Hey all, home sick today, so I'm catching up. I think I'd attack this a different way. Carol has a point.
1. I'd start at Many Glacier. You can hike about any direction, but Iceberg Lake, then Grinnell Glacier, and then Cracker Lake. Each of these is a pretty significant hike (10-12 miles RT and a couple feet of vertical), so I think the average person probably won't stack these back-to-back. Pick two or three of these and you'll be good for 5 days.
2. Logan Pass area. Highline (with option to Many Glacier--15 miles), Hidden Lake (even going down to Hidden Lake), and the Siyeh Pass loop (ok, it's close to Logan). Both the Highline and Siyeh are significant hikes again, and most people probably won't do more than 3 significant hikes in a week vacation unless they're athletes.
3. Two Medicine is beautiful, but the main hikes (Pit-Daw, Scenic, Cobalt) in that area are really stout unless you do a shorter out and back hike. I'd probably skip that on the first trip unless the hikers are in shape. Then Dawson-Pitamakin is excellent, but also 19 miles. I first heard about this hike from a guy that ran the route.
4. Then there's the "I'm tired and going to stroll for a while," hikes. St. Mary Falls/Virginia Falls/and even Hidden Falls, and on the west side, Avalanche Gorge. You can extend the gorge to Avalanche lake if you feel good. You can also drive up to Polebridge and then Bowman Lake, and that'll kill a day very quickly
So maybe a longer hike like Iceberg, then the waterfalls, a longer hike, then Logan Pass for Hidden Lake, then a longer hike, you get the idea. Add beer or wine seasoning to taste.
Jay (remember me?) W