It is far and away a problem of too many options. There are dozens of flight aggregators, airlines, and potential destinations, and somehow from all that picking one flight to one location seems daunting and overwhelming.
Our situation is a bit different than the average traveler I think, because we're very flexible about where we want to go. I'm more than willing to let ticket and hostel prices dictate where we go, because I know that this is only the beginning of our travels, and I'm not hung up on getting to see one specific city or country at this point.
What I really need is an aggregator that will tell me the cheapest airline prices for various cities without having to search each city individually. Does anyone know if that exists?
Right now we're leaning towards either Rome/Florence or Milan/Florence, depending on which city is cheaper to fly into. I think Italy would be a beautiful place to visit, but it certainly looks like it's going to be more pricey than Athens. I suppose that's one benefit of visiting economy ravaged countries such as Greece, the prices seemed cheaper than elsewhere in Europe.
Despite the self inflicted stress of travel planning, please don't think for a minute that we regret or dislike traveling. I'm so grateful that we have the opportunity to do so much of it now, as opposed to the mind set of waiting until we're more established.
Hija de la Luna had a great article about this, and I completely agree that finding ways to travel in our twenties is a high priority before we allow ourselves to get tied down with jobs, family, and the ordinary challenges of life that prevent international travel.