Milan to Palermo
 

I'm planning a January trip to Italy and want to go from Milan to Palermo. I'm planning on spending 2 days in Milan, 1 in Pisa, 2 in Naples and 2 in Sicily. I know it's kind of whirlwind but that's the way I like to travel....real power sightseeing. My dad was born in Sicily and I'd like to see his hometown of Cattolica near Agrigento.

Am I crazy?

You probably won't find too many people on this forum who will agree with your mode of travel. You are likely to do more moving around than sightseeing with your itinerary. Since you want to see Sicily and I think Sicily is a wonderful place to visit (but for a lot more than two days), why don't you fly from Pisa to Palermo and spend all of your available time in Sicily. It looks like it will be five days at the most - not nearly enough time - but it gives you a fighting chance to actually see something.

Do you already have your plane tickets? If not, why not fly into Pisa, spend a day there and go to Palermo the next day?

That isn't a trip I would want to take! WAY to much time in transit and WAY too little time to see anything. In my opinion, Sicily deserves at least 2 weeks even at a very fast pace. If you only have a few days and really want to see your father's hometown on this trip, do consider going straight to Sicily. Hope that helps!

With two days in Sicily, you want to go Cattolica Eraclea near Agrigento? There are three airports in Sicily: Palermo, Catania and Trapani (with limited flights). None of them is close to Agrigento. You'll have to take a bus to Agrigento, then a local bus (if there is one) to Cattolica Eraclea. With luck, you'll get there by late afternoon or early evening. If you manage to get a latish flight out, you'll have to leave quite early in the morning. Renting a car will save you *some* time.

Get real.

As a straightforward answer to your question: yes. This is not real power sightseeing, 1. because it's not real, as Zerlina said, 2. because it can't be sightseeing if you don't see any sights. Italy is not a country where rail stations are typically the biggest sight in town.