Traveling to Italy in May 2026? We offer 500+ tours, trips and vacation packages to Italy in May 2026. Our Italy in May 2026 tour packages and trips have 7110+ customer reviews. All the Italy May 2026 tour packages and trips are carried out by hand-picked, qualified local and international Italy tour operators.
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
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A very pleasant and enjoyable holiday with great accommodation, views ,walks and guides.
Enrico our rep was fantastic. Friendly, funny and engaging. A brilliant ambassador for EXPLORE.
Would have no hesitation in going with them again. Thank you.
Walking toursCity sightseeing
Tour Type
Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
What a wonderful trip ! An exciting walking adventure with a wonderful guide, magnificent scenery , a great group of likeminded hikers and an awesome hotel
Trekking and Hiking
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
Niederdorf, Dolomites, Lago Di B
Niederdorf, Dolomites, Lago Di Braies, Alpe Nemes, Strudelkopf, Brunico, Tre Cime Di Lavaredo, Monte Piano
This tour is the BEST way to see all the infamous spots in Italy, plus local hidden gems, at a reasonable cost and if you are short on time (we had a school break time limitation). It covered everything! We budgeted for the add-ons, especially those with meals, but you could choose to have more free time if you wanted. The food was extraordinary, the bus was roomy and immaculately clean, our driver Antonello was superb, and our Travel Director Anneleis was amazing! She was so talented at integrating the tour highlights, guests, keeping it fun even in the rainy weather, knowledgeable, and able to troubleshoot anything to ensure we had the best experience of a lifetime!! I would love to go back and explore Southern Italy next. The hotels were elegant (only one was just "OK" only because it was in need of some renovations) and the service with our luggage, tipping, etc. was seamless. I highly recommend the Italian Intermezzo tour and Insight Vacations. Favoloso!
Our family of 5 adults recently went to Italy on a 9 day trip to Venice, Rome and Sorrento(Amalfi Coast) with private tours, fast train travel, door to door drivers, and great accommodations; which was all set up by Michael.
Michael was very responsive to my communications, very helpful with trip suggestions to make the trip better, and just overall a great travel planner! I was nervous at first, because I have never completely booked a vacation online without ever meeting the travel planner, but it all worked out great!
We were completely happy with everything about our trip, and will definitely reach out to Michael again when we travel to Italy! There were a couple of small issues that arose over the duration of the trip, but they were handled quickly and without further problem to us. So all was good.
Our private tour guides in Rome, Ornella; and Roberta in Pompeii were incredible. Our Venice tour guide, Cynthia, was awesome too, she did a great job! We did a full day 8 hr tour in Rome of the Colosseum and Vatican, and I would recommend splitting that to two half days if you have the time. It was awesome, but a bit much for one day!! Also, we had a full day Amalfi Coast tour by van, with great driver Antonio, which was supposed to go to Positano, Amalfi, & Ravello, but because the traffic is so bad on the roads, there wasn't time to make it to Ravello. So, I recommend either going by boat, which we hear is faster, or allow more time if you want to see all three villages.
Again, a great trip for the memory books! Thank you MIchael and all of the local operators who worked to make our trip such a success!!
Received excellent service and suggestions for a tour we planned for our son and daughter when they toured the Amalfi Coast in August. Hotels were all in great locations close to the action and all excellent 4 or 5 star. Would definitely use or recommend the tour operator to friends or family.
Countryside and village visits
Tour Type
Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
Pressed for time but eager to soak up the Amalfi Coast’s best? The Naples Express & Sorrento - Small-Group Tour is a 4-day sightseeing adventure perfect for families and travelers of all ages. Start in Rome and journey to Naples, where you’ll step back in time at the ruins of Pompeii. Set sail for a day trip to Capri’s idyllic shores, then relax in the charming town of Sorrento, with plenty of free time to explore at your own pace.
The tour includes accommodation, transport, and guided sightseeing, ensuring comfort and ease throughout. The unique selling point? A thoughtfully curated itinerary that captures southern Italy’s must-see highlights in just four days—ideal for travelers who want a rich Italian experience without the rush.
Sightseeing Tours
Tour Type
Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
Lace up your hiking boots and set your sights towards the spectacular Mediterranean horizon. This seven-day Premium walking and hiking trip on the Amalfi Coast features the best of the short hikes in the area, and is a nature-lover’s dream! Walk the crater rim of the Mount Vesuvius volcano, say Buongiorno to local farmers along the Pathway of the Gods, take in sweeping panoramic views from the Path of the Lemons, and catch a ferry to the glamorous island of Capri. Then, visit Pompeii to explore the preserved ruins and learn about the history of the area. Spend two nights in in a clifftop hotel, soak up sunsets, eat your weight in delicious Italian food (carbs, anyone?) and get active in one of the most beautiful parts of Italy, if not the world.
Trekking and Hiking
Tour Type
Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
Experience a grand sweep of Italy’s heritage on the 12-day “Irresistible Italy: Rome to Venice” tour, a journey that invites families and travelers of all ages to soak in the country’s timeless allure. Start with private transfers in Rome and delve into the city’s legendary sites, from the Colosseum to the Roman Forum. Sip Chianti in Tuscany, take a coach tour through Florence’s artistic heart, and enjoy the freedom of a 48-hour train card in the picturesque Cinque Terre. Glide along Lake Como’s waters and finish with a gondola ride in Venice, all while traveling effortlessly by high-speed trains. This trip’s unique advantage lies in its blend of guided tours and independent exploration, offering both structure and flexibility for an enriching Italian adventure.
Explorer
Tour Type
Private Tour
Accommodation
Hotel
Age Range
7-99 yrs
Operated in
english
Destinations
Rome, Florence, Venice, Colosseu
Rome, Florence, Venice, Colosseum, La Spezia, Cinque Terre, Milan, Lake Como
