Nantucket is an island nestled off the coast of Massachusetts that is steeped in rich maritime history. Its peaceful cobblestone streets wind their way through charming neighborhoods. And of course, beaches and water activities can fill your day. It is an easy flight or ferry ride from the Boston/Cape Cod area.

Nantucket’s Rich Maritime History

The Nantucket Whaling Museum is a large, fascinating museum that provides a great introduction to Nantucket. , the primary branch of Nantucket Historical Association. The museum goes way beyond whaling to examine Nantucket’s geological, human, religious, economic, and cultural history.

The museum tells the island’s history through a film, regular presentations, and exhibits. It houses a 48-foot teenage whale skeleton (full grown Sperm whales can grow to up to 80 feet long and weigh 60 tons), a whaling boat, a large Fresnel lighthouse lens, hundreds of pieces of scrimshaw and dozens of Lightship baskets that whalers carved and wove, and all types of mementos from their trips and artifacts from their homes.

The Crucial Importance of Whales

Nantucket was first settled in 1659 and became the world’s largest whaling port and one of its most wealthy and progressive towns in the 18^th-century. The whale oil industry eventually crashed (primarily due to competition from petroleum), throwing the island into a deep depression until the beginning of the 20^th century.

Nantucket was originally  created as a glacial moraine 20,000 years ago, and was separated from the mainland by rising sea levels. Prior to 1659, when the first Englishman arrived, it was home to 5,000 Wampanoag Indians who helped the handful of settlers (about 100 families by 1700). Although the island’s resources did not support the settlers initial occupations (faming and sheep ranching), the Indians taught the settlers how to salvage “drift whales” (dead whales that drift onto the beach). This led to the realization that the large British ships could be used to actively hunt life whales, rather than wait for providence to wash them onto their shores.

By 1670, they began hunting Right Whales (large baleen whales). Then they discovered that sperm whales yielded a particular prize—an oil that remained liquid when it got cold and that burned cleanly with no smoke or odor. It was a perfect lubricant to keep the wheels of the Industrial Revolution turning and to produce candles to light houses.

Initial whaling hunts were limited to one or two whales, since the whales had to be brought back to port and the fat rendered from them within a couple weeks to prevent spoiling. To address this challenge, innovative “tryworks” were introduced – brick ovens on board ships to process blubber into oil. The rendered oil could be stored in the ship’s holds for extended periods, even for years.

This advancement transformed whaling into a global enterprise. Whaling ships could now embark on multi-year journeys to explore all corners of the world, and return only when their holds were filled with valuable whale oil.

In 1711, a Quaker preacher arrived on the island and converted many of the island’s residents into a community that embraced gender equality. As a result, men could leave home for three to five years at a time leaving women to take on various responsivities including fiscal, commercial, and domestic duties.

Whaling = Prosperity

By the 1820s and 30s, Nantucket had established a virtual monopoly on the production of Spermaceti oil and more importantly, candles. This not only created a huge business, but also a highly profitable one with astronomical margins, especially for candles, which were much more profitable than selling oil.

The wealth transformed the island. Beautiful mansions were built. Nantucket’s highly cosmopolitan, free-thinking and well-travelled population collected mementos from around the world. Frederick Douglass made his first major public address here that inspired world-class scientific achievements, literature, and civil rights movements. Highly successful businesses transcended the whaling industry and that survive even today. Among the town’s first families, members ventures beyond Nantucket’s shores to make their mark. A Macy moved to New York and established a well-known a department store and a Folger moved to San Francisco to create a famous coffee company.

Some of the island’s women were as accomplished as its men. Maria Mitchell, for example, became the first and only woman admitted to the American Academy of Arts and Sciences for almost 100 years, and as a professor at Vassar College. Lucretia Mott became one of the country’s most prominent abolitionist and women’s rights and suffrage advocates. A descendent of the original Folger family became the second female medical doctor in the country.

The Challenges of Success

The island’s prosperity, however, had its downsides. The harbor area where the ships came and went and most of the factories were located, were filthy and emanated a horrible stench. And then there were the hundreds of sailors who came off of the ships that spent 2-5 years on the lonely sea with only scrimshaw carving to keep them occupied. With pockets full of money from their share of the voyages profits, and many far from their homes, they were looking for something to do. Many of the harborside streets contained wall-to-wall bars and brothels—a recipe for drunkenness, sin, fights, and muggings. Their activities were somewhat at odds with Quaker sensibilities and atmosphere for bringing up children—especially boys who ended up on whaling ship crews. But certain compromises were required in return for the wealth generated by the whale oil the ships carried in their holds.

