Since the time of Herman Melville, Nantucket has evolved. Instead of windswept remoteness, you'll find a vibrant, international neighborhood with some extremely chic accommodations.
The evening had begun in a rather harmless manner. I enjoyed dinner with my wife and two teenage sons on the patio of the Sister Ship restaurant at the Faraway hotel in Nantucket. In August, after a long day of sightseeing, we were ready for some quality time as a family. However, as the evening went on, the vigor and excitement increased as tanned, well-groomed, and glossy people sat in cane chairs and on yellow-upholstered sofas.
The Los Angeles-based pair seated next to us. After a few beers, they started chatting and identified themselves as being "in the movie industry." I would later learn that one of them had once been the president of a significant studio. A younger couple was seated at the table in front of us, and as they bent down to chat, we discovered that they were fashion entrepreneurs with outlets all over the nation. One of them was a well-known senator's daughter.
A few more people joined our group, and as the wine flowed and the music grew louder, we quickly discovered that we were a part of a global gathering that was primarily urbanites exchanging tales about their exotic travels. The atmosphere was characterized by a carefree, affluent cosmopolitanism that may have been imported from Manhattan, London, or Tokyo. At one point, I commented to my wife, "I feel like we're in the thick of a party," and she nodded in accord. The kids buried theirs deeper into their iPhones out of frustration.
To put it lightly, this was not the environment I had anticipated when we boarded the ferry in Hyannis Port, 30 miles across Nantucket Sound on the Massachusetts coast, a few days ago. In preparing for our trip, I had been reading "Moby Dick," and I had taken note of Melville's descriptions of Nantucket as "all beach, without a background," of "the innocence of the land," and of its "hermit" inhabitants. I was aware that the island had changed since then; its role as the center of America's whaling business, which lasted from the middle of the 1700s to about 1830, had been replaced by a new one in the second half of the 20th century as a playground for the affluent. Still, I was hoping for a tranquil getaway away from the distractions of modern life.
The air was warm when we arrived at Nantucket Harbor, making it almost easy to maintain such delusions. However, I started to understand that the island I had envisaged had been replaced by something very different as we wheeled our bags away from the port and through streets busy with rental motor scooters and visitors negotiating cobblestones in high heels.
The structures still had an old-world appearance, with unique white trim, sloping roofs, and cane porch furniture. The enterprises that were there, though, appeared to be invasions from the present (or, depending on where you live, the future). There were high-end stores, cool bars, and chic eateries. If Nantucket had once been a stronghold of the East Coast establishment, sushi, ceviche, and Tibetan momo had made it into the island's fortress.
The Life House, Nantucket, our hotel, which is a sibling property to the Faraway, felt very much like it belonged here. It had the coziness of an Airbnb and the services and amenities of a boutique hotel, and it was located in a two-story house not far from the town's core. We were shown into a sophisticated living area by a young staff member who was dressed in casual attire. The space had fine wooden floorboards, cabinets, and side tables that had been painstakingly repaired with a modern Soho House gloss (chill-out soundtrack and herbal scents in the air). Arriving at a hotel was more like going to a friend's residence.
My family and I spent the first couple of days touring Nantucket on the stylish white bicycles Life House provides free of charge to its visitors, hopping between formal lunches at restaurants with white linen tablecloths (much of the island's dining culture is formal) and leisurely afternoons on sandy beaches. We went back to Life House in the evenings and gathered around a fire pit in the courtyard as well-dressed staff members gave us chocolate and marshmallows to make s'mores over the fire. We were awestruck by the stars. It was quite similar to camping, but not at all.
I returned to Sister Ship one afternoon to meet Liz McDermott Barnes, an interior designer who had spent around 20 years vacationing on Nantucket before settling there part-time seven years earlier. McDermott Barnes highlighted the changes she had seen on Nantucket, including the influx of new money, the increase in home prices, and the chartered aircraft that brought a multitude dressed in all black even on the warmest summer days.
McDermott Barnes said, "Nantucket has changed," and I thought she sounded a touch nostalgic. She appeared to be relishing the modernization that was bringing it into the current day, but, at the same time. She added, "We have to keep this facility current. We must adapt to the times.
To demonstrate how tastes have changed on the island, McDermott Barnes offered to give me a tour of the town. We began with Sister Ship's bar, which bills itself as a "cocktail club" and is embellished with Moroccan arches, Chinese lanterns, Polynesian barstools, and Italian marble counters. She clarified that the décor was intended to reflect a sea captain's voyage across the world and that these seemingly random juxtapositions constituted a cohesive narrative.
After checking out, we strolled down Centre Street past eateries, shops, and sporadic real estate offices. As we walked, McDermott Barnes revealed to me that while her clients used to demand "historically relevant" designs, they are now more frequently choosing what she refers to as "transitional design," which combines the conventional with a more contemporary viewpoint.
She gave the hotel at 21 Broad as an illustration. Its outside was essentially identical to all the other structures in the city, with grey clapboards, white trim, and a shingled roof. This aspect is the result of strict planning regulations protecting ancient Nantucket's appearance. However, the 27-room hotel's interior was a very another scene, with sky blues, vibrant yellows, and fanciful furnishings with Art Deco influences—a New England interpretation of Miami Beach.
