An Insider's Guide to the Islands

Preppy plaids and pearls, haute cuisine and history — Nantucket.

Where to stay

Getting a car to Nantucket is no small feat. Even if you manage to snatch a rare weekend ferry reservation for your vehicle, you have to be willing to brave the steep transport cost and the two-plus-hour ride over on the slow boat.

But who needs wheels, anyway, with so many great places to stay right in town? About 30 paces from the lower end of cobblestoned Main Street is the Union Street Inn ($95-$350 a night), where a recently completed renovation gives off the sophistication of Manhattan crossed with the old-money charm of Greenwich. Perhaps it's because Ken Withrow, who runs the inn with his wife, Deborah, lived in the latter while working in the former, as general manager of the sleekest of New York's boutique hotels, the Royalton. The city's loss is the island's gain: The Union Street's 12 rooms showcase the best of what remains of 1770 (wide-plank floors, crooked walls) with stylishly antiquated décor — toile wallpaper, four-poster canopied beds, even real wood-burning fireplaces in six of the rooms (usually verboten in any property, let alone a 230-year-old one). Bonus: Hot breakfast each morning — such as omelets and croissants, plus a cold buffet of fruit, yogurt, and juice — is included in the rate and served on the tree-lined outdoor patio.

You may have heard of her shoes, but now Vanessa Noel has entered the lodging business, too, with the purchase of what used to be the Quaker House Inn downtown. The new Vanessa Noel Hotel ($340-$480) sits above her eponymous shoe store (moved from its previous island location on Orange Street), which also hosts jewelry trunk shows throughout the summer. The eight rooms tucked upstairs are SoHo meets beach: sand-hued and loaded with Bulgari amenities and Frette linens and slippers. What used to be Kendrick's restaurant at the Quaker House is now a bar with leopard-print banquettes and upscale light seafood nibblies (smoked salmon, gravlax, caviar, and the like) from Caviarteria in New York.

Down the road, the Harbor House Village (from $325) is undergoing some changes of its own. All the rooms were renovated over the winter to give it a “very Nantucket feel.” The hotel consists of two separate houses, each dating to the 1800s, and six townhouses on South Beach Street. This summer, a new Chinese restaurant goes in: Harbor Wok, related to the Wok restaurant in Wellesley. The White Elephant, around the corner, is a 65-room full-service resort fronting the harbor ($440-$1,380). It received its own facelift two years ago, adding the Brant Point Grill, a lobster, steak, and seafood restaurant with a raw bar and alfresco seating on the water.

For something more remote, there's the Summer House ($550-$900), a little-known collection of cottages in 'Sconset that compose one of the island's most unusual getaways. Miniature shingled outbuildings ring a central lawn and garden; each cottage is little more than a glorified freestanding bedroom, but each has English country pine furnishings, a tiny Adirondack lawn chair, and an overflowing window box. Inside the main house, there's a full restaurant and piano bar, and across the street, a pool perched at the ocean's edge. Three years ago, the hotel snapped up two houses in Nantucket Town to create in-village satellite properties for guests who'd rather stay within walking distance of the island's shops, galleries, and restaurants.

Where to eat

BlueFin restaurant replaced one of the island's beloved nosheries, Nantucket Tapas, which you'd think would engender local resentment. But it weathered its first full winter — bravely staying open year round — and won warm reviews from the natives. That's due in part to the insider status of co-owner Jonas Baker, who did time behind the stoves at the Galley and the Nantucket Golf Club, and rolled sushi at Nantucket Tapas (where he told its owners, “If you ever want to sell . . .”). To renovate the place in just seven weeks last year, he and partner Rick Craveiro cashed in about “10 years' worth of favors” with local construction and fisher folks, which also accounts for the fresh striped bass, yellowfin, and bluefin that show up on his doorstep these days.

Also new in town: Even Keel, in the Main Street digs of the old Espresso Café. The Keel serves three meals a day and offers full-service table seating in addition to the takeout that defined the old spot. The colors indoors are soothing, but the garden patio out back is the place to be.

Not new but still terribly hip is the much-talked-about Oran Mór. From the looks of the menu, you'd think the place would have an edgier ambiance. After all, items like tofu and shiitake chow mein with yuzu dressing aren't exactly old Yankee fare. But this isn't exactly a predictable place. Climb the copper-lined stairs leading to the second-story restaurant, and you'll enter a series of rooms that look like the sort of place where whaling-ship captains would have celebrated big returns after a few years at sea. Then there's the menu — salmon with soba risotto and edamame? Indian curried shrimp with Urfa pepper spaetzle? But it works. And you'll be booking a table for the following night before your heels hit the copper on the way out.

