www.headphone.com will solve all your issues. there is no compact and portable system works better than a nice headphone setup.
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I use a Grado headphone amplifier which is relatively compact, gives reasonable battery life with a 9 volt battery and sounds very good with headphones.
Do you wish to carry CDs and a player of some sort or are you willing to use a computer and compressed formats for your listening material?
If you intend to be computer based, I would love to hear from anyone who knows if there are notebook computers available with audiophiley, line level outputs or DACs?
One other tip: I have never tried them, but a company called Monsoon made two little planar speakers for use with computers. Two speakers with a little sub were small, very cheap (<$150) and Stereophile claimed they sounded surprisingly good when listened to in nearfield.
Nothing makes me Happier than my iPod (www.iPod.com) running through my Headroom Supreme (http://www.headphone.com/layout.php?topicID=3&subTopicID=27&productID=0010012000) then feeding my Sennheiser HD580's (http://www.headphone.com/layout.php?topicID=3&subTopicID=26&productID=0020080580).
But If I'm on the plane, the iPod has enough juice to feed my Etymotic's (http://www.headphone.com/layout.php?topicID=3&subTopicID=26&productID=0020100000).
I've been very happy with the sound quality of my Sony Minidisc player when driving Grado SR-80s. I record straigth from the audio output of my Classe DAC, but Sony also sells an cable that allows you to input a digital (Toslink) signal, so you can go direct off your CDP if you have toslink out. Haven't experimented yet with my Senn HD 600 to see if the MD will drive it.
Marakantz is right. Headphones, particularly the Etyomatics are great on the plane. Couple it with the airhead amp and (don't shoot me here) the MP3 jukebox (it's actually quite good if you don't over compress and holds hundreds of CDs) and you've got a really great compact system. If you don't want to wear headphones in the hotel, MP3 has some really small portable speakers using "flat" technology. How do they sound--like you would expect for $80, but tolerable for low volume background music while working on the computer in hotel rooms--I know the routine all too well.
I travel weekly as well, ain't business travel glamorous? When I travel by car I bring along my Swans M200 powered speakers and my Panasonic portable CDP. The Swans weigh 40 lbs and are bulky, not ideal for plane travel. But..damned nice speakers for the size and cost, highly recommended! Plane travel..jeez I had plane travel. Anyway, I've logged hundred of thousands of miles on planes and tried a few different set ups. First up was an older Panasonic CDP with a pair of Grado SR-60 headphones. Not bad sound, and the Grado earphones swivel so they lie flat. Handy, but the sound wasn't terrific and they're uncomfortable to wear for more than an hour. Next up...a Headroom Airhead amp, a new Panasonic CDP, and Ety headphones. I returned the Ety's after a week, so uncomfortable I couldn't use them. Maybe I have odd shaped ears, I dunno. My current set up is the Panasonic CDP, Airhead amp, and Sennheiser HD600's. Stuff the gear and a dozen CD's in a knapsack as a carry on and I'm good to go. Yeah, the Senns are bulky but worth the extra space, they sound terrific and I can wear'em for hours and hours.
For the past 5 years, I have travelled (both domestic and international) with a Cambridge Soundworks Table Radio (Model 88) and a portable SONY CD player. Both fit nicely in a small gym bag and weigh a few pounds. If you are staying in the same hotel for a number of weeks and are just returning home for the weekend, you can check the bag with the hotel concierge, lock it up in an office desk drawer, etc. Relatively inexpensive ... $150 for the radio; $75 for the CDP. I would imagine that you could do this with the Tivoli radio, as well.
I just tried my HD 600s with the MD player, works fine. Won't match the Airhead/CDP HD 600 combo, but each MD is about 1/4 the size of a CD and if you're traveling by air you can use the compression (not sure if its actually data compression or what) to store 5 hours of music on a single MD. So in the space of 1 CD, you could carry 20 hours of music, and the player is less than 1/4 the size of most CDPs (about 1/2 size of a pack of cigarettes). Another advantage is that it runs on a single AA and they last quite a while; a four pack would seem to me to easily yield a week of listening several hours a day.
I agree with the recommendation for the Cambridge Soundworks Model 88 radio paired with a portable CD player. I put together the same combination and was amazed at how nice it sounded for the money. The radio has an excellent tuner section, decent speakers with variable bass output and wonderful remote control the size of a credit card.
I bought a refurbished Model 88 for $106 on ebay from hifi.com, the online outlet for Cambridge Soundworks and a very nice Aiwa portable CD player for $39 from returnbuy.com. Added a stereo mini-plug to RCA adapter and for $150 total I was set. Even if you think this rig is too large for travel, it makes a great office or bedroom system.
As an aside, the service from Cambridge Soundworks is exceptional. When the Model 88 arrived it was DOA. I called the service department at Cambridge and they apologized profusely, immediate FedExed a replacement (which was a new unit, not refurbished) along with a prepaid shipping label and asked me to return the defective unit in the same box whenever the new unit arrived. An entirely pleasant experience.
I definitely concur with "Marakanetz" when he says that you should go to "www.headphone.com". Anything you need to know about high quality portable audio, they got you covered there.
I have a "portable/traveler" stereo myself (which I use mostly for the office, but sometimes, I go out of town too, and that means that sometimes, I need to listen to my tunes in a motel room too....... especially when I am in for the night), and I haven't had nothing but great times with it each and every time I use it. It doesn't quite match the home rig as far as ultimate sound quality is concerned. But for what it is, it is an excellent system considering the purpose for which it is used for. So, that alone is saying a lot.
Again....... I'm happy with mine. And when you finally assemble yours, you'll probably be happy with yours too.
P.S.: PORTABLE SYSTEM:
Sennheiser HD-580 Headphones
HeadRoom Total AirHead Headphone Amplifier (the 9 Volt version)
Sony D-EJ815 CD Walkman
Straight Wire Short Portable Interconnect Cable
HeadRoom Leather Portable System Bag