I, too, am retired and my wife works and doesn't bike.
What I try to do is to try an incorporate a trip to an interesting place on both ends that we can both do. For example, on my recent Atlantic Coast trip, we visited family in New Jersey, she returned home and I rode off. At the other end, about a month later, I met her in Boston (she flew, I rode) and we spent a week in Burlington Vermont. I did the same thing on an Oregon - Yellowstone tour. On my trip across France, she met me in Avignon at the end of that ride, as well.
I always make the suggestion of a nice place to visit near/at my starting/ending points. Often, she like the idea and we combine the vacation/bike trip together. Sometimes, she can't get the time off or isn't interested, so I got off by myself knowing that I tried to make it work out.
Ray