I’ve done the trail you’re doing. We stayed at one end and paid someone to drive us to the other so we could ride back to where we started. The place we stayed was TERRIBLE, but the ride was fun.
If you live fairly close by, I highly recommend doing the GAP trail at some point. We did it with Wilderness Voyagers, which is towards the lower end of “luxury” or whatever in my opinion, but they were fine for that trip. I know several people who’ve done it on their own.
We’ve done multiple “active adventure” trips, mostly cycling.
In Europe we’ve only used a company called VBT, and we’ve done the Dolomites (the valleys, NOT over the mountains), Tuscany, and France/Switzerland. The one I’ve heard the most people rave about is Croatia, but I haven’t done it myself. NOTE - if you’re interested in VBT for next year, they usually run something between about now and mid-October where if you pay in full, you get 5% off. They also let you buy your airfare, along with pre and post trips (a couple of days in a city before and after) as a package, which is what we’ve done.
We used Active Adventures in New Zealand. It was a 14 day trip.
We did a hike, bike and helicopter trip to the Canadian Rockies with Backroads quite some time ago.
Some people have said Backroads is more luxurious, and some people say VBT and Backroads are very similar.
We’ve used Sojourn for multiple US based trips, but at this point I wouldn’t recommend them.
If you’re a cyclist, and NOT wanting to use e-bikes, pay attention to how many people on the trip are using e-bikes. Our Tuscany trip was the first one where there were many more using e-bikes than regular.
I think size of group matters, and it’s worth asking the average age of people on the trip, how many are groups, couples, singles. In our experience most groups are welcoming to other people, but not all.
Make sure you understand when a trip is actually “locked in” so you don’t wind up with the rest of the trip planned around the cycling, and then find out the trip won’t happen.