Nor did the Wampanoag fare particularly well. Indians were subjugated as deckhands on ships, succumbed to English alcohol, and eventually (by 1800) died off from foreign diseases (especially Yellow Fever). This cheap labor supply was rapidly replaced by African-Americans (including some in the egalitarian Quaker meritocracy that eventually became whaling ship captains), Portuguese immigrants (from whaling ship stops in Cape Verde and the Azores), and Pacific islanders (from stops in the Pacific). The entry-level sailors led a tough life . They fulfilled hard, dirty, smelly, and dangerous work in cramped quarters and low wages of 1/150^th-to 1/200^th of the voyage’s net profits. Yet the captains and senior officers led comfortable and privileged lives and profited handsomely, with captains often earning about 1/10^th to 1/12^th of voyage’s net profits.

The End of the Whaling Era

A number of factors combined in the mid 1800s to change Nantucket. The commercial whaling industry was decimating the whale population. The Great Fire of 1846 that was fueled by whale oil stored on Straight Wharf, took out about a third of the town. The California Gold Rush drew men and whaling ships away from Nantucket to San Francisco. Many men never returned after fighting in the Civil War. But the most far-reaching issue was the discovery of oil and the refining of kerosene which substituted whale oil in lights. Nantucket’s population fell from 8,800 to 3,200 and the island fell into a 30 to 40 year period of economic decline.

Nantucket’s Reinvention as a Historical and Artistic Haven

This decline, however, laid the seeds for the island’s reinvention. With limited resources to construct new buildings, many existing structures fell into disrepair but were left standing. The island’s leaders turned this to its advantage by turning the island into a historical destination. It established the Historical Association in 1894, created an historic museum, renovated buildings, and promoted tourism.

Buildings were renovated and by the 1920s Nantucket was home to over 800 renovated 19^th-century buildings–more than any port town in the country. And artists, drawn by a combination of the island’s exquisite scenery, good light, and very cheap, rundown homes, moved in and created an important art colony.

The combination of the scenery, the art, and a prescient Nantucket Historical Association program to position the island as a historic tourist destination, began drawing ever larger number of increasingly wealthy summer tourists. These vacationers renovated and built million-dollar cottages, multi-million dollar homes and multi-multi-million dollar mansions.

“Affordable” summer homes cost only $2-6 million, and apartments may rent for as little as $6,000 per month. And then there are the “mansions” that go for $15-60 million for a place that is typically occupied only a couple months (especially July and August) per year. All of this is on what is essentially a continually eroding large sand bar that is widely expected to disappear beneath the waves in fewer than 350 years!

But that’s enough history. Let’s explore this fabulous island.

Exploring Historic Nantucket Town

Nantucket Town is the historic center of the island and the site of hundreds of pre-civil war buildings. It maintains much of its traditional charm with its cobblestone main street, narrow side streets, and beautifully restored 18^th and early 19^th-century homes. And if you are looking for real history, you need to look no further than the handful of 18^th, and even a couple of 17^th, century buildings.

The best way to see and learn about the most historic town buildings and is by taking a Nantucket Historical Association walking tour. Another way is to just wander.

• In 1881, Eliza Barney created a narrow-gage railway running from Nantucket town to Siaconset (“Sconset”). While it was certainly valuable in transporting supplies, the railway, and the Barney-owned hotels along its route, were instrumental in opening the island to tourists. It went out of business in 1917, the year after automobiles were allowed on the island. One remnant of the line remains: a club car that is now integrated into the Club Car restaurant.
• The Rotch, or Counting House Building is a 1772 structure whose shell survived the massive 1846 fire. It now stands as the oldest remaining commercial structure in the center of town. It served as the offices and warehouse of William Rotch, a wealthy ship owner and was one of the most interesting characters of Nantucket’s whaling era (see below).
• The beautiful, neo-classical Nantucket Atheneum (now a public library) was one of the town’s primary research and cultural centers, serving as a library, a concert venue and lecture hall, featuring speakers including Henry David Thoreau, Ralph Waldo Emerson, Horace Mann and escaped slave, author and abolitionist orator, Frederick Douglass. So important was the institution that it was the first public building to be rebuilt after the Great fire.
• The Pacific Bank, a pretty building that served under the direction of William Mitchell, who was also a noted astronomer built an observatory atop the 1818 brick building.
• A block on Center Street, known as Petticoat Lane, was a commercial street whose stores were all owned and managed by women who cooperated to align their businesses in ways that would not compete with each other.
• The Quaker Meeting Hall was built in the late 1838 to accommodate the island’s rapidly declining Quaker sect (which lost favor as a result of its pacifism during the Revolutionary War and the War of 1812). It was the site of regular meetings that were instrumental in shaping and defining priorities of a town ruled by Quakers from about 1700 to 1830.
• The grand mansions on upper Main Street built by the Quaker whale oil barons who overcame their religion’s prohibition to extravagant displays of wealth. These included the Coffin neighborhood, where the family built three identical brick neo-Classical mansions for various family members, and the twin neo-classical Hadwen buildings, which is now owned by the Historical Association.

