Pshhhhh the Black Pearl pwns all. Put some steel on that and arm it with modern weapons and you got yourself a killing machine. An undead crew wouldn't hurt either.
Titanic. That was one beautiful boat, even if it was a flawed design.
If you were to throw in modern safety precautions it's really not that bad of a design.
This is my favorite real life design.
The cabin is sort of on this gyroscope like mount so the part that touches the water is what moves and that movement isn't transferred to the cabin. This way you don't feel the rocking motion of the water and you always remain level.
Favorite fictional ship I will give it to the Enterprise-D from Start Trek Next Generation.
Have to agree there. There were a few different types but all were perfect for their purpose (troup/merchandise transport). They were light and could sail on shallow waters, land on shores during a raid, their back/front almost-symmetry allowed them to sail in both directions :P and they were sturdy and yet flexible. And I simply like their design, they're quite esthetic.
The Bismarck. Biggest battleship ever created. The glory days of ship building, in my opinion. Unfortunately anti-ship cruise missiles have rendered such large designs obsolete.