Hey there, I would absolutely love some feedback about this itinerary!
For some context, we are fairly active travelers and aren't opposed to using short road trips to see and explore places. I should also note this will be our first time in Italy, so seeing Venice is important to us. Based on what we're reading online, we're considering consolidating May 13 - 15 into having Siena as a base and planning day trips around it.
Itinerary: May 4 - Arrive to Venice in the evening
May 5 - Full day in Venice
May 6 - Full day in Venice
May 7 - Leave early morning for Florence (train), mostly full day in Florence
May 8 - Full day in Florence
May 9 - Full day in Florence
May 10 - Day trip Pisa & Lucca - sleep Florence
May 11 - Leave for Cinque Terre early morning, mostly full day in Cinque Terre
May 12 - Cinque Terre full day
May 13 - Train to La Spezia to rent a car - drive to Siena
May 14 - Drive to Assisi
May 15 - Drive to Orvieto
May 16 - Train to Rome
May 17 - Rome
May 18 - Rome
May 19 - Travel day home