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;; 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;; 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

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;; doubles from $129) dates back to 1793.

EMBRACING NATURE Catalina Island, California
Use the dockside Hotel Metropole (Avalon; 800/541-8528;; 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;; 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;; doubles from $150).
—David Kaufman

The Pearl

One of three Nantucket restaurants operated by Seth and Angela Raynor, this cool, modern space focuses on coastal fare with an Asian twist. White and blue tones, exposed brick, and aquariums set the tone inside at this downtown location. Helmed by executive chef Seth Raynor and chef de cuisine Liam Mackey, The Pearl utilizes locally-sourced seafoods for dishes influenced by the journeys of the chefs. Start with duck confit bao with cucumber pickles and pears and continue with an entrée like the green Thai coconut curry, prepared with tofu and pineapple.

Hotel Secreto

Custom built in 2001, the Hotel Secreto is not signposted, yet it is one of the best-known accommodations on the five-mile-long Isla Mujeres. The white cube-like hotel is laid out with just nine quiet guest suites, where luxury touches include day beds on the expansive balconies, floor-to-ceiling glass, and stone floors. All also include wireless Internet, air-conditioning, and a selection of bottled wines. The property also includes a fitness room, shaded patio (a perfect place for sipping cocktails), and sun loungers positioned around the 20-meter lap pool, which faces out toward the beach and ocean.

Hix Island House

With its 13 highly stylized, all-concrete (yes, concrete) rooms that seem to have sprung from the surrounding woodland, this hotel is a world away from most other lodgings in Puerto Rico. It's the brainchild of Canadian-born architect John Hix, whose focus on the natural environment led him to create the open, three-walled rooms (with steel garage doors to pull down at night). The décor is minimalist, with mosquito-netted beds; concrete slabs serving as tables and shelves; and kitchenettes with small refrigerators and stovetops. Eco-travelers will feel at home here: the units are partially solar-powered, and water from the kitchens and outdoor showers is recycled for the on-site gardens. The grounds include a beautifully designed pool and pavilion where yoga classes are (naturally) run daily.

Hotel Metropole

Centrally located in downtown Avalon, and within walking distance of the beach, this upscale hotel is a mix of guest rooms and mini-suites, plus its two-bedroom Beach House. Accommodations in the VIP wing come with a water view and extras like whirlpool bathtubs and fireplaces. The look throughout the hotel is high-tone island, with light-colored walls, contrasting wood trim, and beachside touches like plantation shutters and billowy drapes. On-site there is a day spa as well as the Metropole Marketplace, a cluster of shops and services (like a nail salon and laundromat) that are open to the public.

Pilgrim's Inn

Built in 1793, this landmark inn on Northwest Harbor is on the National Register of Historic Places. It has since been restored, but original details like exposed wooden beams have been kept intact, and an old-school aesthetic still prevails. Each of the 12 rooms has a private bath and is uniquely decorated with country-time accents like flowered bedspreads, comfy armchairs, and, in some rooms, working fireplaces. Three cottages have more space with kitchenettes and private decks. Breakfast is included in room rates, and the inn's Whale's Rib Tavern serves dinner and cocktails.

Veranda House

A circa-1684 manse with three wraparound porches with views of the harbor; the concierge will arrange day trips to the beach of your choice (we suggest the nearby and secluded Madequecham).