Closest DAC to Vinyl Sound?

I love my vinyl, but sometimes it's a pain to keep flipping sides. I also have a lot of digital music (WAV, FLAC and MP3) that doesn't sound half bad through my Soundblaster X FI Titanium Fatality. But I'm wondering, is there a better way to enjoy digital? How would an external DAC stack up? Can anyone recommend a DAC that has that analog sound, or is it wishful thinking? Associated equipment includes Sound Valves VTP 101, Aragon 2004 and Large Advent Speakers. I also have an Adcom GCD 750 cd player that can accept a coax input.