The locals are a tight-lipped breed when it comes to divulging their favorite spots. But we'll let you in on their secrets, in this essential guide to the Faraway Island. Just don't tell them who sent you.

Max Kim-Bee

In the past decade, Nantucket residents, both year-round and migratory, began to grow restless. "There are too many new houses here," they muttered to one another. Too many cell phones, too much traffic, too many people. As the year 2000 approached, islanders tightened building limits, made planes fly offshore on approach, and circulated bumper stickers that read twenty is plenty (as in miles per hour). These were worrisome years on the Faraway Island, as some have translated Nantucket's ancient Indian name.

Through it all, the blue Atlantic sent perfect waves onto white sands. On Main Street, farmers sold produce off the backs of trucks. Climbing roses bloomed by the thousands up cottage walls in Siasconset, that most English of New England villages. Sandcastles were created on Children's and Jetties Beaches. Bluefish blitzed at Great Point and striped bass ghosted along the flats off Eel Point. Ice clinked in glasses. Slabs of fish crackled on grills. And in the spring of the new millennium, the essentials of paradise endured.

the lay of the land

"Take out your map and look at it." So Melville wrote of Nantucket in Moby Dick, perhaps as a tacit admission that he had never been to his protagonist's island. Officially it's all one town, but in reality there are several distinct neighborhoods. Where you choose to stay will affect your overall experience.

Nantucket town: Nantucket has more than 800 pre-Civil War houses in its historic district. Most were built around the harbor in "town" (as everyone calls it) during the island's reign as capital of the whaling business. Wandering the streets lined with 1700's and 1800's captains' houses is an architectural education in itself. West of Steamboat Wharf begins the land of generously porched summer retreats built in the post-whaling period.

Siasconset: At the island's extreme eastern end, the heart of this miniature fishing village—"Sconset"—is almost unchanged from the early 1700's, when Nantucket town residents began summering here. On either side along the bluffs are later-vintage summer places.

Madaket: Across the island from Sconset, both geographically and temperamentally, lies Madaket. Nothing is ever scruffy on Nantucket, but Madaket is laid-back enough for some people to sniff at. If you didn't clip your hedge for a season, none of your neighbors would notice.

Quidnet, Quaise, and all the rest: Each of Nantucket's smaller neighborhoods has its own flavor. For your purposes: North of Polpis Road, where Quidnet and Quaise are located, think old family compounds on winding roads. South of Milestone Road, think subdivisions by the sea.

top bike routes

The sublime six-mile Hummock Pond loop starts just east of where Cliffs Road intersects with Madaket Road. • For the best sense of the inland island, mountain bike the occasionally steep, three-mile-long Barnard Valley Road, from its start at the intersection of Hoicks Hollow and Polpis Roads. Take drinking water and a decent map and make your way across the moors to Altar Rock. • Of the many paved bike paths, the Polpis Road route is one of the best. It winds alongside marshes and beside ponds and cranberry bogs, and passes the Lifesaving Museum.

walk this way

Left over from the days of looking for whale spouts from shore, the Sconset Bluff Walk is a studiously unadvertised public way that takes you right through the front yards of the island's choicest shingle-style masterpieces, rivaled only by those on Hulbert Avenue and Cliff Road in town. It begins deceptively enough: at the end of Front Street in Sconset is a sign that says FOOTPATH ONLY, NO BIKES, which appears to refer to a very steep and narrow trail heading down to the right to Codfish Park. The path you want is the less obvious one to the left, through the privet hedges and on along the lip of the land. Residents are accustomed to the parade of strangers, but if you do the bluff walk at cocktail hour, don't expect to be invited up onto the porch for a drink.

best fishing

All Points Bulletin: A bluefish or a striper has at some time been hauled out of the surf along every yard of Nantucket's south and east shores. But to be alone, try below the old military reservation at Tom Nevers. When in doubt about where to go, join the all-terrain armada at the points: Smith's and Great to heave big plugs into the surf, Eel to wade for bass with a fly rod.

where to stay

On Nantucket, rooms are often small and prices high, which is only partially due to supply and demand. With a few notable exceptions, most of the lodging is in guesthouses built before 1900. Unless noted, the following hotels are in Nantucket town, and prices listed are for high season, which begins in July.