A Supplementary Nantucket Historical Tour

Since the walking tour took us to only two of the Historical Association’s five historic sites (in addition to the Whaling Museum), we visited four others n our own.

• Greater Light. Two wealthy Monaghan wealthy, eccentric and religious Philadelphia Quakers sisters bought the early 19th century barn and converted it into their own eccentric summer home and art salon in the early 1930s. They designed the house and the garden, and filled it with furnishings—most selected on the basis of signs from god—that were as quirky and as eccentric as themselves. Each room is graced by some of the sisters’ own, not particularly noteworthy paintings.
• Old Mill. The second oldest surviving building on the island and the oldest continually operating windmill in the country was built in 1746. It is still used today to demonstrate the grinding of corn.
• Old Gaol. The solid, two-story, metal-reinforced wood structure was built in 1805 as a replacement for an aging 17^th-century jail . Unlike many other jails of that time, the jail contained only four cells. The two ground-floor cells were for a very lax form of solitary. While the town did have more than its share of seedy whaling ship crewmembers, most of the crimes committed by both by residents and crewmembers were relatively minor–drunkenness, petty theft, and fighting often by drunks. Most who committed serious crimes, including murder, fled on ships before being apprehended. Those who were caught, were typically sent to the mainland for trial and punishment. The vast majority of Nantucket prisoners served sentences ranging from overnight to a few days, or perhaps weeks. Guards were lenient. They typically left cell doors open and prisoners were free to wander the yard (although they were often required to stay in the fence.) Some were allowed to go out for the day, as long as they returned at night. In fact, over the 127-year life of the prison, the most “hardened” criminal was William Chandler, a banker who was convicted of embezzlement and sentenced to five years (and pardoned after only a couple years). Chandler didn’t exactly do “hard time”. He was allowed to furnish his cell with his own furniture, accessories, and linen. He had access to whatever books he wanted and could go out into the yard as we wished. His wife was free to visit, bring home cooked meals, and even stay with him. After all, although he was in jail, this was Nantucket.
• Oldest House. The small, 1686, English settlement-style cottage was built as a wedding present for Jethro Coffin and Mary Gardner.

Exploring the Island via Harbor Cruise

We had lunch reservations at Toppers restaurant, at the Wauwinet resort on the far side of the island (see Restaurants below). We took the scenic water route to the restaurant courtesy of the resort’s hour-long water taxi which runs, for lunch and dinner, between Nantucket Town’s White Elephant Resort at the mouth of the harbor, all the way to the head at the Wauwinet.

The Harbor is surrounded by the main island to the south and the Coatue nature reserve on the north. The vegetation-covered spit of sand is managed by the Land Trust and accessible by 4WD vehicle (by permit) or by guided tour. The southern shore of the harbor is lined by large homes and huge mansions along its entire length. Many of the most impressive of these are visible only by water. Although they are impressive from one end of the harbor to the other, the further up-harbor (east) you go, the more impressive they generally become. Two of the most exclusive sections of the island are when reaching the narrow channel at Pocomo and the end of the harbor at Wauwinet. This is where you see former Gamble mansion (of Proctor & Gamble fame).