After passing the Whaling Museum, a former candle factory that has been transformed into a contemporary gallery for historical items, we continued down South Water Street, which is dotted with pizzerias, ice cream parlors, and pubs. I was sent to Sylvia Antiques by McDermott Barnes, a business that has been run by John Sylvia's family for three generations.
As she led me through his shop, Sylvia pointed me to pieces of art and shipping memorabilia from the 18th and 19th centuries while relating tales about their provenance and the parts they played in regional customs. The shop includes a sizable selection of "lightship baskets," so named because it is believed that sailors on ships that served as floating lighthouses weaved them. The intricate shell mosaics known as "sailors' valentines" were brought back from Barbados by returning sailors as gifts for their spouses. These things were once thought of as baubles, but on the new Nantucket, they were transformed into treasures and frequently sold for thousands of dollars.
I found myself enjoying Nantucket's most recent incarnation as we bid farewell to Sylvia and made our way back out onto the street. The town had a noticeable buzz, as well as an unexpected air of openness and accessibility. Nantucket was suddenly teeming with a diverse population, whereas admission was primarily confined to particular classes and races in the latter half of the prior century. One evening, we took an Uber and got to know Praveen Neupane, our young Nepali driver. He identified himself as a member of the island's year-round community of about 50 Nepali families, who were gathering support for a petition to erect a Hindu temple.
But after a few days, I began to crave the "innocence of the land" that Melville had spoken of and began to wonder what was beyond the modern city. My wife and sons agreed: we had traveled as a family in search of nature, solitude, and fresh air; now we questioned if we could still locate them.
This is how I found myself in a car with a local real estate agent one morning on our last day on the island. Her name is Holly Ruth Finigan. Finigan, a native of New Hampshire, had lived on the island full-time since 2005; before that, she had only visited during the summer. She volunteered to drive me about when I had called her and stated I had been staying in town and was curious to see a more tranquil side of the place. She admitted that "the summer season might feel daunting." The population of Nantucket varies significantly between January and July.
Like McDermott Barnes, she talked about how her adopted home had changed as we were leaving town. She proclaimed, "Social media blew up Nantucket." It is the most picturesque island, according to Instagram. She acknowledged that the feeling of isolation she experienced during her first visit was becoming more elusive, but she argued that it was still present. She said, "Nantucket is a choose-your-own-adventure," as we drove through a wide open area of land known as the Serengeti by locals. There are sporadic glimpses of the glittering ocean beyond it.
I quickly discovered that we were traveling to Siasconset, also known as "Sconset." This former fishing village, which sits on the eastern side of the island and has a year-round population of fewer than 100 people, is a maze of grassy lanes that wind between charming homes and gardens brimming with roses and dahlias. A post office, one grocery shop, and the Siasconset Casino, a club with immaculate red clay tennis courts, make up the village's central business district. 'Sconset was "a step back in time," according to Finigan. It made me think of the English Cotswolds.
We traveled the two miles of the "Sconset Bluff Walk," a dirt path that carried us 50 feet above the Atlantic Ocean and gave us a view of the ocean's never-ending peeling waves. Some of the homes lining this cliff date back to the 17th century; they were like antiques battered by the sea wind, an odd blend of dilapidated and opulent.
According to Finigan, the village's name is derived from the Wampanoag language and approximately translates to "a site of big bones." Ship captains and their families used to flock to the village during the summer to escape the odors produced by the whale-processing facilities in the main town during the late 1700s and early 1800s.
Standing on that bluff, I pictured those old houses as bones, tangible reminders of this place's past. Finigan continued, pointing along the shoreline at a scene that had mostly withstood the test of time, "There are all these old souls in this place." She said, "You can still find bits of heaven on Nantucket," and I had to concur.
Knowing Where to Stay Far Away in Nantucket Nantucket: This 62-key property's colorful and entertaining design was motivated by the exploits of an idealized female ship's captain.
The Life House, a boutique hotel in a Federal-style mansion from the 19th century, opened its doors in 2020. With floral tiles, rattan writing desks, and pops of color all over, the aesthetic is light and airy.
A Relais & Châteaux establishment with access to the ocean and solitude is The Wauwinet.
The 27-room 21 Broad is a chic, unpretentious option in the center of downtown, blending in with the other clapboard houses in the area.
Where to Eat The Chanticleer: This well-known island favorite is located in the sleepy village of 'Sconset and serves traditional French fare including halibut à la provençale.
a Club Car This seafood restaurant, housed in a vintage train carriage, is renowned for its weekly live piano performances.
Sister Ship: Visit for the seafood from the Mediterranean and stay for beverages in the courtyard, where the party frequently lasts until the wee hours of the morning.
Topper's: This elegant restaurant at the Wauwinet features a long wine selection and a refined atmosphere while overlooking Nantucket Bay.
Spend the day at one of the island's most tranquil stretches of sand at "Sconset Beach" (and watch for seals surfacing above the waves). Gully Road 7,
Browse a wide selection of traditional New England items at Sylvia Antiques, including folk art and traditional baskets.
The whaling museum, located two blocks from the ferry, provides a thorough overview of Nantucket's history as the nation's whaling capital.
Under the headline "Summerland," a version of this article first appeared in the August 2022 issue of Travel + Leisure.