My father went on a "booze cruise" on the True Love on Seneca Lake.
http://www.schoonerexcursions.com/index.htm
It's a classic John Alden-designed Schooner dating from the 20's.
Looks delightful. He reported that it was well-maintained and well-handled.
The well-handled, lead me to start looking at a Coast Guard Captain's License. Specifically the "6-pack" license or "OUPV license". http://www.seaschool.com/oupv.htm. Practical Sailor is looking at the on-line training alternatives that have arisen.
The book-learning part is challenging, but manageable. The deck service time, however, might be difficult. They require 360 days of "total boating experience", which I may have accrued since taking my first classes back in '97. Or I may have to wait a year or so and accumulate deck days on Red Ranger.