The further reaches of Wauwinet is home to a number of huge, multi-acre estates with older, more traditional summer homes and compounds that belong to such notable families as the Mellons, the Roosevelts and the DuPonts. Beyond them, as the furthest end of the harbor, where Wauwinet meets Coatue, is a strip of land so narrow that a house built atop it is very close to, and can see both, the harbor and the Atlantic. Although this area has some of the island’s grandest old homes, it is sufficiently remote that it is not even served by electric lines. These homes, therefore, must rely on their own generators.

Just inside the head of the bay are a set of oyster beds that serve local restaurants.

Other Sections of Nantucket

While we walked Nantucket Town and saw the harbor shoreline by boat, we briefly explored a number of other sections of the island by car and through selective stops to particularly interesting sites.

Madaket

This is one of the island’s few “Middle-Class” communities that is nice, but not quite as expensive as many of the others. Renowned for its beaches and its sunsets, it was once a sleepy town with a handful of detached homes, especially along the harbor and the beach (so-called Old Madaket) and the island’s only townhouses (of which no more can be built).

The area has exploded with mini-mansions with their own swimming pools and cabanas. In an effort to keep Madaket affordable (or what passes for affordable on the island), the council passed ordinances that impose height restrictions and that require a complex and restrictive permitting process for such amenities. All in an effort to retain the area’s own character.

Old Madaket is also one of the places where you can see the phenomenon that is affecting the island’s entire shoreline and that will ultimately overtake the entire island: erosion. During every storm, more and more of the island’s sandy shoreline is washed into the sea. Beachfront land disappears and homes built near the shore end up closer and closer to the sea. If they have enough room between their home and the road, homeowners can pay to have their home moved further inland to protect them from being washed into the sea (an expensive process for which insurance does not pay). Or, they can leave the homes where they are, wait for them to disappear, collect whatever insurance they had been able to afford, and lose not only their home, but their property. (Homeowners who select the latter course can never again get insurance on what is left of that property. The third option is that they can buy another piece of land on which another building is already likely to exist, tear down the existing home and move their own home onto that site.

Siasconset

“Sconset” is lovely, very expensive section on the northeastern tip of the island. It has a tiny commercial center (essentially a general store and a post office) and a mix of shingled homes that range from tiny cottages to large mansions and compounds, most of which have colorful gardens and are surrounded by tall, manicured hedges that protect residents from gawking tourists (like us). A public walking path runs at the edge of a bluff. On one side of the bluff are wildflower-strewn fields and pretty sandy patches that lead to the ocean. On the other are the backs of the otherwise hidden houses, with their lawns, gardens and sweeping views out to the sea.

Nantucket Cliffs and Cliff Beach

Overlooking the beach and the ocean are among the most desirable and expensive locations on the island. The Cliffs is home to some of the largest, most expensive homes on the island. The beach is home to Galley Beach, one of the island’s premier beach clubs and restaurants.

Eel Point

Like the Cliffs, this elevated North Shore ocean-facing bluff is home to several large homes.

Cisco

While the small beach area on the South Shore is certainly an attraction, Cisco’s highlights are two businesses that have taken the island by storm. T

• Cisco Brewers brewery/winery and distillery makes a number of the island’s craft alcoholic beverages (including a wide range of distilled spirits, beers, wines made from Yakima Valley Washington fruit), hard ciders, and sangrias. As important as the beverages is the entertainment venue they created around them. The “campus” has a separate building at which you can taste and buy the different types of beverage, a raw bar, food trucks (tacos, lobster rolls, etc.), tables, bands, a store from which you can buy Cisco-labeled clothes and accessories, and a playground to occupy children while their parents are otherwise engaged.
• Bartlett Farm is a large island-based farm that grows a range of vegetables, including its rightly famous Bartlett beefsteak tomatoes. Almost as important as the produce is the retail store which sells not only its produce, but also plants, fresh seafood, high-end cold cuts, artisanal foods and coffees, ready-to-eat foods, a few staples and, like Cisco, a children’s playground.

Nantucket Restaurants

Ship’s Inn

Our dinner at this wonderful restaurant had a surprisingly comprehensive, moderately-priced wine list that encompassed representative wines from wine regions from around the world. Three of us started our dinner with grilled sea scallops with black ruffle hollandaise; sautéed halibut with wild mushroom risotto, pea puree and morel sauce; and grilled swordfish with truffle baked potato and lemon thyme beurre blanc. Our dessert was a no-brainer once we saw a type of soufflé that we had never before heard of—coconut with crème anglaise. It was was well worth the calories. Our wine was a Chanson Vire-Clesse (a recently designated Chablis appellation) and a Bonny Dune “Vin de Glaciere” Late Harvest Riesling that accompanied our dessert.

