Have you done anyt touring? If not, you might want to start with something smallish to begin with. You can pack a lot into two weeks. The GF and I have done 2 trips starting in MT in the last four years. 9 days of riding. Travel Thursday, start riding Friday, finish riding a week from Saturday. Because of the four weekend days, we only used 7 vacation days. Not even 1 1/2 weeks off from work.

As for much longer trips, we all make choices in our lives. At age 34, with (voluntarily) no mortgage, no wife, no kids and no pets, I was free to take two years off from the working world when I was downsized in the wake of a corporate acquisition. In fact, I volunteered to be laid off. Did three long tours, pursued other interests and saw a lot of matinee movies.