Originally Posted by
Shiloh253
-Making sure I'M capable as well. Sometime next week I plan on doing a 25 mile trip to the nearest town and then taking a bus back, just to see how I handle that.
-Spending at least a few days a month practicing living out of my bike.
It depends on how you want to do it.
100 miles in a day isn't bad, although it becomes a bit of a drag doing several 100 mile days consecutively.
Why not do your 25 mile trip as a 50 mile Round-Trip? Start early in the morning, and just ride... and ride... and ride.
Jumping from 20 to 40 to 60 miles.... is all that big of a jump.
Some training always helps.
I'd start collecting the gear you'll need for the big trip if you don't already have it. Tent, Sleeping Bag, Rack, Panniers, etc.
I'm not sure I'd like to drag a trailer 350 miles, but it could be done. Just get a used Kid's trailer and fill it up.