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The original was posted on /r/bicycletouring by /u/No_Ant_5064 on 2025-10-19 22:31:08+00:00.

Basically, as a full time office worker with limited PTO, I’m used to planning trips down to the day, figuring out pretty much what I’m going to be doing every day and where I’m spending each night long before the trip even starts. So far I’ve been doing the same with my bike tours.

However, I imagine the longer the tour gets, the less able you are to do that. So I’m curious what you guys do. Do you preplan everything? Figure out where you’re going to sleep each day of? Or somewhere in between were you know you have to be in this town Monday of next week but wing everything up to that? do you prebook the return train or flight and just hang out for a few days if you make good time?