Also still on the hot list: the aquatic-themed Pearl restaurant on Federal Street. Chef Seth Raynor and his wife, Angela, serve French-Asian fusion dishes such as their signature salt-and-pepper lobster wok in a setting that, though it's more South Beach than Nantucket, still works.

Don't-miss takeout

When you want to take your food and run, there are some prime spots on Nantucket to pick up your provisions. One of them is, in fact, Provisions. Located right on Straight Wharf at Harbor Square, this veteran has been loading up picnickers with sandwiches and groceries for 22 years. There are even a few tables if you can't wait until you hit the sand.

A few blocks away is its prime competitor, Something Natural. Here, in a ramshackle building just outside the heart of town, weather-beaten preppies line up on the porch and wait for hearty sandwiches, which they'll pack in their Jeeps and take out to Surfside Beach. Alternatively, grab a bite at the island's best takeout secret, the snack shack at Surfside, which some swear grills the best burgers on Nantucket.

For gourmet supplies for your summer rental, Fahey & Fromagerie on Pleasant Street is the place to stop. Along with the wines (many for $15 or less), there are imported cheeses, olives, and oils, plus takeout sandwiches. Pizza maker Evan Marley is just back from a trip to Naples, and his thin-crust pies are the best on the island.

For the freshest and healthiest raw materials, head out to Bartlett's Ocean View Farm, off Hummock Pond Road. This is the island's definitive farm stand, selling everything from plants to gourmet entrées, soups and salads, breads and pies. Also available, starting at 8 a.m., are breakfast pastries and juices.

Which leads us to the subject of mornings. Downy Flake — just outside of town, en route to Madaket — is an island institution, not just for its ungodly opening time (5:30 a.m.) but for its dedication to doughnuts made the old-fashioned way. It sells only three varieties, chocolate, sugar, and plain, “but when they're this fresh, you don't need anything fancier” — or so says our cabdriver, a 45-year Nantucketer sporting a threadbare sweater and Ray-Bans.


If you're an antiques aficionado, the latest entrant to town (or just outside of it) should be a must-stop. L & E Reid Antiques & Fine Wine marked its debut this summer with two container shipments from France. The new store is located at 39 Washington Street, the baby of Linda and Everett Reid. But because the couple had previously been in the restaurant business — they ran Moona, then American Seasons — they have been collecting wine for years. The furnishings will focus on American and French styles; wines will be poured in scheduled tastings, with personal consultations available by appointment.

For the canine connoisseur, a new shop called Sandy Paws has opened at 20 Centre Street and is Nantucket's answer to the Vineyard's ubiquitous Black Dog. A gourmet dog-treat counter features savories behind glass, and there are wooden barrels of biscuits in flavors that make Milk-Bones look as pedestrian as Twizzlers (from bacon to Cape Cod cranberry, $4.25 per half pound), plus all the requisite accessories: dog bowls and pottery, Frisbees and balls.

The best island shops don't change much, especially in the heart of town, where consumer loyalty to old favorites runs as high as the rents. For women's clothing, the favorites are Zero Main and Hepburn, with classic yet au courant specialties ranging from buttery-soft suede jackets to sassy shin-skimming capris. If you're still lamenting the loss of Cashmere Boston on Newbury Street, dry your tears: Its sibling, Island Cashmere, still offers a fine twine or two.

Top off your look with a lid from Peter Beaton Hat Studio, the exclusive milliner with an everyday aesthetic. Designer Darcy Creech first made a name for herself back in the early '90s, parading her creations in the island's annual Daffodil Festival parade. A few years later, she designed Hillary Clinton's blue inaugural hat (mocked by some for making Hillary look like Paddington Bear). Creech's shop at 161/2 Federal Street has expanded the line to include handbags, sunglasses, and chic summer slides. There are more than 75 styles of hats in more than 10 brim shapes, with your choice of interchangeable grosgrain ribbons.

For home accessories, the first and last word is Nantucket Looms. This shop is half showroom (downstairs), half artisan studio (upstairs), and fully an island institution — it's been around for 35 years. It sells handmade blankets, jackets, paintings, jewelry, and pottery — pretty much anything you need for an upcoming occasion or self-indulgence. (Who has time to shop for this stuff at home?)

