We did a Trek Travel weekend tour for our first foray into bike touring about 10 years ago. We chose it, basically, because we could drive there, and use our own bikes. As Veronica said, be prepared for very steep climbing, the rest rolling, but beautiful scenery. On our tour, I did skip the climb over Mt. Mansfield, mostly because it was drizzling, the climb was 4-5 miles, and I was scared on the descent. I got in the van, as did many others. I might still skip this one if it was wet, but not if it was dry.
Last fall, we did a semi- supported inn to inn tour, in that a company planned our trip, gave us the routes, and carried our luggage. We rode alone, and there was no van support. If we really had a terrible issue, then, I believe someone would have picked us up tog et to a bike shop. We loved this option, as there were no other personalities to deal with, we are quite competent with a GPS, and the places we stayed were all unique and the restaurants awesome. The last day was rainy, about 48 degrees, with really hard climbs. It was one of those you might get a divorce over this moments, but, we did it. I would not recommend Vermont if you only can train on flat roads.
2015 Trek Silque SSL
Specialized Oura
2011 Guru Praemio
Specialized Oura
2017 Specialized Ariel Sport