Couchsurfing.org -With this site, you can find someone to host you for free, offer up your place for fellow travelers, or just link up with folks while traveling. It may sound a little sketchy, but you can read reviews before you make any decisions. And make sure to leave honest reviews for other travelers’ reference!
Skyscanner.com, Kayak.com & Expedia.com -Usually using these sites are the best way to find the cheapest flights. Though, sometimes if you’re flying locally, it’s better to visit an airline’s own site. (In Asia, AirAsia.com and NokAir.com are also good sites to know.) With Kayak and Expedia you can also search and book hotels, rent cars, and do some other fancy stuff I haven’t tried.
Travel.state.gov -I find myself on this website a lot when I’m thinking of going to a new place. You can find out if you’ll need a visa to travel to a certain place and how to get it, if there are any vaccinations you should consider before going, if there are any travel advisories for the country you want to travel to, and more.
World Nomads -Insurance is always an odd deal. If you don’t need it, it feels like a big waste of money, and if you do need it, well, good luck. I was fortunate enough not to have used my travel insurance from this company, so I can’t offer any reviews on how the cash in worked out, but I can say it’s very easy to sign up and extend as many times as you need throughout your trip.
WWOOF -This is a cool site where you can pay $15 a year to link up with organic farmers around the world, and potentially learn the organic farming biz with them, usually working for food and accommodation (you will work out your arrangements with your host). I haven’t tried this one yet, but a friend did it in Japan a few years back and had a wonderful experience.
Australian Gov’t. & Jobaroo -Here are a couple links with information on another adventure I haven’t tried out yet, but know many people who have: obtaining a visa to work for a year in Australia. The first link is the country’s government site with information on eligibility for the aforementioned 462 visa. You can find the same info on Jobaroo, but this site also has some job listings, info on travel insurance, opening bank accounts, and more.