If there is one thing I do not like to do when going on a long-term trip, it is making reservations more than a week in advance. The freedom of being able to travel for months on end is something that allows us to be completely flexible with our itinerary, extending or decreasing stays in an given city at our discretion.
When going on our next 14-18 month trip, we were overjoyed with the fact that we would not have to plan very much in advance and could roam on our idealized itinerary. Then we added Europe into the mix. In the summer. After counting the number of days we were hoping to spend on the continent, we realized that we were getting dangerously close to the 90 day visa limit for the Schengen Area while also having to combat the hoards of travelers during peak season. Just like that our hopes for a reservation free long-term trip came crashing down. To lock in the good deals in peak season, and to force us to fit within the 90 day Schengen visa limit, our bookings began and thousands of dollars were spent.
The logic of booking in advance during peak season is obvious. But the need to craft our itinerary to fit within the limits of a free Schengen visa may not be as apparent.