the inn thing

Built in 1709, the nine-room Woodbox Inn (29 Fair St.; 508/228-0587; doubles from $155) makes Nantucket's 19th-century houses look dreadfully nouveau. Nobody has wider floorboards or smaller windowpanes—and nobody, but nobody, has better popovers. An old silk factory is now the Sherburne Inn (10 Gay St.; 888/577-4425 or 508/228-4425; doubles from $150), with eight larger-than-average rooms. Some of the 12 rooms at the Nesbitt Inn (21 Broad St.; 508/228-0156; doubles from $65) are frayed—in a Victorian way—but the location near the ferry terminal couldn't be better. Among the best of Nantucket's many guesthouses are a pair owned by the Carl family. Mom and Pop oversee the five-room Chestnut House (3 Chestnut St.; 508/228-0049; doubles from $150). Next door, their children run the 10-room Hawthorn House (2 Chestnut St.; 508/228-1468; doubles from $145).

insider's secret

After a few seasons at Wade Cottages (35 Shell St., Siasconset; 508/257-6308; doubles from $240, three-night minimum), you'll feel as if you're returning to your family compound. The effect might be due to the stairway down to the beach; the well-used beach chairs; the relaxed owners; or the charming accommodations in eight rooms, six apartments, and three cottages.

the classics

The Wauwinet (120 Wauwinet Rd., Wauwinet; 800/426-8718 or 508/228-0145; doubles from $380) is unmatched. One of the first resorts built on the island, it now has twice as many staff members as guests—not to mention bikes, kayaks, croquet and tennis courts, and sailboats. The service is impeccable, though some of the 35 rooms are so cozy that you feel you'd better pass up room service for lack of space to put the tray. On a bluff in Sconset there's the most romantic getaway: Summer House Cottages (Ocean Ave., Siasconset; 508/257-4577; doubles from $550). The 10 rooms are really self-contained little rose-covered cottages, all arranged around a garden.

where to eat
top tastings

Don't have a reservation?Check for seats at the upstairs bar of 21 Federal (21 Federal St.; 508/228-2121; dinner for two $100). The menu changes weekly and manages to be creative without adding that telltale sixth fruity ingredient that announces "Innovative chef at work." At the Boarding House (12 Federal St.; 508/228-9622; dinner for two $100), where reservations are required, Atlantic seafood gets the Pacific Rim treatment. On summer nights, the outdoor tables are hard to come by and hard to beat—there's a cheap bistro menu. The dining room of Topper's (508/228-8768; dinner for two $150), at the Wauwinet hotel, is elegant in a restrained, gentlemen-will-be-more-comfortable-in-blue-blazers way. By all means, don't drive: take the complimentary boat ride to and from town.

something old, something new

Nantucketers love the Club Car (1 Main St.; 508/228-1101; dinner for two $125), a slightly stodgy standard. Don't be put off by the claustrophobic entrance through the last remnant of the old Nantucket railroad; once inside you'll find they do good things to sweetbreads. The couple who owns the Boarding House recently opened Pearl (12 Federal St.; 508/228-9701; dinner for two $150), which has a tropical-aquarium theme and requires reservations. The tuna martini is the best appetizer on the island.

let's get romantic

A few blocks from the busy center of town but still in the historic heart, American Seasons (80 Centre St.; 508/228-7111; dinner for two $90) exudes warmth, particularly in the chilly shoulder seasons. Find out whether or not you and your date are compatible at the Company of the Cauldron (5 India St.; 508/228-4016; dinner for two $100): the lights are low, the tables snug, the mood intimate—and, since there's only one entrée each evening, you both eat the same thing.


