You might have time to train and build up for 100 miles a day. Five months is a long time and you and your friends are young.

But you also need to go longer some days (maybe 130) to make up for bad weather, mechanical issues and mountains.

While you physically might be able to train and accomplish a trip like that, it won't be fun and you might end up with chronic fatigue. Better to set your sights on something less ambitious.