I prefer Kayak Explore for flexible itineraries since it basically just shows you the best price everywhere and you can filter by price, time of year, flight length: https://www.kayak.com/explore/
EDIT: And here's a ridiculous itinerary it found for reference:
SO good; thank you. Will start visiting random places.. thinking the formula is AirBNB + friends + random interests (tennis/spin) and long walks at the very least.
Hitlist (hitlistapp.com) is also designed specifically with flexibility in mind - we don't have every single route on every day, but we let you set an alert with whatever criteria you have in mind - from 'SFO to London on these days +/- 3 days' to 'a beach in southern Europe for 7-10 days between January 8th and 31st' - and can ping you when fares that match come up.