I am in Washington DC and I try to leave out of NJ or NY when I can, it's closer. I use Florida most times as you get more bang for your buck.

I lived in Germany, so visited Italy, but mostly driving.

When you travel for linger periods of time. The ships tend to overnight at a few ports, like they do in Bermuda. I like that pirt as it is a three day pirt from NY, NJ or Baltimore. Cheaper than staying at a hotel and flying in.