Shopping in Nantucket Town has gotten almost unrecognizably chic over the past few years. A pair of stilettos isn’t the obvious choice for tackling the island’s cobblestone streets, but women who must have a new pair of Jimmy Choos (or a Brioni blouse or Ferragamo handbag) can swing by David Chase. Fancy undies—Cosabella camisoles, Natori chemises—are right around the corner at Ladybird Lingerie. And shelter-shop hounds who can’t live without another John Derian découpage plate or embroidered Ankasa throw pillow should visit Trillium.
Once you’re done shopping, absorb the season’s last rays at one of Nantucket’s justifiably famous beaches. Sheltered north-shore strands like Jetties and Children’s Beach are within walking distance of town. (Jetties is much bigger and has a casual sit-down restaurant with great clam chowder.) Surfers should head to wilder southern-coast beaches like Surfside, Miacomet, and Cisco, though there’s limited parking, so arrive early on big-swell days. To the far southwest are the windswept dunes and spectacular sunsets of Madaket; bring a blanket and a bottle for sundowners among local families.