Italy Tours in May 2026
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10 best Italy trips in May 2026
Compiled by

MelissaItaly travel expert at TourRadar
- Mamma Mia! Best of Italy
- Sicilian Secrets - Tour of Sicily 6 days
- Iconic Italian Cities
- The Italian Dream
- Italy : Cities and Lakes W/top sightseeing & train rides 4 Star
- Standard 8 nights Italy
- Sicilian Secrets - Mini Tour of Sicily 5 days
- Ultimate Italian Adventure: Venice, Rome, and Amalfi Coast Experience
- Best of Italy (13 destinations)
- Highlights of Italy : Colosseum, Cinque Terra, Gondola
Mamma Mia! Best of Italy
50 Reviews by TourRadar travelers“We visited many amazing places and, in comparison to other tours I've been on, the accommodation and food provided on this tour were generally superior.”
Axel, traveled in January
Duration 10 days Destinations Rome, Pompei, Sorrento, Capri, Assisi, Siena, Florence, Bologna, Venice Age Range Ages 6+ Operated in English, Spanish Operator Eskapas May departure dates
See All Departure Dates4 May, 2026 10+ spaces left 6 May, 2026 10+ spaces left From $5,752
10% Off- NZ$5,177You save $575
Sicilian Secrets - Tour of Sicily 6 days
28 Reviews by TourRadar travelers“The Sicilian countryside was beautiful as were the towns and sites visited – Noto, Valley of the Temples, Monreale and Palatine Palace.”
Philip, traveled in May
Duration 6 days Destinations Catania, Syracuse, Noto, Ragusa, Modica, Piazza Armerina, Agrigento, Marsala, Monreale, Palermo Age Range All Ages Welcome Operated in English, Italian, Spanish Operator Dimensione Sicilia - Dimsi Incoming Operator Srl May departure dates
See All Departure Dates2 May, 2026 10 spaces left 9 May, 2026 10 spaces left From $2,445
20% Off- NZ$1,956You save $489
Iconic Italian Cities
1 Review by TourRadar travelers“The tour was good with some good selections of places to visit.”
Patrick, traveled in May
Duration 9 days Destinations Milan, Lake Como, Venice, Florence, Rome Age Range All Ages Welcome Operator Wonderful Holidays UK May departure dates
See All Departure Dates3 May, 2026 10 spaces left 13 May, 2026 10 spaces left From $3,591
10% Off- NZ$3,232You save $359
The Italian Dream
183 Reviews by TourRadar travelers“The hotels were all good. The airport transfers were well done.”
John, traveled in June
Duration 8 days Destinations Rome, Assisi, Siena, Florence, Bologna, Venice, Montepulciano Age Range All Ages Welcome Operator Wingbuddy May departure dates
See All Departure Dates1 May, 2026 10+ spaces left 3 May, 2026 10+ spaces left From
10% Off- NZ$2,671
Italy : Cities and Lakes W/top sightseeing & train rides 4 Star
2 Reviews by TourRadar travelers“Price was reasonable, customer service was the BEST, staff were very responsive to all questions.”
Marsha, traveled in December
Duration 9 days Destinations Milan, Lake Como, Venice, Florence, Rome Age Range All Ages Welcome Operator Wanderful Holidays LLC May departure dates
See All Departure Dates3 May, 2026 10 spaces left 30 May, 2026 10 spaces left From $3,720
10% Off- NZ$3,348You save $372
Standard 8 nights Italy
2 Reviews by TourRadar travelers“Good itinerary for a quick visit to top 4 Cities in Italy. Good for first timers or those too busy to plan their trip.”
Debashis, traveled in May
Duration 9 days Destinations Milan, Lake Como, Venice, Florence, Rome Age Range All Ages Welcome Operator Wanderful Holidays LLC May departure dates
See All Departure Dates17 May, 2026 10 spaces left 30 May, 2026 10 spaces left From $3,213
10% Off- NZ$2,891You save $321
Sicilian Secrets - Mini Tour of Sicily 5 days
22 Reviews by TourRadar travelers“The overall tour in Sicilia is so impressive. Overall the agenda every day was well managed and we really enjoy the whole trip.”
LING, traveled in July
Duration 5 days Destinations Palermo, Monreale, Cefalu, Catania, Mount Etna, Taormina Age Range All Ages Welcome Operated in English, Italian, Spanish Operator Dimensione Sicilia - Dimsi Incoming Operator Srl May departure dates
See All Departure Dates5 May, 2026 10 spaces left 12 May, 2026 10 spaces left From $2,043
20% Off- NZ$1,635You save $409
Duration 10 days Destinations Venice, Rome, Sorrento, Naples Age Range All Ages Welcome Operator Wonderful Holidays UK May departure dates
See All Departure Dates1 May, 2026 10 spaces left 5 May, 2026 10 spaces left From $3,366
10% Off- NZ$3,029You save $337
Best of Italy (13 destinations)
16 Reviews by TourRadar travelers“This trip was for the adventurous and with a medium level of fitness. The tour guide gave us the knowledge and guidance to feel comfortable.”
