1. Create a Smart Playlist. Choose "New Smart Playlist" from the File menu of iTunes.
2. In the dialog box that pops up, there are two primary drop-down menus. Click on the first one (on the left), and choose "Media Kind" from the list. Now there will be three main drop-down menus. In the third one (on the right), choose "Podcast" from the list. You should now have the following rule: "Media Kind is Podcast."
3. In the center of the dialog box you'll see the phrase "selected by" followed by a drop-down menu. If you choose "highest rating" from the menu, your podcasts will appear on the device in order of which have been most highly rated by other users, which is nice.
4. Click OK.
Now, when you synchronize your iPhone or iPod, the podcasts you sync will be available in the Playlists area (button on the left in the iPod app). If you press Shuffle, they'll play in random order. If you click on a podcast to play, it will automatically place the next one in on the list, then the next, etc.
This tip was adapted from How to set up continuous podcast play on the new iTunes by Mike Elgan.
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