I am >50 with grown up kids: this is how we spend our holidays and we get not much more then the "American 2 weeks". Planned is just the timeframe & means of transportation, the rest is pure accidental. We run in to the most boring places and move on, we hit the most surprising gatherings, fall in love and stay. Whatever happens we decide on an hourly basis what to (not) do next, exactly that what we cannot do in our daily lives. We find that it takes on average 3 days to completely reset from city slickers to travelers: hygiene rules change, food preferences, clothing & make up, luxury requirements, sleep rhythms & most of all the perception of time.

What age were your kids when you started with this style of traveling?

When I was in grad school, this is how I traveled each summer with my brother and cousin. We'd pick a country and have our first night (maybe a couple of nights) accommodations picked out and then let the feel of the day guide us. Some of our best times were with random people we'd meet at the hostel and then travel around with for a couple of days before going our own way.