There is a nice concept I've read I think on either Orions Arm or Project RHO about basically settling the Kuiper Belt and the Oort Cloud.

It would not really be about primarily traveling anywhere, just people settling this are with its immense resources over many generations, until possibly the ones on the furthest reaches would be able to make the jump to the next systems Oort cloud & slowly settling it down the gravity well, maybe even reaching the inner system eventually, provided something so tiny and sweltering would be of interest for them by that point. ;-)

IMHO this is actually much closer to how humans spread along the Earths surface. It was no like someone just get up and walked from Afrika to Australia. The various human group just expanded their habitat over time until they spread all over the place over many thousands of years and this would be similar.