By Tracey Minkin
Since the late 1800s, Marblehead has been able to claim its title as yachting capital of the United States, counting six yacht clubs and the oldest junior yacht club in America. On any weekend, the harbor fills with the furled sails of regatta competition. Less than an hour from Boston, Marblehead boasts a highly educated population that has driven the town to maintain some of the highest-ranked schools on our list.
Where to Stay: Harbor Light Inn is sweet and romantic. Rates start at $145; 781/631-2186 or harborlightinn.com.