Nantucket Island, Massachusetts: The Wauwinet Hotel

  Stay: The Wauwinet Eat: Toppers Drink: Wauwinet Lawn Bar Do: Walk Great Point Beach search for seals    

St. John, US Virgin Islands

  Stay: Caneel Bay, A Rosewood Resort Eat: Sugar Mill Caneel Beach Terrace Drink: Caneel Rooftop Beach Bar Do: Virgin Island Ecotours Hang out on Caneel Bay’s seven beaches Take a painting class