Always use a compressor. I use it on MTB tires meaning 2.4"-2.6". Perhaps on skinny road tires it is doable with a pump.
I tried the standard Schrader-Presta adapters,
but got tired of threading and unthreading.
Then I picked up this, and found it more convenient.
I also considered buying a regular Presta valve/hose and mounting it on a compressor hose,
Compressors are also great for blowing away debris from cassettes, disc brakes, etc