there is one way this possible, iv seen it done early on server 1. It may have been changed since. If a player has a map and gets in a boat and stays in it past 12 am server time, they can they claim guild benefits again and have a second map. Ive actually seen someone sail by themself, becuase they had a left past midnight and claimed a right.

No in terms of getting a second map super fast. Sam basic idea
Steal a map
sail
as soon as that sail is over or during that sail claim guild benefits have another map.