For French in the classic style, there's the Chanticleer (9 New St., Siasconset; 508/257-6231; dinner for two $150). The main dining room feels more like a country-club banquet hall in suburban Maryland, but regulars know to ask for seats in the handsome bar, where the presence of smokers makes it all the more French.

top of the morning

Whether you sit at the counter or at one of the slightly cramped tables, the ambiance of Black-Eyed Susan's (10 India St.; 508/325-0308; breakfast for two $20) is casual. Breakfast is the specialty, though the coffee is a tad pedestrian. If you must have a jolt, get it at Espresso Café (40 Main St.; 508/325-0308).

side by side

There are two classic old drugstore soda fountains in town, located in two classic old drugstores right next door to each other: Nantucket Pharmacy and David's Soda Fountain at Congdon's Pharmacy. For generations, Nantucketers haven't been able to make up their minds about which is better, so you don't have to either. But if you want a smoked Baltic sprat sandwich on rye, go to David's (47 Main St.; 508/228-4549; lunch for two $10).

where to shop

With a few exceptions, the best shops lie in the historic heart of town, along Main, Federal, and Centre Streets.

it's in the bag

Originally produced during long hours at sea on floating lighthouses, the Nantucket lightship basket is now an institution. The intricately woven lidded baskets can be found at practically every shop along Main Street, but the finest are sold by a few venerable craftspeople. The best sources are the Ottisons (170 Orange St.; 508/228-9345) and Nap Plank, who runs Nantucket Basket Works (14 Daves St.; 508/228-2518).

you've got the look

Since 1913 Murray's Toggery Shop (62 Main St.; 508/228-0437) has been home to the famous "Nantucket red" trousers, the Sperry Top-Sider, and everything else the locals have been wearing from the time they were in boarding school. Peter Beaton Hat Studio (16 1/2 Federal St.; 508/228-8684) is the source for those lovely straw hats with the upturned brim and wide ribbon you see all the women wearing. If the fog has rolled in and raised goose bumps, Cashmere Nantucket (32 Centre St.; 508/228-7611) is your savior.

need a house gift?

The best presents—Simon Pearce martini glasses, perhaps?—come from Bramhall & Dunn (16 Federal St.; 508/228-4688). For the truffles that spell trouble for anyone who says, "Hey, I'm on vacation, I'm going to eat what I want," there's Sweet Inspirations of Nantucket (26 Centre St.; 508/228-5814). Everyone stops at Nantucket Looms (16 Main St.; 508/228-1908) eventually, if not to buy handmade sweaters, then to read the sign with distances from Nantucket to various points around the world.

on the farm

Where to go if you've got a hankering for fresh produce and feel like venturing beyond the wagons parked on Main Street every morning?Some may tell you that the popular stand at Bartlett's Ocean View Farm (33 Bartlett Farm Rd.; 508/228-9403) is the only place to go. They aren't wrong: it's purely a matter of opinion. For a more intimate vegetable experience, try the stand at Moor's End Farm (40 Polpis Rd.; 508/228-2674).

in the end, it's all about the beach

There are plenty of reasons to visit Nantucket, but surrounding all of them is a sandy boundary between sea and land. Unlike some other parts of Massachusetts that shall go unnamed, virtually all the beaches on Nantucket are open and easily accessible to the public.

baywatch at your service

Heading west around the island from town, these are the principal lifeguarded beaches:

Children's Beach: As it sounds. No waves, little current (it's on the sheltered waters of Nantucket Harbor), plenty of hot dogs, playground equipment, rest rooms with diaper-changing stations, and T-shirt tie-dying programs on Fridays after noon.

Jetties Beach: The median age rises to somewhere around nine on Jetties, which is the best beach within walking distance of town.

Dionis Beach: Backed by dunes and out of town, this beach is prettier than either of the above, but it's still on the Sound.

Madaket Beach: The south shore beaches are for those who like big surf and a quick drop-off—in other words, the real ocean. Go at sunset.

Cisco Beach: More of the above, only without the view of the unfortunate waterfront architecture of Madaket.

Surfside Beach: Popular with families. On Fridays and Sundays the nearby airport can be busier than Boston's Logan.

Siasconset Beach: Beautiful, but scary when the surf's up.

where the locals go

Seasoned islanders have favorite spots that are far from the clustered towels near the lifeguard stations. They use names that often refer to nothing more official than a nearby landmark. The purists still get there on bikes, along not-well-marked roads, or in their trusty (and tastefully rusty) Jeep Wagoneers and Chevy Suburbans. But beware: Nantucket is one of those places where people buy a beach access sticker and try out the four-wheel drive on the sand. The resulting scene at Great Point, Smith's Point, and Eel Point is a cross between a tailgate party and a used-car lot.