One Man's Junk

Yard saling — yes, that is attending yard sales — is a high art here. Each weekend a small bevy of islanders, and some visitors in the know, tackle the sale circuit with the zeal of sports competitors. And with good reason: The cast-off belongings of old-money homeowners can yield such treasures as signed first-edition books. They're also a good source of bulky furnishings for on-island homes (e.g., tables, chairs) that would be difficult to get on and off the island via ferry if they had to be purchased on the mainland. Conventional wisdom holds that summer is the peak season for sales, but that's just when they're the most crowded. Most are held in the fall when people move on and off the island. To “do” the sales right, pick up a copy of the Nantucket Inquirer and Mirror, available on Thursdays, and map out your sale route based on opening times and location.

After Dark

Still standing? Favorite nighttime hangouts on Nantucket include the Ropewalk, a glass-walled restaurant and bar at the end of Straight Wharf that's buzzing with yachties; the Boarding House, atwitter with intoxicated twentysomethings; the Club Car, a piano bar in an antique railroad car, populated with martini minglers of all ages; and the bar scene at the restaurant 21 Federal, specializing in the over-30 investment-banker set. For live entertainment, the Chicken Box (or “the Box”) has bands every night; the Muse is the island's hottest nightclub and concert venue; and the Brotherhood of Thieves is a subterranean pub in town with intermittent guitarists or folk duos.

Ultimate picnic

If you have a four-wheel-drive vehicle, this is the place to go, according to island regulars who only reluctantly deliver up the secret: Grab sandwiches and head to Smith Point near Madaket Village, which occupies the western point of Nantucket. It's possible to walk out to the point, but that's a trek of more than a mile on soft sand. Instead, get a beach permit from the police department (20 South Water Street, 508-228-1212, 8 a.m.-3 p.m. daily for permits) for $50 for nonresidents. Most 4WD rental vehicles come with the sticker, but call the rental agency first to be sure. Tip: Time your visit for sunset to be rewarded with the ultimate views.

Celebrities and laid-back charm, beaches and natural beauty — Martha's Vineyard.

Where to stay

Tucked into the trees above Menemsha Harbor, the Beach Plum Inn is one of the new lodging hot spots on the island. But it isn't new: The inn was built in 1898, constructed with wood salvaged from schooners that were destroyed in a brutal November storm. In December 2000, the main house was ravaged by a fire that consumed everything but the kitchen. Now the inn has reopened after a complete restoration.

Perched on six acres, with views of the harbor, Vineyard Sound, and the Elizabeth Islands, the gray-shingled inn has 11 rooms that are pleasantly simple, if a bit less stylish than in their prefire days, painted in pastels and accented with floral fabrics and somewhat fussy pillow-covered beds. (We counted seven pillows on ours.) The tab also includes a priceless amenity: a pass for private Lucy Vincent Beach, the island's most gorgeous stretch of sand. The headliner here is the view from the restaurant, with two walls of windows overlooking the lawn, patio, and harbor. A full hot breakfast is made to order and comes with the price of the room ($250-$400 a night). Time your dinner for sunset — if you can clinch a reservation, that is, among all the non-guests claiming the seats.

In Edgartown, there's an exclusive new four-bedroom residence one block off Main Street run by one of the most chic and successful inns in town. Thaxter House is owned by the neighboring Hob Knob Inn, and if it's good enough for Paul McCartney's clan (McCartney rented it for his nephew's wedding last fall), it's probably sufficient for yours. The house was fully renovated last year and is the epitome of country charm. Think plantation shutters, mismatched but complementary upholstery, and a beadboard and stainless-steel kitchen, with an antique distressed dining table that seats eight. Each of the bedrooms has its own fireplace, bathroom, and private deck or porch. (Paul stayed in the one with the taupe handmade quilt, upstairs.)

If you can't afford the Thaxter House's $10,000-a-week peak-season price tag, the Hob Knob is the next best thing ($250-$525 a night). The work of the same interior designer, the inn's 16 rooms are styled with English chintz, American and British antiques, and collectible porcelain plates. Each door is handpainted with a mock porcelain plaque bearing the room number and a cow, with a miniature outline of the island hidden somewhere in its spots. The cow motif throughout the inn is no mere affectation but a reference to the live herd that owner Maggie White keeps on her farm in West Tisbury.

Where To Eat

In Oak Bluffs, the newest dining spot is the Park Corner Bistro. This intimate 28-seat restaurant across from the Offshore Ale Co. has all the charm of a European cottage, with its whitewashed ceiling, ocher-red walls, dried flowers, and black and white photography. It serves three meals a day year round, with highlights such as vichyssoise, beet salad, and duck breast with blueberry jam. Co-owners Jesse Martin and Josh Aronie have just snagged a liquor license and have added a bar in a speedy renovation.

