Day 2 plan is very ambitious, but maybe doable if those are close enough together and it is a slow day everywhere. You may have to wait 45 minutes to an hour for your assigned group to be full and a guide available, so be prepared for that. You may want to hit your preferred stop (or the one you anticipate to be busiest) first so you get there early in the day before crowding increases your waiting time.
Last year we hit Makers and Woodford. Both were great, but we liked Woodford better. Makers tour gave a better historical perspective, but you'll get a big dose of that everywhere. We chose those two upon the advice of friends who had done much of the Trail the year before. We had lunch at Makers when we were there. It is a beautiful area of the country. The horse farms are amazing.
Samples are included (everywhere, I think)--looked to be about half an ounce (maybe slightly more) of 5-6 samples with different products. The tastings are done just before you exit through the gift shop.