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

MelissaItaly travel expert at TourRadar
- 8-day Best of Italy: Rome, Florence & Venice
- Italian Discovery
- 5-day Best of Italy: Rome, Florence & Venice
- Mamma Mia! Best of Italy
- The Italian Dream
- Sicilian Secrets - Tour of Sicily 6 days
- Sicilian Secrets - Mini Tour of Sicily 5 days
- Sicilian Secrets – Tour of Sicily & Aeolian Islands
- Sicilian Secrets - Tour of Sicily 10 days from Catania
- Best of Italy (26 destinations)
8-day Best of Italy: Rome, Florence & Venice
32 Reviews by TourRadar travelers“It is worth the price we paid. I had a great experience with this tour.”
Ilaine, traveled in February
Duration 8 days Destinations Rome, Assisi, Siena, Florence, Bologna, Venice, Montepulciano Age Range Ages 18+ Operator Carrani Tours May departure dates
See All Departure Dates1 May, 2026 10+ spaces left 3 May, 2026 10+ spaces left From
- NZ$2,612
Italian Discovery
123 Reviews by TourRadar travelers“Excellent tour and our tour guide Niki was FANTASTIC! We loved that Niki stuck with us through the Sorrento, Naples, Capri part of our tour package as well!”
Mark, traveled in October
Duration 11 days Destinations Rome, Assisi, Siena, Florence, Bologna, Venice, Montepulciano, Pompeii, Sorrento, Capri Age Range Ages 6+ Operated in English, Spanish Operator Eskapas May departure dates
See All Departure Dates3 May, 2026 10+ spaces left 10 May, 2026 10+ spaces left From $5,216
10% Off- NZ$4,694You save $522
5-day Best of Italy: Rome, Florence & Venice
23 Reviews by TourRadar travelers“Well organized with a lot of wonderful experiences.”
Elin, traveled in July
Duration 5 days Destinations Rome, Assisi, Siena, Florence, Bologna, Venice, Montepulciano Age Range All Ages Welcome Operator Carrani Tours May departure dates
See All Departure Dates2 May, 2026 10+ spaces left 4 May, 2026 10+ spaces left From
10% Off- NZ$1,723
Mamma Mia! Best of Italy
50 Reviews by TourRadar travelers“I enjoyed the tour. It hit all major cities and the tour guides were amazing.”
Kahli, traveled in September
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 $5,721
10% Off- NZ$5,148You save $572
The Italian Dream
183 Reviews by TourRadar travelers“Both professional and friendly, she made the trip a huge success for us.”
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$2,657
Sicilian Secrets - Tour of Sicily 6 days
31 Reviews by TourRadar travelers“The staff were your backbone in keeping the tour going & making it memorable.”
Garry, traveled in September
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 $2,290
10% Off- NZ$2,061You save $229
Sicilian Secrets - Mini Tour of Sicily 5 days
22 Reviews by TourRadar travelers“It's the perfect itinerary to discover the beauties of Western Sicily. All the facilities were great.”
Ylenia, traveled in April
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 $1,914
10% Off- NZ$1,722You save $191
Sicilian Secrets – Tour of Sicily & Aeolian Islands
5 Reviews by TourRadar travelers“Excellent hotels and trip. Times kept to by everyone. Bit of confusion over one tour on Lipari but it was all cleared up quickly.”
Laura, traveled in September
Duration 9 days Destinations Palermo, Monreale, Cefalu, Catania, Mount Etna, Taormina, Lipari, Salina, Panarea Island, Stromboli 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
10% Off- NZ$4,134
Sicilian Secrets - Tour of Sicily 10 days from Catania
7 Reviews by TourRadar travelers“We had the opportunity to enjoy the best of Sicily in 10 days. Hotels and meals were good and Taormina is not to be missed.”
Rivadavia, traveled in June
Duration 10 days Destinations Catania, Syracuse, Noto, Ragusa, Modica, Piazza Armerina, Agrigento, Marsala, Monreale, PalermoSee all destinations 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 $4,453
10% Off- NZ$4,008You save $445
Best of Italy (26 destinations)
17 Reviews by TourRadar travelers“He was able to accommodate most of the wishes of our group by giving options whereby people could still have personal choices.”
Bessie, traveled in August
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
10% Off- NZ$6,190
What people love about Italy Tours in May
- 8-day Best of Italy: Rome, Florence & Venice
There were many amazing highlights in this trip. The guide was organized, with knowledge of the different places and with a good domain of different languages, but I felt he was not patient with the group and not always was keeping up that everybody was already in the meeting point before leaving the place. The bus that transported us was comfortable and clean and the bus-driver was friendly.
- Italian Discovery
We had an amazing time! The accommodations were immaculate, the bus journeys went without a hitch, and Rocio, our tour guide, was kind and helpful during the trip! The meals were fine.The places we went were ideal and historically significant! There was a lot of walking, and our guide made sure to check on us frequently. The quality / price ratio is excellent! If this is your first time visiting Italy, we highly recommend this tour!
- 5-day Best of Italy: Rome, Florence & Venice
We had a great trip! Saw places I would have never seen (names were new to me) and they didn’t disappoint! Carlos & Stefano were great and we definitely recommend
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."