Any advice on doing the same with audio cassettes? I have dozens of books on tape I'd like to move over to my old MacBook.
Given the vast number of books-on-tape sets sold in the last years of the 20th century, this is an excellent question. The audio quality of a cassette tape is far worse than that of a CD, but you don’t need pristine quality for an audiobook.
Regrettably, turning a tape-based audiobook into something you can listen to on your computer or mobile device is far more laborious than ripping an audio CD. Not only are the hardware connections more complicated, but you have to record in real time—start the tape playing and record it as it plays. Quite honestly, for an eight-hour audiobook I’d rather just pay Audible.com or the iTunes Store for the thing in digital form. But if the book’s not available digitally or you’re just dead-set on doing it, it goes like this.
First, unearth your old cassette deck. Purchase an RCA-to-3.5mm audio cable (Monoprice link), connect the RCA ends to the cassette player’s outputs and the 3.5mm plug to your Mac’s audio input port. That takes care of your hardware hookup.
You’ll now need an audio editing application. The free open-source Audacity is a popular application with the cheapskate crowd because it packs a punch, but it may be one of the clumsiest interfaces I’ve ever encountered. If you know your way around GarageBand I’d suggest using it instead if you have a copy and you desire a free solution. If you’re willing to spend some money on a capable audio editor you might look at HairerSoft’s $25 Amadeus Lite or Felt Tip’s $30 Sound Studio (Mac App Store links).
Within your audio editor make sure that the Mac’s line-in port is selected as the input source. Load the first cassette of the set into the tape deck and start it playing. In the audio editor check the input levels to be sure you’re getting sound into the application and that the sound isn’t too loud or soft. When you’re satisfied with the sound levels, rewind the tape, press the audio application’s Record button, and start the tape playing again to record it. When side one is finished, stop the recording and save it with a name that helps you keep the various recordings in the proper sequence—MyBookTape1Pt1, for example. Flip the tape over and do it all over again. Repeat for each tape in the set.
When you finally finish you can treat these recordings just as you would audio files you’ve ripped from a CD. You can import them into iTunes, build a playlist around them, and then sync them to your device. Or, as I described when talking about ripping audiobook CDs, you can use Join Together or Audiobook Builder to combine the files into a single track.