San Antonio - to Alaska - why !?? Gets real cold up there - don't ya know (and DARK) (and the mosquito is the state bird!). Otherwise it is beautiful.
Vansolo is probably correct. Probably take a 2000 lb tandem trailer. About 6000 gross for the Tundra to pull. Thats a load.
You may want to price shipping the Highlander. You may be able to drive it in a day less and save a lot of gas (and wear and tear). My .02.

SD