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The islands off the coast of Massachusetts have long been synonymous with Old Guard summers, but a younger generation of trendsetters is breathing new life into Nantucket. Victorian bed-and-breakfasts share cobblestoned streets with a clutch of hip boutiques, restaurants, and hotels. This season, New York-based shoe designer Vanessa Noel—who opened VNH (5 Chestnut St.; 508/228-5300; www.vanno.com; doubles from $340), the island's first boutique hotel—will spotlight fanciful accessories by Lana Marks and Mish, among others, in her lobby store. At the Pearl (12 Federal St.; 508/228-9701; dinner for two $125) the signature yellowfin tuna tartare with spicy crème fraîche is the ultimate dinnertime fix. If it's fresh air you're after, rent some wheels at Young's Bicycle Shop (6 Broad St.; 508/228-1151; from $25 per day) and start exploring—many of the best beaches are only a couple of miles out of town. STAY The 20 rooms at the gingerbread-trimmed Veranda House (3 Step Lane; 508/228-0695; www.theverandahouse.com; doubles from $199) are furnished with Frette linens and Simon Pearce glass lamps. DON'T MISS Constellation tours with astronomer Vladimir Strelnitski on Mondays and Fridays at 9 p.m. in the Loines Observatory (59 Milk St. Extension; 508/228-9273).
—Jaime Gross
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