nantucket lighthouse and view of the beach- wineries and beyond

Nantucket Three Ways: Wine Festival and Beyond

Carrie Ohlandt -

Art and Culture

For most travelers, “Nantucket” represents an idea more than a place. It’s a shade of red, a crisp aesthetic—the very word connotes exclusivity. Nantucket is an island in both geography and personality, remote enough to preclude Cape traffic and expensive enough to keep more pedestrian visitors on the mainland. Underneath those preconceptions, the real Nantucket is an inviting, sophisticated destination that travelers must experience for themselves to fully understand. The island’s most carefully guarded secret is that it’s really not so guarded, after all.

Nantucket often shares a frame with Martha’s Vineyard, a sister island off the coast of Massachusetts. But moreso than the Vineyard, Nantucket’s bustling town center invites weekenders and day-trippers to dine, shop and take in the casual sophistication that abounds. Locals are protective: You’ll see “Twenty is Plenty” (as in, miles per hour) and “Gut fish, not houses” signs around the community. One evening bike ride to enjoy starlight on the beach, and you’ll see why—There’s no light pollution for miles.

Each May, the island comes alive during the Nantucket Wine Festival, a five-day exhibition of local fare and wines from around the globe. Vintners, sommeliers, authors and connoisseurs descend on Nantucket for a robust slate of receptions, tastings and dinners where the destination is the star. This year, Wine Festival starts May 17 and concludes May 21, kicking off the high season in America’s most storied vacation colony.

Three properties in the Select Registry portfolio offer three distinctive takes on the island—choose your own adventure.

For Romantic Sophisticates

Like many properties on and off the New England coast, Union Street Inn observes a strict April to October season—and travelers don’t want to miss it. Innkeepers Ken and Deborah Withrow parlayed decades of hospitality experience (including time at NYC’s famed Algonquin) into a boutique property where impeccable service is the signature. Union Street Inn expertly tailors the guest experience to each visitor’s preference—if you’re searching for discreet, hotel-style interaction with staff, it’s yours. If a personalized, B&B style approach is to your taste, Withrow’s team will make it happen. It’s no wonder the property rated among TripAdvisor’s best small hotels (Travelers’ Choice). Union Street Inn offers “the real Nantucket, not a guidebook Nantucket.”

Three years ago, a renovation by Trudy Dujardin updated Union Street Inn’s crisp, French-inspired aesthetic (The pristine interiors are also a credit to Deborah’s background creating store displays for Bendel’s on Fifth Avenue). Ken says the island’s proximity to urban centers makes it approachable—especially as guests become younger and more affluent.

“Nantucket was always an interesting, sophisticated island,” Ken says. “You’re not in the middle of the South Pacific—you’re close enough to Boston and New York.”

Select Room: Union Street Inn’s best guests are couples on a romantic getaway, and suite #9 boasts a fireplace, wet bar and four-poster king bed. Its corner location lets in plenty of light.

On the Town: Ken recommends Straight Wharf for seafood. For dinner and drinks, Greydon House is a Nantucket showstopper: Michelin star chef Marcus Gleadow-Ware serves a progressive take on American classics while mixologists pay tribute to the island’s maritime past. The Greydon’s Cup contains Absolut Elyx, banana, coconut, lime and champagne—and the lounge is gorgeously hip.

For Understated Elegance

Casual elegance rules the day at the Brass Lantern Inn, where returning guests enjoy the pet- and family-friendly atmosphere. Innkeeper Michelle Langlois established the property in 2000, and describes her approach as “gracious but not stuffy.” Visitors can’t miss the scent of hydrangea or the New Dawn roses climbing all the way to the roof.

Over the past three years, the Brass Lantern has been completely renovated from top to bottom—all guest rooms and common areas and, this year, the garden and patio. The firms, Fenwick House Design and Nantucket Looms, have brought this stately building with 17 guest rooms into today’s Nantucket style with soft greens and pale taupes and greys in upholstery with walls offset by sparkling white trim.

Start the day with a “continental plus” breakfast of homemade granola, fresh fruit and French press coffee, then see what’s happening at the Athenaeum.

“It’s a spectacular heartbeat of the community,” says Michelle. “They stage workshops and plays, screen classic movies and more. And it’s architecturally significant…it looks like a Greek temple from the exterior.”

Select Room: From the Brant Point Room (each is named after a whaling ship), guests can hear the ferry leaving each morning at 6:30. The luxurious space gives guests the feeling of being out at sea.

On the Town: For lunch, swing by the new Corner Table for sous vide flank steak or a fresh Cubano sandwich. Michelle recommends Company of the Cauldron for dinner and drinks on the harbor at Galley Beach for amazing boat watching.

Innkeeper Matt Parker made his first voyage to Nantucket almost 50 years ago, and has operated Seven Sea Street Inn since 1987. The property’s red oak post architecture exudes the ambiance of a coastal lodge. After a cozy breakfast in bed, stroll down Main Street and peruse cooking class offerings at Nantucket Culinary Institute. Wine Festival is not the only week of the year when visitors can learn about flavor and balance on Nantucket.

A hallmark of Seven Sea Street is the collection of local art on display throughout the inn. A variety of mediums capture the splendor of Nantucket: supple watercolor seascapes and earthy oil tributes to sailboats and whaling vessels. These works by Deborah Sosebee enhance the mood of guest rooms and integrate all elements of the island—and if you like something, you can buy it right off the wall.

Travelers can explore those sea, land and town-scapes for themselves: Nantucket is home to the Coskata-Coatue Wildlife Refuge, the Nantucket National Wildlife Refuge and other conservation sites where natural habitats have been preserved for generations. With a bike and a map, it’s all ripe for exploring—just don’t forget a water bottle. After a day of adventuring, kick back on Seven Sea Street’s unique roof deck.

Select Room: The deluxe queen suite offers cathedral ceilings and a private Great Room—complete with a kitchen, dining area, and a Vermont Castings gas stove. It may be ornamental through the summer, but for off-season travelers, it’s a comforting heat source.

On the Town: Matt recommends Dune, a modern chic meets casual comfort spot on Broad Street. For craft cocktails, stop into Òran Mór for a Beach Blanket Bingo: cold brew coffee, rum, coconut milk and cardamom bitters.

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