My sister and I are planning a trip to Italy in November and will fly into Rome, 2 days, down to Sorrento, 3 days, Taormina, 3 days and then to Venice, 2 days and Milan, 1 day and home. It seems that we will spend a large part of the trip on trains, especially on the leg from Taormina to Venice, 12-16 hours(is that possible?) Any suggestions on cutting that down? Would it make more sense to rent a car in Naples and Drive to Venice?
I know we probably should remove at least one city from the trip, probably Sicily, but we may never make it there again. Help!

Even if you rent a car Taormina is a long way from Venice...

Also I believe that you must go to Naples to take the train for taormina, I may be wrong, I am not too familiar with the South .
If this is the case, according to trenitalia,from Naples to Taormina is a 6:36 minutes train ride.
Good luck, I understand that you really want to go to Sicily, but I dont know if is worth the long train ride..
The other option is to fly..

Yopu can fly on volareweb.com from Palermo or Catania to VCE.

Might be relevant flights on Alpi Eagles too.

Best wishes,

Rex

Book a sleeper on an overnight train to or from Sicily. There are several night trains which cross the Straits of Messina by ferry so you don't even have to get out of bed.

You could take an overnight ferry from Naples to Taormina and then use one of the discount airlines from Taormina or Palermo to Venice.

I'd drop Sicily unless you have some very substantial reason for going there.

Asking the question means you must already sense that the trip is too "far flung" and needs to be pared back so you can enjoy the other places.