I've been meaning to ask, how do you go about planning your trips? I really want to travel a bit this summer, but I never have (out of the states) and I'm a little intimidated.

Well for a start, the majority of actual planning is generally (read: every trip so far) done by the girl. She’s pretty wonderful, and often unwinds by planning future trips (often even ones that we actually end up taking)!

But as a general process (that can be swapped around depending on specific circumstances):

1. Work out when you want to travel (cost is greatly reduced the further in advance you are able to plan).
2. Decide on a shortlist of destinations. Don’t cut anything back at this stage - just brainstorm all the places you think you’d like to go at the time you’ll be travelling.
3. Look up flights for each destination, at the time you will be travelling. Sites like Expedia.com (best for flights within Europe) and Webjet.com.au (for trips to/from Australia) are your friend! Use them to get the best prices and transfers, and then (and this is important), book the flights through the airlines themselves (to save on booking fees)!
4. Decide on your destination/s! (We usually like to visit as many places as we can in a trip, but spend at least a week at each place. This rule has been broken though, and we’ve never yet regretted a trip we’ve made.)
5. Book your flights. The sooner you lock them in, the cheaper they’ll be! Also, every other decision will magically become easier and more fun once you’ve committed to your holiday! (Remember to check those fiddly things like baggage limits and meals provided on long-haul flights!)
6. Book your accommodation. Look up all the options first, from backpackers’ hostels to five star hotels - you never know what you’ll be able to afford! One site we’ve used a LOT, to incredible success and happiness is AirBnB.com. It allows you to book people’s properties as you would a hotel - people rent out beds, rooms, or entire houses or apartments - and book them through PayPay, making the whole process much more reliable than similar free sites like CouchSurfing.com. It’s awesome - we generally aim for the “book out an apartment” option (which tends to cost a bit less than a low-star hotel room, while allowing us the use of facilities unavailable in hotels), but we’ve also had success with “book a room”.
7. Look up shit to do there. This can become a great pastime for the coming months, as you motivate yourself to get through the year with the promise of an awesome holiday that you’ve already mostly paid for! Don’t feel pressured to book it all as early as the flights and accommodation, though. You won’t save much (if anything), and you’ll appreciate the freedom later. But you’ll also appreciate having looked it up, and possessing the information!
8. If necessary, book a rental car. I said if necessary, because you probably want to avoid driving in a foreign country unless completely unavoidable. It might be necessary though, and in that case you’ll definitely appreciate having booked it!
9. GET TRAVEL INSURANCE. You can even book this earlier. Maybe right after booking your flights. Don’t debate the odds of claiming versus the cost. You can compare companies, but MAKE SURE YOU GET THE INSURANCE FROM ONE. In fact, I’ll make this #10 as well.
10. GET TRAVEL INSURANCE.
11. Go on your trip! Leave your marking, your work laptop, your personal drama, and pick up and go!
12. Be prepared to change your plans. You know all those things you looked up in the past month? The alternate flights, backup activities, and travel insurance you bought (right)? That’s because shit happens, and stuff goes wrong. You’re on holiday, and all that stuff was to make sure you have a damn good holiday whatever happens. Hell, even if a monsoon hits and you spend a week stuck in a motel room in Thailand with no power and grounded flights - you’ll no doubt have brought plenty of books that you meant to read all year, and there’s bound to be a café or pub nearby. You’ll be fine.
13. Leave no regrets. Remember, this is what you were saving for. You won’t regret that extra wine, those shoes, that tshirt, that handbag. Work out the minimum from your savings that you’ll need to leave untouched, and go nuts on the rest!
14. Come home, and try not to drive all of your friends and family nuts as you talk constantly about your amazing life-changing experience. Or do. Screw ‘em, it was your holiday.