GET THERE: The preppy coastal playground is about 80 miles southeast of Boston.
STAY: 76 Main is a just-opened 20-room hotel in the heart of town. Vineyard Vines even designed a suite—the pillowcases are made from board shorts, and the window-shade edgings are crafted from belts. (From $309; 76main.com)
CHEAP THRILL: The beach! The hotel has beach bags and chairs you can borrow for your excursion to the shore, which is about a five-minute walk away.