, charm, and culture. From the lively streets of Bari to the fairytale Trulli of Alberobello, the cave city of Matera, the elegant baroque towns of Lecce and Martina Franca, and the coastal gems of Otranto and Monopoli — this immersive experience showcases the best of Italy’s hidden south. With UNESCO sites, whitewashed hilltowns, and panoramic Adriatic views, this is Southern Italy at its finest
    Explorer
    Tour Type
    Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
    Accommodation
    Hotel
    Age Range
    12-99 yrs
    Operated in
    english
    Destinations
    Bari, Alberobello, Lecce
    Bari, Alberobello, Lecce
    View Tour
    Timeless Tuscany: A Tuscan Villa Experience - May 2026

    Timeless Tuscany: A Tuscan Villa Experience - May 2026

    Experience the heart of Tuscany with a gastronomic escape at a historic Tuscan villa. This deliciously curated package includes hands-on cooking and pizza-making classes with the warm and welcoming chef, plus a scenic wine tasting at a local farm near San Gimignano. Enjoy time to relax or explore the nearby medieval gems of Siena and Florence, all while staying in a villa once home to popes and princes. With unforgettable meals, charming towns, and authentic Tuscan hospitality, this is the perfect getaway for food and wine lovers seeking a true taste of Italy
    Explorer
    Tour Type
    Private Tour
    Accommodation
    Hotel, Villa
    Age Range
    7-99 yrs
    Operated in
    english
    Destinations
    Tuscany, San Gimignano
    Tuscany, San Gimignano
    View Tour
    Enchanting Cinque Terre From Milan - May 2026

    Enchanting Cinque Terre from Milan - May 2026

    Discover the best of Northern and Central Italy on this 6-day journey. Begin in stylish Milan before traveling to Genoa, a historic port city with a rich maritime heritage. Continue to La Spezia, the gateway to the breathtaking Cinque Terre, where pastel-colored villages cling to dramatic cliffs. With your Cinque Terre Train Card, explore the villages at your own pace, from Riomaggiore to Monterosso. End your adventure in the Eternal City of Rome, where ancient wonders and vibrant piazzas await
    Explorer
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    7-99 yrs
    Operated in
    english
    Destinations
    Milan, Rome, Genoa, La Spezia, Cinque Terre
    Milan, Rome, Genoa, La Spezia, Cinque Terre
    View Tour
    Sardinian Splendours: A 7-day Small Group Tour - May 2026

    Sardinian Splendours: A 7-Day Small Group Tour - May 2026

    Discover the heart and soul of Sardinia on this 7-day small group journey, from historic Cagliari to the luxurious Costa Smeralda—featuring vibrant cities, traditional shepherds’ feasts, ancient Nuragic sites, and breathtaking coastal views. Along the way, explore hilltop villages, immerse yourself in Sardinian culture, and savor the island’s rich culinary heritage with local food and wine experiences. With handpicked accommodations, seamless transportation, and expert local guides, this tour offers an unforgettable blend of authenticity, comfort, and discovery
    Explorer
    Tour Type
    Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
    Accommodation
    Hotel
    Age Range
    7-99 yrs
    Operated in
    english
    Destinations
    Cagliari, Olbia, Alghero
    Cagliari, Olbia, Alghero
    View Tour
    Rome & La Dolce Vita Experience - May 2026

    Rome & La Dolce Vita Experience - May 2026

    Delight in the art of Italian living on the "Rome & La Dolce Vita Experience," a six-day tour that captures the essence of Rome, Sorrento, and beyond. Begin with a culinary journey through Trastevere, savoring authentic Roman dishes with a local expert, before enjoying privileged VIP access to the Vatican Museums. Travel to Pompeii for an evocative walk among ancient ruins, then unwind on the Amalfi Coast with refreshing sea breezes in Sorrento and Capri. With easy-paced city sightseeing, this tour is ideal for families, seniors, and food lovers alike. Its unique selling point is the harmonious blend of cultural immersion and gourmet experiences, wrapped in Italian elegance.
    City sightseeing
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    6-99 yrs
    Operated in
    english
    Destinations
    Rome, Lazio, Sorrento
    Rome, Lazio, Sorrento
    View Tour
    La Dolce Vita Experience - May 2026

    La Dolce Vita Experience - May 2026

    Yearning for a taste of Italy’s famous dolce vita? The 'La Dolce Vita Experience' is a 3-day private cultural, religious, and historic tour beginning and ending in Rome. Travel through Lazio and Sorrento, passing medieval villages and the evocative ruins of Pompeii. Take in Sorrento’s coastal tranquility and visit Capri’s enchanting Blue Grotto. With an easy activity rating and a focus on comfort, this journey is perfect for seniors, young adults, and families seeking a relaxed, intimate escape. The unique selling point: a harmonious blend of history, scenic beauty, and local charm, tailored for those who crave an authentic yet leisurely Italian experience.
    Cultural, religious and historic sites
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    6-99 yrs
    Operated in
    english
    Destinations
    Rome, Lazio, Sorrento
    Rome, Lazio, Sorrento
    View Tour
    Rome & Capri Escape - May 2026

    Rome & Capri Escape - May 2026

    Step into the heart of Italy with a journey that blends timeless history and Mediterranean magic. Begin in Rome, where ancient wonders like the Colosseum, Roman Forum, and Vatican City reveal the Eternal City’s unmatched grandeur. Then trade bustling piazzas for the sparkling waters of Capri, an island of elegance and natural beauty. From chic boutiques and lemon-scented lanes to the dazzling Blue Grotto and sweeping coastal views, this escape offers the best of Italy — culture, romance, and la dolce vita — in one unforgettable adventure
    Explorer
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    6-99 yrs
    Operated in
    english
    Destinations
    Rome
    Rome
    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.

  • Price
    USD 30USD 11,866

    • Page 18 of 181 Trips in Italy during May 2026 with 2,912 Reviews

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