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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 6,700 verified traveler experiences.

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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
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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 470 results
    Via Francigena: Aosta To Ivrea - May 2026

    Via Francigena: Aosta to Ivrea - May 2026

    5
    Fourth leg of our Camino. As always, very well organised - hotels, transfers, restaurant suggestions were all great. Stunning walking and scenery
    Walking tours
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    18-99 yrs
    Operated in
    english
    Destinations
    Turin, Ivrea, Aosta Valley, Aost
    Turin, Ivrea, Aosta Valley, Aosta, Nus, Saint Vincent, Verres, Pont-Saint-Martin
    View Tour
    Portofino And The Cinque Terre - May 2026

    Portofino and the Cinque Terre - May 2026

    5
    Great scenic walking with demanding ascents and descents but comfortably within the capability of a walker used to the Fells. The organisation was excellent and everything worked seamlessly. The hotels were all good although the quality of the restaurants in the villages was mixed with good and bad experiences from what was recommended. A great week.
    Walking tours
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    18-99 yrs
    Operated in
    english
    Destinations
    Cinque Terre and Liguria, Liguri
    Cinque Terre and Liguria, Liguria, Bonassola, Genoa
    View Tour
    A Taste Of Tuscany - Hilltop Towns And Vineyards - May 2026

    A Taste of Tuscany - Hilltop Towns and Vineyards - May 2026

    4.8
    Trip was excellent. Tour Guide, Gus, was fantastic, very knowledgeable, great communicator, and made sure all of our needs were met. Food and wine tour could not have been better. Never really liked many wines but the tastings proved me wrong. The agricultural farms were great and the food fresh and abundant. Villages were quaint. Castle was very interesting - 34 generations living in it and continuously running a vineyard and producing wine since 1141 is unbelievable! Looking into another food tour in another country. Gave accommodations less rating because hotels were in old buildings and they made due with space available: 1) First 2 nights in Hotel Bologna, the room was very, very small and had 2 twin beds aligned in tandem against one wall - would not have fit any other way, 2) Hotel Le Cisterna, last 3 nights, walls were so thin we could hear every word people next door said.
    Wine tasting toursFood tours
    Tour Type
    Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
    Accommodation
    Hotel
    Age Range
    16-99 yrs
    Operated in
    english
    Destinations
    Pisa
    Pisa
    View Tour

    Combine Italy in May with Nearby Countries for an Unforgettable Trip

    See tours with itineraries going through multiple countries, including Italy

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    Alternatively, explore tours that are exclusively just France and Italy.

    Sardinia Family Cycle Adventure - May 2026

    Sardinia Family Cycle Adventure - May 2026

    5
    We had a wonderful time on this cycling trip in Sardinia! It was a great route with lots to places to stop along the way. So much good food, and all the accommodation was wonderful. Some of the roads were a bit busy for my liking, not sure if I would be comfortable taking children on those roads but for adults it was fine. A very enjoyable week- a highlight of our month in Italy!
    Bicycle tours
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    18-99 yrs
    Operated in
    english
    Destinations
    Sardinia, Pula, Sant'Antioco, Sa
    Sardinia, Pula, Sant'Antioco, Sant Anna Arresi, Chia
    View Tour
    Treasures Of Rome And Amalfi Coast - May 2026

    Treasures of Rome and Amalfi Coast - May 2026

    5
    Rome’s history and the Amalfi Coast’s beauty? A perfect combo! From the Colosseum to Positano’s breathtaking cliffs, this trip was straight out of a postcard
    City sightseeing
    Tour Type
    Independent TourTypically a private tour undertaken by one or two travelers
    Accommodation
    Hotel, Villa
    Age Range
    8-99 yrs
    Operated in
    English
    Destinations
    Rome, Naples, Pompeii, Amalfi, Capri
    Rome, Naples, Pompeii, Amalfi, Capri
    View Tour
    Classic Amalfi Coast - 11 Days - May 2026

    Classic Amalfi Coast - 11 Days - May 2026

    4.6
    Very well organised trip. Logistics were excellent, accommodation was comfortable and central to all amenities of the towns. Hike maps and notes were extremely detailed. I would highly recommend them and am considering another trip in the near future.
    Trekking and Hiking
    Tour Type
    Private Tour
    Accommodation
    Hotel, Villa
    Age Range
    18-99 yrs
    Operated in
    english
    Destinations
    Amalfi Coast & Campania, Amalfi
    Amalfi Coast & Campania, Amalfi, Sorrento, Naples, Praiano, Positano
    View Tour
    St Francis Way: Rieti To Rome - May 2026

