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).
YANKEE BOHO Deer Isle, Maine
Workshops, galleries, and lobster shacks proliferate in this fishing village-artists' colony. The wood-framed Pilgrim's Inn (20 Main St.; 888/778-7505; www.pilgrimsinn.com; doubles from $129) dates back to 1793.
EMBRACING NATURE Catalina Island, California
Use the dockside Hotel Metropole (Avalon; 800/541-8528; www.hotel-metropole.com; doubles from $159) as a base while exploring by horse, bike, or kayak.
BACK TO BASICS Vieques, Puerto Rico
The concrete design of Hix Island House (787/741-2302; www.hixislandhouse.com; doubles from $150) reflects the island's simple aesthetic: empty beaches and unfettered relaxation.
LATIN FLAVOR Isla Mujeres, Mexico
Brightly painted fishing boats and shacks line the shores of this island just 15 minutes from the crush of Cancún. Arrange snorkeling excursions from the waterfront Hotel Secreto (Punta Norte; 52-998/877-1039; www.hotelsecreto.com; doubles from $150).