Just picked up a trick by accident. Let's say you want to go North, but would be Beating Windward (-3). Instead, you can manually set a path and go Northwest a bit, then Northeast a bit, and zigzag your way to your destination. This way you will only be at -1 penalty and significantly cut down on sailing accidents, time spent, and encounter penalties.
ST2 Alpha - HuaWei P10 Plus, Build VKY-L09 184.108.40.2063(C654), EMUI 8.0.0, Android 7.0, res 2560×1440 [Not in use: ST2 Alpha - iPad 2(?), Model MC980C/A, OS Version 9.3.5 (13G36)]