I'll be in the area five days, and I'm planning to hike three. Past experience is after a longer day I feel like taking a day off. This is vacation, after all. My December plan is:
1. Cliff and Redfield from Upper Works. If weather or conditions are mediocre, I'll do Marshall instead.
2. Saddleback from Garden in Keene Valley. If things go well I'll go up Gothics, too. I've done Gothics before from the other side, and it was clouded in. It's supposed to have fantastic views. An alternate that day is Colvin and Blake. That hike is just as long but quite a bit lower. I still need Cascade and Porter, too.
3. Colden from the Loj. Cascade and Porter are good alternates, too. Or if conditions are spectacular, I might go for Dix from Round Pond or AMR.
My full list of remaining peaks is Marcy, Skylight, Dix, Gray, Basin, Colden, Redfield, Saddleback, Rocky Peak Ridge, Macomb, Hough, Marshall, Cascade, South Dix, Porter, Colvin, Grace, Blake and Cliff.
I've been trying to check off some of the trailless ones like the Santanonis, the Sewards and Allen. I've been pretty lucky with weather, but so far those have all gone really well. Couchsachraga is dumb because it's like a mile and a half each way from the Santanoni/Panther ridge, and it's so underwhelming. Allen seems to get some flack for being long for one summit, but the view of Panther Gorge is spectacular. Seymour, too, sits sort of by itself but has some great views near the summit.
I figure I need twelve good days to finish my nineteen. Are you trying to finish?