Europe is full of low clearance bridges and many of the sailboats there have masts in 'tabernacles' that facilitate easy lowering and raising... there's even a week-long regatta somewhere in England where the racers have to do this several times a day!
Such setups are rare in North America, but certainly do-able.
1984 Fast/Nicholson 345 "FastForward"
".. there is much you could do at sea with common sense.. and very little you could do without it.."
Capt G E Ericson (from "The Cruel Sea" by Nicholas Monsarrat)