    St Francis Way: Rieti to Rome - May 2026

    4
    This was a wonderful walk through the Italian landscape following quiet trails peppered with villages and ancient hilltop towns. The walking provides a sense of achievement with occasional long days and steep rocky trails.
    Trekking and Hiking
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    18-99 yrs
    Operated in
    english
    Destinations
    Rome, Rieti, Poggio San Lorenzo
    Rome, Rieti, Poggio San Lorenzo, Scandriglia, Nerola, Sabina, Monterotondo
    View Tour
    Rome, Florence & Venice - 8 Days - May 2026

    Rome, Florence & Venice - 8 days - May 2026

    4
    Dreaming of Italy’s classic wonders? The “Rome, Florence & Venice – 8 Days” sightseeing tour is perfectly tailored for experienced travelers and seniors seeking a comfortable yet enriching exploration of central Italy. Over eight days, travel by coach through Rome, Florence, and Venice, uncovering Renaissance architecture, medieval towns, and vibrant city life. Enjoy guided walks through Rome, skip the line to marvel at St Peter’s Basilica and the Sistine Chapel, and lose yourself in Florence’s artistic treasures. Visit Siena’s medieval streets, savor Montepulciano’s Tuscan charm, and take in Bologna’s lively ambiance. In Venice, wander romantic canals and discover hidden gems with an expert guide. This trip’s unique selling point is its comprehensive itinerary: it covers all the must-see sights and hidden corners, with expert commentary, included accommodations, and seamless transport—making it the ideal tour package for those who want to experience Italy’s highlights in comfort and style.
    Sightseeing Tours
    Tour Type
    Group Tour
    Accommodation
    Hotel
    Age Range
    18-80 yrs
    Operated in
    english
    Destinations
    Rome, Florence, Venice
    Rome, Florence, Venice
    View Tour
    Florence To Rome By Bike - May 2026

    Florence to Rome by Bike - May 2026

    5
    Wonderful trip. It was amazing to be able to travel from one hill town to another, each one so different from the others. Highlights of our trip included an art exhibit in Perugia on how medieval artists perceived nature - absolutely beautiful and we had the place to ourselves, quite a contrast to the crowds at the Uffizi; staying in a 14th century pilgrim guest house in Assisi; walking out to the aqueduct bridge in Spoleto; hearing all the bells in Narni suddenly start ringing when the new Pope was elected and running outside along with everyone else to find out what had happened; and, my husband would say, the wild boar stew he ate that evening at a restaurant in the square. Logistics were well organized and the routes well planned. It was a challenging route, however, with many steep climbs. We were glad we reserved e-bikes. There were also a number of places with poorly maintained roads, quite a bit of springtime road construction, and some areas where the route took roads with heavy traffic. Italian drivers were quite considerate, though. We had a great time and were sad to go home. We could have stayed in each town longer, and will hopefully return to Italy soon.
    Bicycle tours
    Tour Type
    Private Tour
    Accommodation
    Hotel
    Age Range
    18-99 yrs
    Operated in
    english
    Destinations
    Rome, Florence, Trasimeno Lake
    Rome, Florence, Trasimeno Lake, Perugia, Assisi, Clitunno, Narni
    View Tour
    Private Tour Of Sicily From Palermo - May 2026

    Private Tour of Sicily from Palermo - May 2026

    4.8
    This is our first private tour and I must say it met all our expectations. Our driver/guide Carlo took very good care of us, told us informative and amusing stories along the way and took us to wonderful restaurants. He made sure all our needs our taken cared of. In Sicily especially I think the private tour is a big advantage as there are many places where only small vehicles can go through. We made the right decision in choosing this tour.
    City sightseeing
    Tour Type
    Private Tour
    Accommodation
    Hotel, Villa
    Age Range
    20-99 yrs
    Operated in
    english
    Destinations
    Palermo, Catania, Taormina, Sici
    Palermo, Catania, Taormina, Sicily, Agrigento, Marsala, Monreale
    View Tour

    Page 17 of 470 Trips in Italy during May 2026 with 6,819 Reviews

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