this is totally possible depending on what sort of writing you want to do. My dad in his retirement from being a PR consultant has turned himself into a freelance travel writer and is now able to get invited on these press junkets to various places and then writes about it and publishes in local newspapers and some national magazines. He gets a lot of free trips he has a lot of fun on. He just got home from a trip to Florida where he got to ride in a 1930’s biplane and go kayacking. This sort of thing might ruin your desire to travel for pleasure not work, but if you would find journalistic sorts of writing fun it is a way to finance the trips. Then if you were wanting to to do more reflective writing you could do that too.