Channel Your Inner WASP In Nantucket
This little island off of Cape Cod, Massachusetts is a prepster's dream. Bike around the quaint town for #OOTDs in front of the cedar-shingled homes bursting with colorful hydrangeas, take in the sun at the beaches with lighthouse views, and fill up on unmatched quality seafood. Nothing beats a stay at The Wauwinet, which just debuted a new private cottage, called The Anchorage House, designed by Serena & Lily.
[Photo via @georgiemorley]