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

MelissaItaly travel expert at TourRadar
- 5-day Best of Italy: Rome, Florence & Venice
- The Italian Dream
- 8-day Best of Italy: Rome, Florence & Venice
- Sicilian Secrets - Tour of Sicily 6 days
- Sicilian Secrets - Mini Tour of Sicily 5 days
- Sicilian Secrets - Tour of Sicily 10 days from Catania
- Mamma Mia! Best of Italy
- Southern Italy
- Sicilian Secrets – Tour of Sicily & Aeolian Islands
- Best of Italy (13 destinations)
- 5-day Best of Italy: Rome, Florence & Venice24 Reviews by TourRadar travelers- “Good overall tour.” - Marcos, traveled in October 
 No departure dates available- Duration - 5 days - Destinations - Rome, Assisi, Siena, Florence, Bologna, Venice, Montepulciano - Age Range - All Ages Welcome - Operator - Carrani Tours 
- The Italian Dream184 Reviews by TourRadar travelers- “The hotels were very nice close to city centers and meals were flavorful delights. I loved the tuscany part of the tour.” - DLawrence, traveled in September - Duration - 8 days - Destinations - Rome, Assisi, Siena, Florence, Bologna, Venice, Montepulciano - Age Range - All Ages Welcome - Operator - Wingbuddy - May departure dates 
 See All Departure Dates- 1 May, 2026 - 10+ spaces left - 3 May, 2026 - 10+ spaces left - From 
- NZ$2,748
 
- 8-day Best of Italy: Rome, Florence & Venice37 Reviews by TourRadar travelers- “I absolutely loved how informative and helpful the tour was.” - Sarah, traveled in April - Duration - 8 days - Destinations - Rome, Assisi, Siena, Florence, Bologna, Venice, Montepulciano - Age Range - Ages 18+ - Operator - Carrani Tours - May departure dates 
 See All Departure Dates- 1 May, 2026 - 10+ spaces left - 3 May, 2026 - 10+ spaces left - From 
- NZ$2,671
 
- Sicilian Secrets - Tour of Sicily 6 days31 Reviews by TourRadar travelers- “The wine tour was fun. The sights we were taken to were nice to see.” - Sammy, traveled in April - 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 Dates- 2 May, 2026 - 10 spaces left - 9 May, 2026 - 10 spaces left - From 
- NZ$2,536
 
- Sicilian Secrets - Mini Tour of Sicily 5 days23 Reviews by TourRadar travelers- “Everything was very well organised, we appreciated Hotel's choice and especially food!” - Ada, traveled in August - 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 Dates- 5 May, 2026 - 10 spaces left - 12 May, 2026 - 10 spaces left - From 
- NZ$2,113
 
- Sicilian Secrets - Tour of Sicily 10 days from Catania7 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 Dates- 2 May, 2026 - 10 spaces left - 9 May, 2026 - 8 spaces left - From 
- NZ$4,931
 
- Mamma Mia! Best of Italy52 Reviews by TourRadar travelers- “Italy was a beatiful country and thanks to the very detailed and organized itineary, we felt like we got the best potential tour possible for 8 days.” - Abby, traveled in August - Duration - 10 days - Destinations - Rome, Pompei, Sorrento, Capri, Assisi, Siena, Florence, Bologna, Venice - Age Range - Ages 6+ - Operator - Eskapas - May departure dates 
 See All Departure Dates- 4 May, 2026 - 10+ spaces left - 6 May, 2026 - 10+ spaces left - From $5,918 10% Off
- NZ$5,326You save $592
 
- Southern Italy50 Reviews by TourRadar travelers- “The hotel locations were very good, and the trip was quite well-planned.” - Aaliyah, traveled in June - Duration - 11 days - Destinations - Rome, Sorrento, Capri, Pompeii, Palermo, Erice, Agrigento, Ragusa, Noto, SyracuseSee all destinations - Age Range - Ages 6+ - Operator - Eskapas - May departure dates 
 See All Departure Dates- 3 May, 2026 - 10+ spaces left - 10 May, 2026 - 10+ spaces left - From $7,745 3% Off
- NZ$7,513You save $232
 
- Sicilian Secrets – Tour of Sicily & Aeolian Islands6 Reviews by TourRadar travelers- “The architecture & history was amazing! For the cost, I think the tour was good value for money.” - Shiree, traveled in October - Duration - 9 days - Destinations - Palermo, Monreale, Cefalu, Catania, Mount Etna, Taormina, Lipari, Salina, Panarea Island, Stromboli - Age Range - All Ages Welcome - Operator - Dimensione Sicilia - Dimsi Incoming Operator Srl - May departure dates 
 See All Departure Dates- 5 May, 2026 - 10 spaces left - 12 May, 2026 - 10 spaces left - From 3% Off
- NZ$4,034
 
- Best of Italy (13 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 
 No departure dates available- 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 
What people love about Italy Tours in May
- 5-day Best of Italy: Rome, Florence & VeniceGood overall tour. Thanks. 
- 8-day Best of Italy: Rome, Florence & VeniceOverall tour was great. Carlos, the tour guide was excellent. Gives clear and descriptive explanations of tour sights and places. The local tour guides in Florence, Pisa, Venice and Rome were very good as well. They really know their trade and were very caring with the group. 
- The Italian DreamItinerary excellent. Hotels good or very good. Tour leader/guide very good, but sometimes talked too much. A lot of walking, more than we older folks expected. Overall excellent value. 
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." 




















