I think you need to think carefully the plan of taking your teenager DS away from school for a few years to travel. As an expat, we moved around a lot, and as my DCs getting older it became increasing difficult, mainly for continuity of schooling, and their friendship group.
I totally understand the excitements and adventures of seeing the world, and to a certain extend it is a valuable education to them of knowing and experiencing different cultures.
I think if you are planning to stay in each city or places for few months, and then move on, it will be very difficult for your teenager DS to make any friends. And people in general will not invest in friendship knowing you aren't staying long.