Nobadeer and Madekecham Beaches: Both lie to the east of Surfside; the former is popular among the young, single, body-surfing set.

Quidnet Beach: Despite the trophy house looming over its barrier beach, the view from Quidnet over Sesachacha Pond toward Sankaty Head is awe-inspiring. No place to park; ride your bike.

Pocomo Beach: A somewhat stony beach for children and shell-seekers.

Coatue Beach: Rent a sea kayak; pack a lunch, plenty of water, and sunscreen; and plan to spend an entire day exploring the crescents and points.

insider's guide to things insiders don't need

Bike Rentals Pick one up at Young's Bicycle Shop, on Steamboat Wharf, because they've been there forever.

Boat Rentals Get one for an afternoon or a week at Force Five Watersports (508/228-0700) or Nantucket Harbor Sail (508/228-0424).

Real Estate You can rent a house for anywhere from $1,500 a week (you'd better request Polaroids) to $15,000. Virtually every Nantucket real estate agent is listed through the Chamber of Commerce (508/228-1700), but the one to call first is Michael Angelastro (508/228-5307).

Public Tennis Courts The Brant Point Racquet Club has the best public courts, but the courts at Jetties Beach are cheaper. Late in the season you can play at the Casino in Sconset on a first-come, first-served, leave-five-bucks-in-the-box basis.

Public Golf Rumor has it the airport once ran out of jet fuel because Wall Street bonus-mavens were leaving their Gulfstreams running while they played a round of golf. The Miacomet and Sconset clubs are open to the public year-round, though tee times aren't easy to get. In fall, you can play at the otherwise private Sankaty Head course.

Tours The longtime favorite is Gail's Tours, but consider also native islander Robert Pitman Grimes (508/228-9382), a descendant of one of the original settler families. For a more formal education, visit the fine museums run by the Nantucket Historical Association.

nantucket lexicon (or, how to sound like a local)

• The town of Siasconset is always pronounced "scon-sit."

• Sesachacha Pond is always pronounced "sack-a-juh."

• The Pocomo area begins with "pock," not "poke."

• Coatue, the scalloped spit of sand that creates Nantucket Harbor, has only two syllables: "co-too." The "co" rhymes with go.

• Madekecham is a valley and a beach, and you say all the syllables, as in "mad-a-ka-sham."

• Sankaty Head, with its cliff-top lighthouse and first views of the rising sun, rhymes with sanctity.

• Moped is pronounced "anathema."

• Martha's Vineyard is generally not pronounced.

where there's always a festival

To lure tourists year-round, Nantucket has an array of weekend festivals, including daffodil (April 28-30), wine (May 19-21), arts (October 3-9), and harvest (October 13-15). It all climaxes in the Christmas Stroll, from December 1 to 3, when residents don their winter finery and go shopping en masse. (If you're looking for a reason to visit Nantucket in November, the annual high-school football game against Martha's Vineyard is big news. You don't need tickets, but go early if you hope to find a seat.) None of the festivals are as hokey as they might sound, but neither are they sufficient reason to visit. An exception may be the film festival (June 19-24). The focus is on the scripts—a good decision, since the Gaslight Theatre (1 N. Union St.; 508/228-4435) has a screen the size of a beach blanket and the Dreamland Theatre (19 S. Water St.; 508/228-5356) is a tiny classic movie house. During the event, you'll spot twentysomething screenwriters dressed in New York black meeting fortysomething producers in pressed L.A. blue jeans for morning coffee at the Cambridge Street restaurant. You can also attend screenings—some worthy, some unlikely for a good Quaker town. Last year's hit was a documentary about a woman who slept with 251 men in one day. For tickets and schedules, call 508/325-6274.

haute wasp

Nantucket regulars have their own fashion sense, which, if you are the type to return from safari in a dashiki, you are welcome to mimic. Gentlemen wear pink pants from Murray's Toggery (called "Nantucket reds") held up by belts embellished with pictures of whales. And surely no handbag complements a cashmere sweater set and a black headband better than a scrimshaw-topped lightship basket. (When in doubt, Gucci is always acceptable.) The young here opt for a single uniform—no socks ever, Oxford-cloth button-downs, chinos—and seem bred to know their place: paradise.