This Former Sea Captain’s Home Is Nantucket’s Most Stylish Boutique Hotel

Credit: Tim Williams

The enchanting island of Nantucket has been a storied playground for the elite for decades. Located 30 miles off the south coast of Cape Cod in Massachusetts, it was once considered the whaling capital of the world in the 1880s and continues to draw a fiercely loyal crowd these days — although they may look slightly different than the weathered fishmongers who first called Nantucket home.

Credit: Douglas Friedman

With ten pristine beaches, clusters of cobblestone streets flanked by hydrangeas, and grey-shingled Quaker cottages aplenty, Nantucket, or “ACK” as the locals call it, is idolized for its charm. Not to mention its abundance of restaurants and boutique hotels. One, in particular, stands out from the rest: Greydon House.

Credit: Douglas Friedman

Fittingly, Greydon House was the former home of a sea captain and arguably has the best address in town, at 17 Broad Street. Walkable to everything, including the Wharf, it’s well-positioned and beguiling on every level. 

Credit: Douglas Friedman

Upstairs, 20 well-appointed guest rooms and suites beckon. Each is meticulously designed by Roman and Williams of the Ace Hotel New York and The Standard, High Line fame. Furniture is sourced from Morocco, Portugal, and China; modern and old-world elements are juxtaposed, and pendant light fixtures cast a soft rippling effect resembling the tides. The beds are also sumptuous, swathed in Indian-inspired, block-printed linens by John Robshaw. 

Credit: Douglas Friedman

Although the accommodations vary in terms of found treasures within — a 19th-century French bamboo table resides in one corner of a room; a vintage Danish Kaare Klint safari chair in another — a few key details remain the same: organic kilim rugs, Napoleon III antique mirrors, and Nordic oil paintings of seascapes. 

Credit: Douglas Friedman

Then there are the bathrooms. Of all the impressive elements that went into the loving restoration of this hotel, the bathrooms are, by far, my favorite. Behind each shower curtain, you’ll find a mural depicting maritime adventures comprised of white and blue, hand-painted Portuguese tiles. The Grown Alchemist and Ursa Major skincare products are a bonus to a shower experience you’ll never want to end.

Credit: Douglas Friedman

The ground-floor library is a beloved nook as well. Rows of shelves are lined with boat replicas, Jacques Cousteau tomes recalling ocean tales, and beautiful books showing off America’s famous gardens. Cushy sofas are clad in variegated ikat, and nautical nods play off the island’s whaling history. 

Credit: Daniel Schwartz

Around the corner is Via Mare, their whimsical Italian restaurant inspired by Venetian bacaris, or spirited drinking tavernas serving small bites. The best seat in the house is behind the bar, though, to catch a glimpse of the property’s most prized artwork: paneled scenes of Chinese merchant ports by painter Dean Barger. 

Top Takeaways

Location: Nantucket, Massachusetts

Star Rating: Four-Star

The Vibe: A former sea captain’s home-turned-boutique hotel filled with objets d’art and worldly treasures in the historic district.

Our Favorite Thing About the Hotel: The above-par seasonal packages. Embark on a sunset charter aboard Captain Mat Barker’s 1930s sailing yacht, The Blue Peter, with lobster rolls and rosé; take part in a Lavender Farm Wellness retreat with private yoga sessions and guided forest bathing, or enjoy stargazing in December, when the Geminid Meteor Shower peaks. With almost zero light pollution 30 miles out at sea, Nantucket offers some of the best stargazing in the states.

Food + Drink: Via Mare is Greydon House’s on-site Italian restaurant from the owners of Ventuno and Pizzeria Gemelle, featuring numerous dining rooms, a living room-cum-bar, and a porch.

Any Neighborhood Recs? Bar Yoshi in Old South Wharf for sushi, yakitori, and udon noodles, plus their more casual concept O Bar, for oysters and raw bar specialties across the seashell-crusted street. Also, Wharf-adjacent is CRU. This lauded mainstay is the island’s #1 hotspot, but the food lives up to the hype — as do their lobster rolls (served warm or chilled). For something different and extraordinary, reserve a table at Sister Ship: an elevated Mediterranean-inspired restaurant with a killer cocktail list (try the chartreuse-hued Faraway Mermaid). However, no trip to Nantucket is complete without a stop at Lemon Press for breakfast, Millie’s for tacos, and Cisco Brewers for craft beers, food truck eats, and good times.

Amenities: Concierge; free WiFi; Grown Alchemist & Ursa Major Skincare products; complimentary beach chairs, Lands’ End totes, and Fujifilm instant cameras.

What’s Nearby? Nantucket Whaling Museum, the ferry terminal, The Chicken Box, Michael Kane Lightship Baskets, Juice Bar (beware of the line down Broad Street for their famous ice cream), Brant Point Lighthouse, Steps Beach, and Jetties Beach.

Rooms: 20

Pricing: Room rates begin at $440/night.

Closest Airport: Nantucket Memorial Airport (ACK). Pro tip: Skip the 4+ hour drive and 1-2 hour ferry schlep to the island and fly Tradewind instead. The private airline has 25 flights daily from the New York area and only takes 45 minutes from gate to gate. 

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