The Charlie Noble Restaurant

We had a lunch of fried belly clams and stuffed quahogs with chorizo and brioche (salty and not very interesting) and an enjoyable fried cod sandwich.

Galley Beach

We had three wonderful dinner dishes at one of the island’s premier (not to speak of most expensive) restaurants. Pernod-scented escargot with tomato garlic butter and pimento pastry, a two-pound truffle-butter poached lobster with English peas, Hon-shimeji mushrooms and potato medallions, and grilled veal chop with wild rice salad and wild mushroom brandy sauce. A perfect meal with a perfect wine, a Bachlet-Monnot Maranges 1er cru Fussiere red Burgundy. All this with very good service, in a lovely setting, with a beautiful sunset. What more could we want, other than perhaps, lower prices?

Topper’s at the Wauwinet Resort

The restaurant has a lovely patio and garden that overlooks the harbor. It is a charming place for a relaxing meal. We had three huge and very good lunch dishes: lobster roll on brioche with brown butter mayo, bibb lettuce, and a side of double-fried Old Bay French fries; organic, buttermilk fried chicken breast sandwich with avocado, cilantro and kimchee and more Old Bay fries; and free range veal Wienerschnitzel with cucumber salad, potato salad, and loganberry jam. We shared a bottle of Felsner Lessterrassen Gruner Veltliner. A wonderful meal and a beautiful, tranquil setting. And, as mentioned above, the hour long boat ride got one in the mood for a beautiful, relaxing lunch.

And this is not to forget Nantucket’s native foods. There is, of course, the Bartlett Farm produce, especially the wonderful beefsteak tomatoes that we enjoyed with mozzarella, basil, and balsamic vinegar. Then there are the gifts from the sea: the wonderfully sweet and rich Nantucket Bay scallops and nice local oysters.

Other Intriguing Things About Nantucket

Before we leave Nantucket, we wanted to mention a couple of additional interesting tidbits.

• The financing of whaling ship voyages became the whaling-era equivalent of playing the stock market. While wealthy industrialists and merchants provided the primary financing for whale ship voyages, less wealthy residents also got into the action by buying small shares of the potential profits of multiple planned voyages (in an early form of portfolio diversification) in the hopes that at least one of their ships would hit a jackpot.
• Although most Quakers supported abolition, a few actually owned slaves. Most others, while working for abolition, and in some cases, even hiding runaway slaves, would not publicly associate with even free African Americans.
• Prince Boston was a free, highly-skilled slave who worked on whaling ships and who, partly with the help of William Rotch, not only gained his freedom, but also became the first African-American whaling ship captain and also an owner of his own ships. Since blacks were not allowed into public schools, he hired private tutors to educate his daughter and eventually (although too late for his daughter) won a court case to secure black admission into Massachusetts public schools.

William Rotch

One of the islands leading merchants merits particular mention. William Rotch  was a prominent ship owner and merchant who profited mightily from the whale oil trade. He, for example, initially allied with John Hancock in selling of whale oil and candles to England. But when Hancock began to buy and directly sell whale oil, Rotch undercut his pricing and forced Hancock to take a steep loss. Hancock retaliated by prompting his Boston compatriots to target Rotch’s ships in their Boston Tea Party raid.

Rotch, however, was not satisfied with earning shipping profits on whale oil, tea, and other commodities. He recognized the profit potential of adding value to the oil by making and selling Spermaceti candles. Unfortunately, neither he nor other Nantucket merchants knew how to most effectively produce these candles. He, therefore, hired an industrial spy to learn the secrets of the candle making industry from a Connecticut company. Using this intelligence, he created Nantucket’s first Spermaceti candle company, which greatly increased the profits he and all of Nantucket derived from whale oil.

In addition to being a shrewd businessman, Rotch had a desire to help oppressed African Americans. A whaling captain that he hired to lead a voyage brought a skilled slave, Prince Boston (see above) onto his crew. When the captain refused to pay Boston what he was due from the successful voyage, Rotch demanded that the captain pay Boston. The captain refused and Rotch threatened to hire John Adams to sue the captain. Not only did the captain end up paying the slave, he also ended up freeing him. Boston went on to become not only the first black whaling ship captain, but also a ship owner!