Just beyond daybreak on an oddly mild November morn in 2006, the ferry terminal in Vineyard Haven was abuzz with sleepy teenagers and an odd lot of their elders, clad nearly to a person in something purple. They swarmed into the belly of the ferry Martha’s Vineyard with a caravan of buses, gear-filled minivans, and a state police cruiser. All were bound for Nantucket for the premier event on the bi-Island calendar: the annual high school gridiron contest for the coveted Island Cup. Later that afternoon, the Vineyarders would try to defend their three-year grip on the cup from their archrivals, the Nantucket Whalers.

As the ferry slipped past Cape Pogue light, Cindy West of Vineyard Haven sipped coffee and squinted toward the horizon from the starboard deck. She’s lived on the Vineyard for twenty-five years. “I’ve never been to Nantucket before,” said the Martha’s Vineyard Public Charter School teacher. “I don’t know why....”

Cindy was in good company. Many of her fellow passengers had never been to Nantucket – except maybe to play school sports or to root for the teams. Their impressions of their so-called sister island were sparse.

“I heard it’s really flat,” offered one teenage girl.

True.

“I suppose people over there are a lot like we are,” said a parent.

True – more or less. One of the most striking traits shared by many Vineyarders and Nantucketers is a resounding lack of interest in each other’s island.

Like Cindy, many “Vintucketers” (work with me, readers) are hard pressed to explain the apathy. Emily Hall, a Nantucket native, may be on to something when she says the attitude emanates from the rivalries in school sports: “If you grow up here, you can’t help but dislike Martha’s Vineyard,” says the twenty-one-year-old clothing store sales associate. “It’s ingrained.”

Yet most Vintucketers, be they natives or wash-ashores, claim it’s nothing personal. When they get a chance to go off-Island, they go to a Red Sox game. Or a shopping mall. Or maybe the Florida Keys, in winter. The point is: People who live on isolated bits of ice age rubble do not yearn to discover the isolated bit of ice age rubble next door.

Ally Reed of West Tisbury once took her lackadaisical preteenage sons to Nantucket “on principle,” she says. “Their only visible enthusiasm was for the big cobblestones on Main Street. Otherwise, it was just more sand and lighthouses to them.”

Sooner or later, whether on principle or for sport, Vineyarders might consider putting down their “Harpoon the Whalers” signs long enough to get to know that island and those islanders at the other end of the Sound. Nowadays, unfortunately, there are real excuses not to do so in person. Aside from the biennial crossings for the Island Cup match, the long era of Nantucket day trips by ferry came to an end in 2005. Yet even from a distance, Vineyarders might contemplate a few random questions. No one will be outed for doing so. Purple sweatshirts won’t turn lavender. And hugging of Nantucketers is not required.

Where did this “sister island” thing come from?

The concept is not without provenance: Both Nantucket and Martha’s Vineyard were originally inhabited by Wampanoag. Captain Bartholomew Gosnold of England landed on both Islands in 1602. Both Islands were deeded to Thomas Mayhew in 1641. And since Nantucket’s poor soil wasn’t fit for raising crops, Mayhew used Nantucket – and its natives – to raise sheep for the English settlements on the Vineyard.

On Nantucket, English settlement didn’t begin in earnest until around 1659. In lieu of farming, the settlers did what the Wampanoag did: hunt whales. Nantucket’s boom years of whaling began in the mid-1700s, nearly a century before the height of a relatively small boom on the Vineyard, where agriculture sufficiently sustained the economy. Yet some Nantucket whaling ships were steered by captains who lived in Edgartown.

By 1870, when whale oil took a back seat to the kerosene market, both Islands turned to summer tourism to keep their economies alive. Until the mid-1900s, a strong agricultural sector helped the Vineyard maintain its economic and social diversity. The Nantucket economy, on the other hand, has been pegged almost entirely to the resort business for more than a century.

Why does Nantucket seem more remote than the Vineyard?

Because it is. Lying about thirty miles off Cape Cod, it’s nearly ten times farther away from America. In native language, Nantucket literally means “far away island.” Nantucketers thus describe themselves with prideful terms like independent, hardy, and self-reliant. Some even give in to mild condescension:

In a recent issue of the weekly circular Yesterday’s Island, writer Robert P. Barsanti scoffed that, on a clear day, people in East Falmouth can see cars moving in Oak Bluffs. “You can’t see Nantucket from the mainland. Unlike the Vineyard, it doesn’t hang right offshore so close that a sunfish or a particularly energetic swimmer could dream of paddling over for lunch before heading back with the tide.”

Nantucketers don’t dash off to mainland jobs, doctors, Wal-Marts, or nail salons to the extent that Vineyarders do. Perhaps that too is a function of remoteness. Ferrying a car to Hyannis and back is a $360 setback much of the year. Importing goods and services is slow, costly, or both.

