Critique my Itinerary

See if this view helps any:

Daytime Location Overnight

4:00 Arrive at FCO Rome

Rome Day 1 Rome

Rome Day 2 Rome

Rome Day 3 Rome

Pompeii, Vesuvius Sorrento

Sorrento, Amalfi Coast Sorrento

Capri Sorrento

Travel to Sora Italy Farm Stay

Farm Italy Farm Stay

Travel and Orvieto Siena

Siena, surrounding Siena

Florence Florence

Florence Florence

Florence Florence

Travel to Pisa, CT Cinque Terre

Cinque Terre Cinque Terre

Cinque Terre Overnight Train

Venice Venice

Venice Venice

Lake Como Lake Como

Lake Como Milan

I know everyone will tell you it's too compressed. As long as you are an energetic person, it will be okay.

Plan on returning to Rome, there is so much to see you'll need a return trip (throw a coin in the Trevi fountain).

Florence is a rushed two days. The lodging is expensive and not great so you'll be glad to move on. Reserve ahead for the two big museums so you don't miss the must sees.

Orvieto and Siena are two of the best small cities in Tuscany/Umbria.

San Gimignano is a touristy but great small medieval town. If you get a chance, it's worth a stop.

Plan for two hours max at Pisa. Take the obligatory photo holding up the tower, see the tower, cathedral and baptistry.

Lucca has an 18th century wall that is turned into a nice park. Overall it wasn't worth stopping.

Orvieto is good for one night. An extra night in either Venice or Lake Como would be good.