Husband and Wife Seeking Winter OTR Work

My wife and I are looking for winter work outside of Alaska from November through mid-February.

I've been driving mostly log trucks. Also dump trucks, and tankers for 25 years. I am also a mechanic. Never had an accident or ticket in a truck. I have never done OTR, but sure would like to.

My wife is a mariner and drives fishing boats and tour boats from April through October. She does most of her maintenance, too. She's planning on getting her Class A this year and we would love to find a way to work together in the time we have off. We can travel to anywhere in the country. Love being on the road. We are both meticulous about maintenance. We are very hard workers and motivated to save up some extra money in the winter (I fly planes, too).

We want to find consistent work that we can come back to each year in the winter. We've been picking up work (My family runs a logging operation in Oregon, my wife does off-shore ships), but are tired of spending our winters apart. Is this possible or are we dreaming?

If it matters, I'm 44 my wife is 35, been married 11 years in June.