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I've sailed a few times with the Wooden Boat School out of Brooklin Maine. They had a Herreschoff ketch on loan and we got to sail it daily for a week. (Herreschoffs are to boat nerds what Ferraris are to car dorks). The other time I took a class called Craft of Sail and we sailed a different boat every day.
The school fed us great food and the sailing is top notch. 5/5 Would recommend to anyone with a week to spare on the East coast.