Deborah, traveled in April
Duration 14 days Destinations Rome, Florence, Lucca, Pisa, La Spezia, Cinque Terre, Portofino, Asti, Milan, ComoSee all destinations Age Range Ages 15+ Operator Intrepid Travel May departure dates
See All Departure Dates2 May, 2026 7 spaces left 4 May, 2026 10+ spaces left From $7,340
20% Off- NZ$5,872You save $1,468
Duration 8 days Destinations Rome, Florence, Cinque Terre, Venice Age Range All Ages Welcome Operator Wonderful Holidays UK May departure dates
See All Departure Dates1 May, 2026 10 spaces left 5 May, 2026 10 spaces left From $3,366
4% Off- NZ$3,231You save $135
What people love about Italy Tours in May
- The Italian Dream
Good Morning Wingbuddy, I just wanted to say, Thankyou so much for all your help in making this a wonderful trip. My daughter and I had the most wonderful time. Our flights were wonderful with little delays between airports and our Hotel was so beautiful, clean and helpful. Our tours were awesome as well. I would recommend your company to to anyone. Thankyou again, Sincerely Izy B
- Sicilian Secrets - Mini Tour of Sicily 5 days
Tour was very good organized. Tour guide Placido was excellent. The only problems were hotels. May be it would be the good idea to have options to pay extra and stay in better hotels or even rooms.
- Northern Italy Tour
Amazing trip ! We loved both Spain and Portgual. Every location had its own unique beauty. Since it was such a huge itinerary, we felt like we couldn't have created a itinerary nearly as good as this one, furthermore our guides made this experience even better. Thanks to them we learnt a lot. Our hotels were boutique, clean and well located. Overall we strongly recommend this trip.
What our customers ask about Italy Tours in May 2026
What is the weather like in different regions of Italy during May?
Each region of Italy presents distinct temperatures during May. Northern cities like Milan and Venice see daily averages of 68-75°F (20-24°C). Central destinations including Rome and Florence maintain pleasant temperatures of 70-77°F (21-25°C). The southern regions such as the Amalfi Coast warm up to 75-82°F (24-28°C). A TourRadar reviewer notes "May was the perfect month to visit - warm enough for comfortable sightseeing but not too hot for walking tours in Rome and Florence."
Which regions in Italy are best to visit in May?
The Amalfi Coast and Sicily offer excellent conditions in May before summer tourists arrive. The mild weather suits hiking on coastal paths including the Path of the Gods while Mount Etna provides clear views. Rome and Florence welcome visitors with ideal walking weather. Hotels like Taormina's Ariston and Palermo's Garibaldi serve as comfortable bases with springtime vistas. One TourRadar review confirms "the views were breathtaking with perfect visibility."
What are the must-see festivals and events in Italy during May?
Cultural celebrations fill the May calendar across Italy. Visitors can experience the medieval Calendimaggio Festival in Assisi watch the Giro d'Italia cycling race or join local food festivals celebrating spring harvests. Sicily's Noto hosts the vibrant Infiorata flower festival. According to a TourRadar traveler "experiencing the local May festivals really added an authentic cultural element to our tour."
Are water activities possible in Italy during May?
The coastal waters become inviting in May as temperatures reach 19°C (66°F) around the Amalfi Coast and Capri. Regular boat services resume to attractions like Capri's Blue Grotto and coastal excursions begin their seasonal schedules. Beachfront properties such as the Michelangelo in Sorrento provide easy water access. A TourRadar guest shared: "Our boat trip to Capri in May was perfect - warm enough to swim but not too hot for exploring the island."
What is the average cost of tours in Italy during May?
Eight-day tours in May typically cost between 2500-4600 USD depending on accommodation choices and included activities. Sicily small group experiences average 2800 USD per person while Amalfi Coast tours start around 2200 USD. Standard packages include stays at hotels like Ariston or Garibaldi daily breakfast select meals and expert-led excursions.
Are there any flower or garden attractions particularly beautiful in May?
Gardens reach peak beauty in May across Italy. Lake Como's Villa Carlotta Florence's Boboli Gardens and Rome's Vatican Gardens display rich spring colors. Florence's Iris Garden showcases its namesake flowers in full bloom. A TourRadar visitor observed "The gardens at Villa Carlotta were absolutely stunning in May with all the flowers in full bloom."
What makes May a good time to visit Italy's Amalfi Coast?
May brings optimal conditions to the Amalfi Coast with temperatures ranging from 20-25°C (68-77°F). Pink bougainvillea decorates Positano's terraced landscape while hikers enjoy the Path of the Gods under clear skies. Properties like Sorrento's Hotel Michelangelo and Chianti's Villa Pitiana enhance the spring experience. As noted by a TourRadar guest: "April/May was the perfect time to go and we had a good experience with all of the accommodations transportation and excursions."