Wanting to try flying

I have always admired the beauty of fly fishing. My grandfather was fly fisherman and I thought I would honor him by giving it a shot.
Since I am new to it i haven’t a clue on what reel and rod to get or what tides to fish and where. Any help is greatly appreciated.
I will spend up to $800 on a fly combo.
Also can you fly in the winter?Where?

21’ Sea Pro Bay, Yellow
225 Mercury Verado
Named: Faith & Grace after my wife and daughter