Well, Iwe have a variety of speakers sets now, so a quick long term review and then on to finding a good portable system:
* JBL Creature II. These are PC speakers so for listening in a whole room and is the 21st century version of bookshelf speaker set. They sound OK. 4/4 on playlist, the main thing is that they are cheap at $80 and good looking. The sound quality is OK and works well for near field. I don't turn it up too much because it is at work, but a good, but not great choice. 4/5
* JBL Onstage. These are the nicest looking speaker sets and looks nicer that the iM3. It's main use is for casual listening. Think clock radio. I don't use it anymore, because, I torqued the dock connector by pushng in. The new Creature II now includees a wireless remote but is otherwise the same. It doesn't have batteries, but is way prettier. 4.5/5
* Altec-Lansing iM3. This was the first portable system. It includes 4 AA batteries and a charging brick. Its sound quality is OK and it makes the iPod a portable clock radio really. It sounds tinny to me and there is no bass. The best use I've found for it is as a clock radio for waking up in the morning. For me as ultralight traveler, it is really too big to carry on the road. 4/5
Now hoever, real boomboxes that have great sounjd are coming out that have a Ipod dock and look nice. Playlist: Product Guide: Speakers for your iPod has a good overview. The basic idea is a high quality speaker set, portable and ideally with batteries. The Apple Hifi is $350 and probably the best compromise although it doesn't sound as good. Here4 are some other choices if you don't want to give everything to Apple:
h4. Boombox transportables.
These are models to consider if you want something semi-portable. That is, they are small enough to move around. Kind of in the boombox category, but sounding better. Some have batteries, but some don't. In order of what looks good right now I'd get:
* "Monitor i-Fi".http://playlistmag.com/reviews/2006/04/monitorideck/index.php. 4.5/5. $250. These guys make really great speakers for audiophiles and the sound quality is very good. This isn't actually technically a boombox. The spekaers separate and it doesn't have a battery mode., The sound quality is very good though, although not as loud and "boomy" (e.g., it is more accurate than others). It has less bass, but is more accurate.
* "Audioengine 5":http://playlistmag.com/reviews/2006/03/audioengine5/index.php. $350. 4.5/5. These are bookshelf speakers with a builtin amplifier. Sound quality is very good as you would expect with real bookshelf speakers. Not surprisingly, its bass is better, but the Monitor's are more accurate in the treble.
h4. Boombox with batteries
* "Altec Lansing iM7":http://playlistmag.com/products/complete/180-detail.php. IMHO this is the coolest looking speaker set, it looks like a big tube with an iPod embedded in it. $150. 4.5/5 by Playlist. It's portable and sounds as good as the Bose SoundDock so not a bad choice. It is really a boombox and competes with the Apple iPod Hi-fi directly.
* "Apple iPod Hi-Fi":http://playlistmag.com/reviews/2006/03/ipodhifireview/index.php. 4/5. $250. This is Apple's own boom box system. It is nice looking, but it is "boomy" so it sounds a little muffled. Also, the iPod kind of sits at the top, so it doesn't fit very well into an enclosed area like the Altec Lansings do.
h4. bookshelf on home speakers
While we are at it, there are more and more speaker systems that are powered that work well for computers or iPods including:
* "Altec Lansing FX-6021":http://playlistmag.com/products/complete/53-detail.php. Like the JBL Creatures, these are really designed for PC listening, so called near field listening. $150., The nice thing is that it has two audio inputs, so you can hook it up to your computer and also your iPod without having to reconnect the 3.5mm plug.
* "Audioengine 5":http://playlistmag.com/reviews/2006/03/audioengine5/index.php. 4.5/5. $350. These are bookshelf speakers that include an amplifier inside them. The sound quality is on par with the Apple iPod Hi-fi. You can also plug in an Apple Airport Express so that you can stream music from your PC to these speakers. Kind of cool if you like streaming. Most folks find the Hi-Fi mid heavy, but these apparently sound more balanced and accurate.
h4. Clock radio iPod
The key features here are that it has to be small..
* "Tivoli Audio iSongbook":http://playlistmag.com/reviews/2005/11/isongbookreviewfinal/index.php. $330. 4.5/5. I actually have a Tivoli Clock Radio for Connie and its sound quality isn't bad. This is the dedicated iPod version.with a flip down connector set. It also has an AM/FM radio and a pair of 2.5" speakers so it doesn't have the bass, but the speakers are actually very good for "clock radio" listening.
h4. Portable iPod
This has to be small and portable but decent sounding. You could also use this as a standard clock radio but then you don't need the batteries and get a better sounding system (see the above).
* "Logitech mm50":http://playlistmag.com/reviews/2005/08/logitechmm50/index.php. 4.5/5. $150. It is larger than the iM3, but has a rechargeable lithium ion battery and sounds much better. So its not a boom box, but for putting on your desk as a clock radio, it competes with the JBL OnStage but with better sound and it is a good portable system.