The restaurant still claiming the biggest buzz on the island is Atria, now in its third season at the location formerly home to Water restaurant on Main Street in Edgartown. The leopard-print lounge with live entertainment is still there, but the menu now has a decidedly Asian twist. Mussels are served with lemongrass, coconut, and fresh chiles; lobster is wok-seared and served whole in the shell over mashed potatoes.

Don't-miss takeout

If you're lucky enough to be staying somewhere with kitchen facilities, there are critical fixings available for any cookout. Start the meal with a heaping serving of country ribs from Shiretown Meats on Main Street in Edgartown. The pork is fall-off-the-bones tender; the sauce, Cajun style, tangy-piquant with just a hint of sweet. You can load up on any kind of meat you'd like to sizzle on the grill, plus sandwiches, gourmet supplies, and sauces. The prime spot for lobsters and littlenecks on the Vineyard is Larsen's Fish Market in Menemsha — not just because it's right on the docks where the old crusties unfurl their nets, but also because it's the most pleasant place to pass a presunset hour. (If you can't get to Menemsha, the Larsen family also owns the Net Result in Vineyard Haven.) On the way out, stop at the Menemsha Blues clothing shop to snag a shirt with the trademark bluefish, which has become more of a cachet icon than that now-clichéd black dog.

For fresh produce, two farm stands are a must: Norton Farm on Edgartown/Vineyard Haven Road, just past Windfarm Driving Range if you're coming from Edgartown, and Morning Glory Farm, on West Tisbury Road en route to the airport at the intersection of Meshacket Road. Polish off the meal with a pie from Eileen Blake's Pies — apple, apple crumb, blueberry, peach, strawberry rhubarb, pecan, or lemon. This woman knows from crust: For the past 30 years, she's been turning out nearly every variety you can name — about 120 of them a day in high season — sold from a gazebo in her front yard on State Road in West Tisbury. Look for the big white sign with black letters, not far past Cronig's Market.

Anyone who's an aficionado of breakfast pastry heads to Humphrey's for doughnuts. Real arterial-trainwreck riches await here: apple fritters; crullers; and old-fashioned cake, glazed, chocolate, bavarian cr쳌me, and the puffiest jelly-filled doughnuts you will ever taste. There are also cookies, muffins, loaves of bread, sandwiches, and fresh coffee. (For those staying down-island, there's a new Humphrey's location on Winter Street in Edgartown.)


Two things are constant on the Vineyard: There will always be the new, hot, and trendy, yet certain institutions will endure. This year, however, an unlikely one went down — Fligor's, the buy-everything gift shop on North Water Street in Edgartown. Newly ensconced in its place this season is an outpost of Murray's, the Nantucket department store that's home to the famed faded Nantucket Reds line of clothing and also sells men's and women's designer wear such as Ralph Lauren and Lilly Pulitzer. The shop's lower-level children's department remains, under separate ownership and with a new name: Vineyard Kids. Even if you don't have tots, it's worth a trip to stock up your rental house with badminton and volleyball sets, Frisbees, and water guns.

Also in Edgartown, Sisters Too has opened on Winter Street, selling the sorts of country-chic home accessories — pottery, planters, and copper cookware — that fill the second and third homes of the summer set. If you're fortunate enough to be houseguests of the aforementioned set but neglected to bring a gift, make a stop at the new L.A. Burdick Handmade Chocolates shop on South Water Street (where the old Espresso Love used to be). Show your gratitude with a box of cognac truffles and perky little chocolate mice. Or tuck into one of the café seats, order up a cappuccino, and forget about your pretentious hosts altogether.

Speaking of Espresso Love, it hasn't disappeared, only moved. The coffee shop has moved to the former site of Savoir Faire restaurant on Church Street, clinching the cushy outdoor patio space.

Do as the insiders do

There are a few activities that make Vineyarders' calendars each year but rarely make it into the guidebooks. The annual Possible Dreams Auction is one. For 23 years, humorist Art Buchwald has emceed this event to benefit Martha's Vineyard Community Services, a coalition of six charitable programs. For $20, everyday schmoes can attend and bid on incomparable experiences. This year's lineup includes a tour of John Quincy Adams's house with author David McCullough, golf with Vernon Jordan at Farm Neck, and a lunch cruise with Bob Vila on his boat. The auction will be held on Monday, August 5, in the garden of the Harborside Inn in Edgartown.

At the other extreme, the annual Agricultural Fair is authentic old-time stuff — 141 years and counting — with livestock shows, a carnival, and food vendors. This year's dates are August 15-18, and it's worth the price of admission ($7 adults, $5 seniors, $4 juniors) just to check out the exhibits and crafts in Agricultural Hall, a 100-year-old barn that was taken apart in New Hampshire and put back together piecemeal in a communal barn raising in 1994.