Well, you have plans for a long day hike over some fairly strenuous terrain but your boots are not in any condition to take a hike on. So don’t buy new boots a day or two before the trip- this will guarantee a good deal of pain, blood and discomfort. So the trick is to break the boots in over time before going on that hike. Wear then in over diverse terrain which even includes walking in the city and local parks. Stiffer leather boots will require more breaking in than the more modern synthetic variety that is easily broken in over a shorter period as they even have fewer restrictions in the heel area, yet they will not last as long over trails when compared to a leather boot. You could break the boots in around your house and garden but adding weight and elevation makes a big difference, it’s a different dynamic, hence the suggestion to use a walking train in an urban environment and carry a weighted daypack. Delta Park in Johannesburg is a good example of such a trail. A reasonable break-in period is around four weeks which sees you mainly wearing the boots every weekend for at least a few hours on Saturday and Sunday. Try and hike in different conditions and even try rock-hopping across a small river or stream as you may encounter this type of obstacle on the actual hike, don’t be afraid if you get your boots wet they can easily be cleaned and dried.
If you know the actual distance of the trail you are going to hike try work to a point where you are comfortably able to walk that distance in your new boots. However, if you opt for extremely lightweight hiking/trail shoes then you do not need to be extreme in walking the full distance.
With leather boots its often worthwhile wearing a lighter sock over a thicker sock and for the first few hikes wetting the thinner sock, I find it helps the leather stretch and conform.
Once you have had your first walk examine your feet for red spots where chafing may take place, remember while you are breaking in your boots you are also doing the same for your feet and don’t want to develop calluses or blisters.
Once you feel the boots are getting more comfortable experiment with various socks until you find those that you are most comfortable with. Then experiment with laces, there is nothing worse than lacing up too tightly, the resultant pain can really spoil hike, laces that are too loose however will cause chafing as you foot moves within the boot.
Vaseline is useful for chafing as is foot powder, one can also get pink “moleskin” pads to alleviate pressure on an area. And lastly avoid the temptation to pop a blister, the excess skin will tear away leaving a raw would.