“Whatever impacts us on the Vineyard impacts them ten times more,” says Vineyarder Juanita Suarez Espino of Oak Bluffs. There’s at least one anomaly: Their gasoline prices are lower. Go figure.

Just how small is that island?

Shaped somewhat like a swinging hammock, Nantucket stretches 14 miles east to west, and 3.5 miles north to south. It comprises roughly 50 square miles, or half the land area of the Vineyard.

In people terms, Nantucket has a year-round population of some 10,000 residents, compared with the Vineyard’s some 15,000. In summer, Nantucket’s population swells to 55,000. The seasonal Vineyard population is about 75,000.

Yet the size of an island isn’t a mere matter of numbers. It’s also a state of mind.

On Island Cup day, the five-float Island Cup parade motored through downtown Nantucket in a blur of blue and white. Fans emerged from storefronts and homes to cheer from the narrow sidewalks. The parade passed in five minutes, tops. That afternoon, during half time at the varsity football match, the Whalers booster club presented a prize of $150 to the high school freshmen for Best Float.

“It’s like old-time, small-town America,” said Nantucketer Linda Sonnonstine, who marveled at the festivities from the sidelines, along with her husband Craig Sperry. Two weeks earlier, the longtime seasonal residents had moved from California and set down year-round roots here.

Many Nantucketers feel the smallness of their island makes it a nurturing, cohesive nest. The term “close-knit” comes up just shy of ad nauseam. Judith Wodynsky, director of external relations for the Nantucket Historical Association, has lived on both Islands. She likes Nantucket better. “It’s smaller and less cliquish. You get to know people better here.”

Annie Sager is entertainment editor of the Nantucket High School newspaper Veritas. In a recent Vineyard-bashing humor essay, she wrote: “Who wants to go to a school where you don’t know every person in your school?” The Class of ’07 numbered 97 students, compared with 197 for the Vineyard.

“You are on stage as soon as you walk out of your house,” wrote Robert Barsanti, in his humorous tribute to his homeland. “You can’t get blotto at the [Chicken] Box and expect to become invisible.”

But hey: Delete “Box” and insert “Lampost,” and he’s talking Martha’s Vineyard.

Still, there’s a paramount societal distinction between the two small Islands: Nantucket is one close-knit town with a central heartbeat. The Vineyard comprises six close-knit towns, each with its own pulse. Vineyard visitors, including some Nantucketers, are charmed by the contrasts between bucolic Chilmark and whimsical Oak Bluffs, for example. But Chilmarkers are generally more interested in Chilmark affairs than in Oak Bluffs affairs. Try to get the Vineyard’s towns together on an Island-wide initiative – the high school budget, affordable housing, whatever – and you may have trouble.

What’s the place look like?

Nantucket is indeed mostly flat. Due to the whims of ancient glaciers, Nantucket is short on the topographical diversity that characterizes the Vineyard. Experts predict that global warming and rising seas may cause the island to disappear in seven hundred years or so. Already, in the eastern village of Siasconset, northeasters are eroding the low bluffs at a rate of ten feet a year.

The island has its own brand of natural beauty. In lieu of the dense woodlands, rolling hills, and clay cliffs that characterize the Vineyard, it embraces one-third of America’s grassy heathlands, and used to have the world’s largest cranberry bog (before it was broken down into more water-efficient units).
And by the way: Nantucket’s eighty-two miles of spectacular beaches are 100 percent open to the public, thanks largely to the benevolence of nonprofit conservation organizations and private landowners. Some of the best beaches on the Vineyard are not.

About 46 percent of Nantucket is protected from development, compared with about 40 percent of Martha’s Vineyard. As on the Vineyard, Nantucket’s protections are afforded by a mix of public and private initiatives. The Nantucket Islands Land Bank, created in 1983, was the nation’s first institution
dedicated to buying and maintaining conservation areas by means of assessments on local real estate transactions. It served as the model for other such organizations, including the Martha’s Vineyard Land Bank, circa 1986.

Whereas Vintucketers may be more or less evenly passionate about protecting the natural environment, Nantucket is far more strident than the Vineyard when it comes to preserving the built environment, or “town character.” Martha’s Vineyard has four historic districts of limited size. Nantucket has one such district – the entire island – and a thick set of building guidelines and restrictions to go with it. In the downtown area – an early nineteenth-century gem with a classy Edgartown feel – architectural styles are regulated right down to the pitch of the roofs. Sashes, railings, and door frames are limited in hue to white or light gray. However, the doors themselves may go nuts in barn red, Brewster green, or any of six additional approved colors.

“Some people argue, ‘That’s so authoritative; this is supposed to be America,’” says Tracy Bakalar, executive director of the Nantucket Island Chamber
of Commerce. Buildings beyond the town center have more leeway. “Trophy houses are possible if you can’t see them from the road.”

