Maine is a great place to charter. Yes many of the boats in the charter fleets are older as this is the Maine style. You won't see to many Hunters or Beneteaus up here. There are quite a few Catalina's, Sabre's, Tartan's etc. but less of the Carribean charter style boats. The two best places to do a charter are through Hinckley Yachts or Morris Yachts but they are expensive. All of the charter fleets in Maine are privately owned yachts not like the SunSail or Moorings deals. Some boats are spotless some are fair but they all sail! Even if you get a fair boat you'll forget it quickly once you take in the scenery.
I'm an amature photographer and have an entire photo gallery dedicated to sailing the Maine Coast. Feel free to check it out. If you have any questions feel free to ask away. Behind each of the thumnail photos on my web site are galleries have fun.....
Maine Coast Sailing Photo Galleries
http://www.pbase.com/mainecruising
Lobster Baking on Hells Half Acre Island in the Deer Isle Archipelago.
-Halekai