5 Things to Do in … Nantucket

The small island offers big charm and lots of cool things to do, from strolling cobblestoned Main Street to pedaling along the beaches. PEOPLE photo editor Regan Stephens shares her top picks for maximum fun


Located on the Island’s Northeast point, The Wauwinet has a refined yet relaxed vibe, with a lush, lounge chair-dotted lawn that reminds me of The Great Gatsby. Have lunch or dinner at the Inn’s award-winning restaurant Toppers, and be sure to reserve a complimentary, one-hour ride there via water taxi. When choosing your mealtime, consider these scenarios: tucking into the freshest plate of oysters (seriously – they're harvested 300 yards from the property) on the restaurant’s deck overlooking Nantucket bay for lunch, or savoring a glass of bubbles on the boat – the evening cruise offers cocktail service – before dinner in the elegant dining room. Either way, you win.