One Nantucket real estate agent claims that many of today’s buyers ask one thing only: “Am I allowed to tear it down?”

Nantucket, like the Vineyard, eschews chain stores and has managed to maintain town character with its streetscape of independent retailers. But after Ralph Lauren bought and moved into one of the most prominent storefronts on Main Street two years ago, Nantucket quickly sought and won permission from Massachusetts to ban chain stores in the future. Ralph Lauren was grandfathered. Previously, chain stores that had come to Nantucket lasted only a couple of years before the owners closed shop.

What about the “rich and famous”?

Nantucket endures the same high-brow stereotypes the Vineyard does, with perhaps more of a slant toward bow ties and yachts.

“The impression here is that the Vineyard has more celebrities and that we have more rich people,” says Barry Mailloux, as he serves up a bowl of chowder at the counter of the Atlantic Café. The “AC” is one of Nantucket’s last affordable eateries.

Nantucket’s luminaries probably get more press in Fortune than in Entertainment Weekly. They include the likes of Jack Welch, Peter Lynch, and Theresa Heinz Kerry (of General Electric, Fidelity Investments, and Heinz Foods fame, respectively).

Sue Ray of the University of Nantucket, a souvenir clothing store, sizes things up this way: “There are more billionaires on this island than anywhere on this earth, and that’s the God’s honest truth,” she says with a hearty laugh. “But that’s what keeps us all in business.”

Real estate agent Dave Beaumont generously spouts rumors: “Someone told me the U.S. has two hundred billionaires, and seventy of them have property on Nantucket,” he volunteers. “I heard that Greenwich, Connecticut, practically owns the island now….”

Non-resident property owners account for a commanding 89 percent of the tax base on Nantucket, where property valuations exceed $20 billion. They also dig deep to support Nantucket Cottage Hospital and other island charities.

On a ferry trip from the Vineyard to Nantucket a few years ago, an unassuming Peter Lynch offered to take a photo of the former Californians Linda and Craig. “It was an example of how relaxed people are when they’re on the Islands,” says Craig. “People are comfortable with each other, no matter who they are.”

Matthew Stackpole, director of the Martha’s Vineyard Museum and a Vintucketer of four centuries’ lineage, has lived on both Islands: “The cool thing about both Islands,” says the West Tisbury resident, “is that you get to rub shoulders with interesting people who are different from you.”

Indeed, the notion that everybody is rich and/or famous is a flagrant Vintucket misconception. Yet shopkeeper Sue, for one, feels that conspicuous wealth increasingly dominates Nantucket’s character. “It didn’t used to be that way,” laments the longtime resident.

As on the Vineyard, some year-round Nantucketers have trickled away from the island in recent years. “Some are leaving because they can’t afford to live here anymore, and some are leaving just to cash out,” says Tracy from the Chamber. “For what they can make on the sale of their property, they can buy two lots in Maine.” To make up for the dwindling supply of homegrown service workers, Nantucket, like the Vineyard, depends on foreign seasonal workers from Bulgaria, Jamaica, and elsewhere.

Vineyard caretaker Clare Low, of Oak Bluffs, quips, “Soon the millionaires on Nantucket will be mowing lawns for the billionaires.”

Does Nantucket have washashores?

Some call non-natives “washashores,” just as Vineyarders do. Others call them “’round the Pointers,” in reference to Brant Point at the entrance to Nantucket harbor. Still others call them “coots.”

“It’s a historic term,” Tracy says. “Nobody knows its origin.”

What’s the hot-button issue over there?

Vintucketers are largely concerned about the same things, e.g., affordable housing, traffic, growth, open lands, and sustainability. On the latter issue, Tracy of the Chamber of Commerce echoes a sentiment common to both Islands: “It costs more to live in a great place,” she says, “and I’m willing to pay the premium.”

Affordable housing is the toughest nut – even tougher on Nantucket than on the Vineyard. Although the median household income for year-rounders is somewhat higher for Nantucketers, they have a slightly lower rate of homeownership. The dominance of the silk glove market is just one factor. Scarcity of real estate supply is another: Nantucket is about thirty thousand acres, and nearly half of it is off-limits to development. To make things work, some homeowners do the “Nantucket shuffle,” moving out for the summer so that vacation renters can move in. Sounds familiar.

Through August of 2007, Nantucket homes sold at a median $2.3 million for the year. Just 6 or 7 percent of property sales were below a million dollars, and they were largely fixer-uppers, condos, and vacant land. Over the past year, as the U.S. housing market has plummeted and the Vineyard market has slumped, Nantucket prices have barely registered a down-tick. Skewing the picture just a tad is an August sale of 9.5 acres of land for $26.5 million – the single largest residential transaction in Nantucket history.

