My husband and I are going to Italy mid to end of May - flying in and out from Milan with 15 full days. We were originally going to Dolomites but due to poor planning we did not know it's not best to go end of May. I originally wanted to spend 5-6 days in Sicily to enjoy the beach and sun but I think that is not enough and should just focus on Northern Italy for this trip. We plan return maybe next year or 2028 to hit Rome, Amalfi, Capri, and Sicily.
With that said, need your help on how feasible this itinerary is, open to any feedback and changes!
Day 1 - En Route - Fly to Milan
Day 2 - Milan to Lake Como (land Milan at 6:30pm)
Day 3 - Lake Como
Day 4 - Lake Como
Day 5 - Verona
Day 6 - Venice
Day 7 - Murano and Burano
Day 8 - Florence
Day 9 - Florence
Day 10 - Florence to Tuscany Vineyard (pick up rental car)
Day 11 - Tuscany (just enjoying the rolling hills, Agriturismo, and more vineyards?)
Day 12 - Tuscany ^
Day 13 - Island of Elba (drive to Piombino and take ferry)
Day 14 - Island of Elba
Day 15 - Cinque Terre
Day 16 - Cinque Terre
Day 17 - Milan
Day 18 - Milan (fly out at noon)