"While Shelter Island was originally a favorite summer retreat for old-money families and notables like Marilyn Monroe, Arthur Miller, and the Kennedys, hoteliers are now turning the tucked-away island into a year-round destination. The Chequit, owned by the same family that recently reopened Peconic Bay Vineyards, reopened last summer after a two-year renovation—just in time to celebrate its 150th anniversary. The hotel’s makeover includes a luxe update to its existing 19 guest rooms, an addition of 16 more, plus a revamp of their famed restaurant The Tavern, now overseen by chef Darren Boyle, formerly at Salt, another notable restaurant on the island. Two new food concepts were also introduced: Weakfish, specializing in New Asian cuisine and Asian-inspired cocktails; and Heights Café, which offers coffee and pastries until mid-afternoon."