It sounds like the original poster does not want to be a road warrier, always on the road, tired of travelling.

The route of presenting a paper (university faculty) works except they will see the same cities over and over again as meetings are often in the same cities that have lots of hotel space.

To me, the person is looking for a job with enough vacation time. If they earn enough (or even not a whole lot), they can fly off season often. US-Europe flights are very cheap in the winter. It's not that cold. If they have time, they can also fly to the Far East or Australia.

I wish I had enough time to visit Tristan. They have no airport. There is only an infrequent boat from St. Helena. I figure that you need a minimum of 6-8 weeks of vacation time to visit the island.