Originally Posted by
TheFlyingDoctor
I'm naturally quite cautious myself - the groundwork described definitely helped convince me the plan was viable, as did firing up room booking apps now and again to see what could be had for a sensible sum that night in a variety of cities. The backup plan was to have a 'support team' by letting my partner know where we headed and have her figure out accommodation whilst we were in the air. Another option is to make fully refundable bookings (on points, perhaps) in each city from your shortlist so you know you have that covered once you make it onto a plane - although there is then the hassle of cancelling all the others!
I think I can get her to go along ("it's an adventure.") with a roughly-defined destination list. We both know that barring special events, if you're not too picky a traveler (we're not), you can always find a room. As you say, so easy with online booking engines.
A few years ago (before I met my SO), on a whim, I grabbed a taxi from Athens to Pireaus and took the next ferry out. Then spent 10 weeks just going from island to island on wherever the ferry was going when I got to each port ( barring return to the mainland). No internet, not even a mobile. Maybe my favorite trip ever.