According to a June housing report, “the typical Nantucket homeowner uses less leverage in a more sophisticated manner than the national average.”

Translation: People who can buy property on Nantucket are immune from the economic cycles that bite everybody else in the butt.

“They don’t even know how to spell recession,” says Oak Bluffs real estate agent Alan Schweikert.

Some creative housing initiatives for low- and middle-income residents are underway, including an embattled proposal to establish an affordable housing bank à la the land bank. The Vineyard has a similar measure on the table.

Meantime, the morning rush hour brings in planeloads of workers with lunch pails to Nantucket’s airport, the second busiest in Massachusetts. Employers like NStar, UPS, and major plumbing contractors foot the air fare or at least subsidize it. “I personally hate to see companies in Hyannis coming in and taking our money,” says Tracy, “but it’s a necessary evil.”

What’s there for visitors to do on Nantucket?

Plenty, although visitors to both Islands generally conclude the Vineyard offers a greater diversity of things to do and see.

Thirty years ago, Nantucket in summertime was relatively quiet compared to the touristy-ness of Martha’s Vineyard. But that was then. Today, day trippers and short-term vacationers abound, especially since the advent of fast-ferry travel from Hyannis.

In late April, the spring shoulder season officially opens with “Daffy Weekend,” a festival that’s rather like a Tournament of Roses in yellow. The fall season ends with the Christmas Stroll in December, which is akin to Christmas in Edgartown weekend. Just add wandering carolers and a few Martha’s Vineyard Chamber of Commerce staffers on a shopping spree...hmmm.

Nantucket is predictably big on water sports – swimming, boating, fishing, kayaking – and unlike the Vineyard, it’s far enough into the Atlantic to offer whale-watching cruises. People can also take seal-watching cruises to nearby Muskeget Island.

Biking is popular, and because the island is smaller and flatter than the Vineyard, the average cyclist can pedal the island end to end over the course of a day or two. One can truly do without a car, which is just as well, because in-town parking in summer is as aggravating as on the Vineyard. (Nantucket does heavily promote its public buses as a solution.)

The Whaling Museum is a star attraction worthy of utmost Vineyard envy. And at the Loines Observatory, stargazers on the Far Away Island can view far away planets.

Shopping time: Antiques shops outnumber those on the Vineyard, and they tend to evoke Louis XIV rather than Ma and Pa Kettle. Jewelry shops seem to sparkle with more diamonds and glittery things than Vineyard shops do. Predictably, the Golden Basket sells plenty of iconic Nantucket basket charms, but the homespun-looking wampum that sells well in the Edgartown outlet doesn’t make it there. And for T-shirts and sweats, there’s the Yellow Dog…hmmm.

On a day trip of Nantucket biking and shopping, Judy Holland of Vineyard Haven was surprised to hear salespeople in two different Main Street stores say: “We’re not like shops on the Vineyard.” Her takeaway: “They meant they’re more high-end.”

“Nantucket seems to be pricing out some tourists,” says Harvey Young, proprietor of Young’s Bicycle Shop, a business launched by his grandfather seventy-six years ago. “The thinking used to be that we should sell a whole bunch of hot dogs and get as many people here as possible. Then people got the idea to just sell a couple of steaks and relax. Less work; more income. Now it’s all about steaks,” he says with a shrug.

Want to stay for a while? Summer rentals go for as much as $75,000 per week, and according to agent Dave Beaumont, one weekly rental went for a hundred grand last summer. At the other end of the spectrum, a few homes rent for $1,500 to $2,000 a week to unfussy customers who might just want to fish and crash.

“I feel sorry for people,” says shopkeeper Sue Ray. “A couple of young newlyweds recently came in the store and asked me where they could eat without spending a fortune. There used to be two nice places – one in town and one at the airport. Both are gone.” She pointed the couple in the direction of the AC, across the street.

When you check in for a flight from Nantucket to Martha’s Vineyard using a photo I.D. with a Vineyard address, what does the Cape Air agent say?

“Oh! You actually live over there!”

What’s that supposed to mean?

“I didn’t mean to be rude,” said Linda Rosenberg with an embarrassed laugh. “It’s just that you’re the first Vineyarder I’ve seen since I started this job two months ago. Most people traveling to the Vineyard are tourists who are bouncing around between the Cape and the Islands.”

Does she ever go to the Vineyard herself?

“No, not since my kids were in sports.”

Which Island has the better high school football team?

In the dark of night, the Vineyard Haven terminal was alive with fire engine lights, police sirens, flashing cameras, and noisy celebrants as the Martha’s Vineyard pulled into the slip. In a homecoming worthy of astronauts, the Martha’s Vineyard Vineyarders marched off the car deck hoisting the Island Cup high in the air. It was their fourth consecutive triumph. ’Nough said.