Making a wedding playlist... Need an app/program that will fade the songs without gaps!

Christ almighty, I haven't half left this until the last minute.

Does anyone know of any apps that will play a playlist from VLC or Media player that will fade the next song on the list in as opposed to having any gaps in between tunes?

This is a wedding gift for my little sister and I want it to go smoothly without having to stand at a laptop all night ensuring there are no awkward silences in between songs.

I'm quite new to Reddit so if there is a more appropriate sub reddit to post this in, please let me know.

Your help is greatly appreciated.