I have surveyed my 2003 H356 and with light, VHF antenna, wind instrument and I am 58.5 feet above the water line. My specs say 55'3. What that actually is measured to is from water to the flat end at the top of the mast. You need to add the light - can add 12 to 14 inches and your wind device. These are both expensive items to replace. The VHF antenna can be deflected by the bridge structure. On mine, it is 3.25 feet iabove the flat part of the mast and just over 2 feet above the light. I have scraped my antenna a number of times on bridges on Kentucky Lake. I know exactly how much I can push it because I have very accurately measured all these heights. It is about $2500 to replace all the stuff on top of the mast. I know that for a fact! It will also vary some based on loading and waves. I have never been sure about whether the published clearance is to the light that sticks down below the structure or the structure itself. I have been officially told it is to low steel, and the light could be below that.
Another interesting element is the type of bridge. Arch bridges are measured from the low steel near the support and offer more clearance in the middle. Flat bridges such as a typical railroad bridge generally have X brace horizontal stiffeners under the roadway. If you know you are going to scrape the antenna without hitting anything else, then try to go through in the center of the X. There are beams on both outside edges that will hit your antenna, but once clear it will spring back up into the void created by the interior x beams. You will then make contact with the center and when exiting on the other side. If you don't go through in this manner you will scrape along and make more contact and can create a spinning antenna. The spinning and whipping antenna can get your windex and might contact and ruin your wind machine. Best advice is know exactly how tall you are, monitor tide or water level from "normal pool" or Mean High Water and go through with NO WAVES. If in doubt be very careful. Also consider some weight on the end of your boom, swing it out and heel you boat 10 degrees. This will pick up several inches of additional clearance.