Hi, Not sure this is something that can be hacked (yet) but travel has a few distinct steps: Discovery, Planning Booking. From your post it sounds like you are

Hi, Not sure this is something that can be hacked (yet) but travel has a few distinct steps: Discovery, Planning Booking. From your post it sounds like you are still in the discovery stage so you can use sites like TripAdvisor, Gogobot or Desti (there are a lot of others) to discover. Unfortunately I have found that a lot of these are complicators and not simplifiers. Once you know where you want to go and what you want to do you can use OTAs or companies like Hipmunk (flights) and AirBNB for accomodation booking. There are a few companies that offer complete trip booking including activities etc. but these are typically limited to specific locations. I know of a few around Europe. The other question is what type of trip this is? Sounds like you are looking for a vacation with multiple stops which makes the process more complicated but also fun. If you know your destination and type of trip I might be able to give better pointers. We are working on a much better solution at OlSet that will simplify the process but we will not be ready for prime-time until Q1 2013.