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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.

  • Age
  • Discounts

    • See Italy tours by duration

    Dec 2025Jan 2026Feb 2026Mar 2026Apr 2026May 2026Jun 2026Jul 2026Aug 2026Sep 2026Oct 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
  • Guide Types

    • 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 477 results
    Splendid Tour (on Request) - May 2026

    Splendid Tour (on Request) - May 2026

    4
    Discover some of the most essential parts of Italy on this five-day cultural trip, beginning with an exploration of the ruins of ancient Pompeii and continuing to the magnificent views of Positano and its surrounding fishing villages.
    Art and architecture
    Tour Type
    Group Tour
    Accommodation
    Hotel
    Age Range
    6-99 yrs
    Operated in
    english, spanish
    Destinations
    Rome, Sorrento, Amalfi
    Rome, Sorrento, Amalfi
    View Tour
    Lake Como Walking - May 2026

    Lake Como Walking - May 2026

    4.9
    Great hotel, good challenging walks and beautiful scenery.
    Active and outdoor
    Tour Type
    Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
    Accommodation
    Hotel, Villa
    Age Range
    16-79 yrs
    Operated in
    english
    Destinations
    Milan, Gravedona, Livo, Bellagio
    Milan, Gravedona, Livo, Bellagio, Como, Dongo
    View Tour
    Discover Tuscany: Culture, Food & Wine - May 2026

    Discover Tuscany: Culture, Food & Wine - May 2026

    5
    This tour was an amazing way to experience the heart of Tuscany. The itinerary was perfectly balanced with cultural visits, delicious food and wine experiences, and plenty of free time to explore or relax. Some highlights for me were the guided tour of Siena, where we tasted incredible pastries made from unique local recipes, the pasta-making class in Chianti with a warm and welcoming family, and the wine tastings at beautiful family-run estates where we learned so much about what we were enjoying. Our day in Florence was equally wonderful. The hotel in Pancole was cozy and inviting and all the family and staff were so welcoming, and our tour leader made everything smooth and enjoyable. A fantastic trip filled with unforgettable memories!
    Active and outdoor
    Tour Type
    Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
    Accommodation
    Hotel, Villa
    Age Range
    18-99 yrs
    Operated in
    english
    Destinations
    Siena
    Siena
    View Tour
    Via Francigena: Best Of Tuscany - May 2026

    Via Francigena: Best of Tuscany - May 2026

    4.6
    The trip was well organized with some of the hotels on the trip being real gems especially the one in the agriturismo and the one in Monteriggioni. The team was responsive when I had questions both before and during the trip and the app was easy to use. We had a fantastic time and the route was gorgeous.
    Trekking and Hiking
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    18-99 yrs
    Operated in
    english
    Destinations
    Tuscany, Buonconvento, San Minia
    Tuscany, Buonconvento, San Miniato Alto, Gambassi Terme, San Gimignano, Gracciano, Monteriggioni, Siena, Lucignano D Arbia
    View Tour
    Cycle Puglia - May 2026

    Cycle Puglia - May 2026

    4.9
    Massimo was a fantastic leader and the combination of itinerary and his knowledge gave us a uniwue experience and insight into this lovely partbof Italy.
    Bicycle tours
    Tour Type
    Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
    Accommodation
    Hotel, Hut
    Age Range
    16-99 yrs
    Operated in
    english
    Destinations
    Altamura, Monopoli, Matera, Albe
    Altamura, Monopoli, Matera, Alberobello, Locorotondo, Savelletri
    View Tour
    Discovering Milan - May 2026

    Discovering Milan - May 2026

    4
    Experience Milan at its most captivating on this four-day self-guided art and architecture trip, tailored for seniors who relish cultural discovery at an unhurried pace. Explore Sforza Castle—Europe’s most impressive urban fortress—and the awe-inspiring Duomo Cathedral. Admire Leonardo da Vinci’s Last Supper, stroll the trendy Navigli district, and take a day trip to Lake Como and Lugano. With shopping opportunities in one of the world’s fashion capitals, this tour’s unique selling point is its seamless blend of history, art, and modern style, all within Italy’s vibrant northern hub.
    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
    Milan
    Milan
    View Tour
    Cycle Puglia - May 2026

    Cycle Puglia - May 2026

    4.8
    Puglia was beautiful. They did a great job of coordinating bikes, luggage, and routes. The lodging was great for our 7 night stays, except for 1 night, when our group was split into 2 different hotels that were not very close with no advance warning.
    Bicycle tours
    Tour Type
    Private Tour
    Accommodation
    Hotel, Resort
    Age Range
    18-99 yrs
    Operated in
    english
    Destinations
    Matera, Lecce, Alberobello, Ostu
    Matera, Lecce, Alberobello, Ostuni, Gallipoli, Santa Maria Di Leuca, Otranto
    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.

    Amalfi Coast Walking - Agriturismo - May 2026

    Amalfi Coast Walking - Agriturismo - May 2026

    4.7
    Excellent farm stay. Good itinerary, knowledgeable guide who looked after everyone. Good food, friendly host family.
    Walking toursFood tours
    Tour Type
    Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
    Accommodation
    Resort, Villa, Hotel
    Age Range
    16-99 yrs
    Operated in
    english
    Destinations
    Naples
    Naples
    View Tour
    Ancient Sicily - May 2026

    Ancient Sicily - May 2026

    4.7
    You really do need two weeks to cicumnavigate Sicily and see things properly. Any shorter and you'll get just a couple highlights or get very rushed from place to place. This tour had good pace, gave sufficient time in major sites (Syracuse, Agrigento, Palermo, Villa del Casale) and included gems like Morgantina, Mozia Island, and Enna. Antonio is an exceptional wealth of information, its obvious he has a professional background in Sicilian history. The level of historical, cultural and architectural background information was tremendous, helped greatly to put things in context and understand the flow and changes absorbed by this island that resulted in what we were seeing.
    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, Villa, Resort
    Age Range
    16-99 yrs
    Operated in
    english
    Destinations
    Syracuse, Sicily, Palermo, Giard
    Syracuse, Sicily, Palermo, Giardini Naxos, Catania, Taormina, Piazza Amerina, Piazza Armerina, Agrigento, Marsala, Mozia Island
    View Tour
    Via Francigena: Lucca To Siena - May 2026

    Via Francigena: Lucca to Siena - May 2026

    4.6
    Amazing experience. It was harder than we expected but we do not regret a moment.
    Trekking and Hiking
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    18-99 yrs
    Operated in
    english
    Destinations
    Siena, Lucca, San Miniato Alto
    Siena, Lucca, San Miniato Alto, Gambassi Terme, San Gimignano, Gracciano, Monteriggioni
    View Tour

    Page 14 of 477 Trips in Italy during May 2026 with 7,120 Reviews

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