Join Date: Jun 2008
Location: Tampa, FL
Thanked 37 Times in 37 Posts
Rep Power: 9
I'm told that documentation makes entry into some foreign ports a little easier. My understanding, though, is that all of the countries in the Caribbean basin are pretty familiar with U.S. state registration of boats, and that (in this area, anyway) it really doesn't matter much whether your boat is documented or state registered.
My only personal experience with this is sailing a boat registered in Florida, and not documented, to the Bahamas. Clearing in was quick and easy, and they seemed quite familiar with the state registration papers that I had.