My wife and I have been traveling like this since 2009. I was self-employed for many years before retiring, so vacation for me has always been at my discretion. She, however, worked for an employer who insisted she could not take more than two weeks off at a time, even though she's been there long enough to accumulated like 7 weeks annual leave each year.
So in 2009, we took US 2 clear across the Great Plains to Seattle to visit a friend. That burned up her two weeks, so she flew home, and I dragged the TT south to LA to visit our daughter and SIL, then back home.
Later I had a professional conference in Vegas, so dragged the TT out, stayed at The Oasis Resort, and when my conference ended, she flew out, and we spent her two weeks making a big circle around the Grand Canyon and taking in Bryce and Zion NPs while we were at it. She then flew home and I dragged the rig back by myself.
Most recently, I spent a week by myself taking the TT to Albuquerque for the Balloon Fiesta. She flew out to meet me, and we took in Taos, and the many towns on the road all the way back home together.
We've been married now for 50 years, working on 51 (I was a child bride) and she's retiring later this year. We're looking forward to more trips together, but she'll likely go with as well as return with.