I have my Step-Dad's old Omega Seamaster, my Grandfather's old Fortis and my Dad's gold Hamilton. The Hamilton was a high school graduation gift he received in 1950. All three of those watches run perfectly.
I have my black Omega Seamaster Co-Ax, a Rolex Sea Dweller, a Breitling Avenger Seawolf, an Oris Williams F1 and an Omega Planet Ocean 45. I've got my eye on a Rolex Explorer II, but they can get a bit spendy. I also want to find an original Oris Carlos Coste. Aside from those, I also have Tissot, Eduoard Louzier
Here are some pics. I should probably photograph the collection...
The Planet Ocean:

The Oris:

The Breitling:

I also have a rather nice Edouard Lauzeires Park Avenue. It wasn't terribly expensive, but it's awfully classy looking:


My most prized watch, however, is the one I wore during Desert Storm. It's a Citizen, although I'm not sure of the model. I was deployed for just over ten months, and this watch was on my wrist every single day. I call it "The Watch That Won The War":
