Order cocktails by the number
Jenny Benzie, master sommelier at local wine shop Épernay and full-time Nantucket resident of 3.5 years, said the best cocktails on the island are a toss-up between The Nautilus, which has Fernet on tap (yum), and The Proprietors, where "some cocktails are actually healthy." We’ll just take that at face value and order a few rounds… which you can do here by the number, not the name, if you want to sound like a local. If you want to have a drink by the water, Benzie recommends CRU Oyster Bar, where you can pair "perfectly chilled rosé" with crab cocktail, a warm buttered lobster roll, and chocolate pôt de creme for dessert. Go around 3pm, and you’ll be hitting the perfect time for a little seaside breeze.
Drive across the beach
Forget the flip-flops; you’re crossing Great Point Beach with four-wheel drive. Korin Matter, general manager of 21 Broad and full-time Nantucket resident of three years, recommends renting a Jeep to drive across eight miles of beach on Nantucket’s lesser-explored eastern shore. The terrain is 50% conservation land, and makes a peaceful respite from the summer madness. Matter recommends taking a day for the trip: pack a picnic, paddleball, and sunblock, and hit the sand.