[ma-skis.com]

SE asia for monetary reasons, australia if you're nervous about travelling on your own.

both are pretty safe regardless, or just thailand after australia, it's cheap enough that a couple grand will buy you a few weeks.

EDIT:

Re-read the post, and I'd say start with australia then Thailand since Australia would be in there winter by june/july. Short of staying north of brisbane, you'll get 10-20 degree days. Which sounds good, but to me australia is all about +30 days on the beach. Working is easy enough down there, you can get the 3 month work visa and just do about any entry level work. I worked in a restaurant and bar on the Gold Coast, a buddy picked fruit somewhere in the outback. I wouldn't expect a job to pay for stuff other than to maintain status quo for as long as possible, if you think it'll be like save up to go to thailand, that is very doubtful.

Really you should check out the work visa for a number of places while you're under 30. Apparently there's a bunch of countries that offer that to make travelling more accesible to the younger crowds.

Thailand and Australia are both pretty English friendly and travel friendly, you'll meet lots of other travellers and pretty much party all the time.

And i'd stay away from europe for now, it's expensive and not as tropical.