Where's a good place to start?

We are taking my kids for the first time next week. To practice both the packing and travel style, we bought them convertible backpack suitcases, and took them for 10 days to Philly/Annapolis/DC/Williamsburg. We stayed in about 5 hotels, and traveled by train, subway and car. It was a great opportunity for them to learn the STYLE of travel before we left the continent. And, it was LOTS of fun!

Dan,

If you want to ease into the European experience in a nice, laid-back way, you can't go wrong with Amsterdam. Friendly, open society, lots of history, easy traveling experience. I don't think you'd have to do a dry-run first in the US for that. You could consider Amsterdam your dry-run for the rest of Europe.

Wow, that was quick. Thanks for the advice so far.

Is the language really not an issue in Amsterdam? (I only speak English) At least for a first trip, that is one headache I wouldn't want to deal with.

That's why I recommend Amsterdam to start. Language is really NOT a barrier. So many of the dutch speak English that even if you did know some dutch, you probably wouldn't get a chance to use it. Inside Amsterdam, you virtually won't run into anyone that can't speak English. In the countryside, you might, but it would be rare.

I agree with Amsterdam for the language part and it is a facinating and young city. The price is better than London, Dublin or Edinburgh, so that is in your favor, but you can be as adventurous of safe as you want to be. YHA (Hostels) make staying cheap and if you learn the trick of eating a picnic for every meal, you can go cheap. You might want to check out Rick Steves' son's blog about his summer in Europe "on the cheap" http://www.ricksteves.com/plan/destinations/europe/aablog.htm

On the "dry run" I say just go for it. If you want to visit Boston or New York anyway, fine, try the dry run, but reading suggestions here and packing light, you'll do great and part of the adventure is just doing it.

I grew up near Boston and went to London for a week in high school, and maybe I was way off base, but London reminded me of boston - a lot. I still remember thinking to myself "This feels a lot like Boston". I think Boston is probably the most "european" big city we have in the US (it's still quite a stretch, but there are similarities). So, maybe i'm a little bit biased, but if you haven't been to boston, you should go anyway. =) I loved London and I am going to Amsterdam this summer, I think you should go somewhere that you think will really jive with your own interests - all of the cities in Europe are wonderful. London is OUTRAGEOUS - on top of the sheer horrendous exchange rate, things are more expensive there anyway. Maybe get a couple of Rick's books from the local library and read about stuff to see what you might be interested in and go from there?
at any rate, whatever you do you can't go wrong, and you will have an awesome time. go for it!

I think your best choice for a practice run would just north of the border in Montreal. But my advice would be to just go for it. One of the joys of travel is getting immersed in the cultural differences. I personally get a "rush" whenever I arrive in a new country with a different language, alphabet, money, transit system, etc. Just study up on the various guidebooks/maps and you will be fine.

It was Europeans who transfered to America, settled, built a country - the US. And they built it after what they knew from back home, from Europe. So actually Europe isn't that different from the US. Thailand, e.g. a country that's never been colonialized by any European country is a complete different story. But back to the case. In most European countries English is a language spoken at least in the services industry so don't worry about that. Amsterdam is a bit of a more chaotic place so is Rome. You could do any of the European cities for a start: London, Paris, Berlin, Rome, Munich, Vienna, ... What kind of night life are you into, what kind of clubs, music, scenery?