IF YOU ASK A LOCAL who’s spent a lifetime on Nantucket, they’ll tell you the best time to visit Nantucket is after Labor Day weekend, when all the summer tourists and college students return to the mainland. The island is much quieter, the traffic is more manageable, the weather is blissful, and there’s something close to magical about this small island, set like a jagged jewel in the Atlantic less than 30 miles off Cape Cod. The locals often refer to the island as “Paradise” and its true Nantucket offers an incredible amount of charm with its cobblestone streets, gray-shingled cottages covered in pink climbing roses, and miles of soft sandy beaches. All of the enjoyment is there for the taking, but with a lot less traffic and people and almost everything is still open. It’s a perfect time to unwind on island time.
While Nantucket was once the whaling capital of the world, today the island is a mecca for tourism with hip new restaurants and newly built homes that are almost as common as the cottontail bunnies that roam the island. Despite all of the development, mother nature still reigns supreme: almost half of Nantucket’s land is protected (thanks to those who put the time and effort in to preserving our island), and 30 miles of bike paths wind through 9,000 acres of coastline, moors, cranberry bogs and sea-sprayed bluffs.
“Nantucket! Take out your map and look at it. See what a real corner of the world it occupies; how it stands there away off shore . . . Look at it . . .” so Herman Melville wrote of Nantucket in Moby Dick. Perhaps we shall take a closer look at Nantucket. Officially, it is all one town, but in reality there are several distinct neighborhoods. Each location will give you a good sense of what island living is all about.
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 industry. 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 sea-weathered summer retreats built in the post-whaling period.
Siasconset Village: 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 many of which still look like they did back in the day.
Madaket: Across the island from Sconset, lies Madaket – home to the famous Madaket Millie, as well as the popular Millie’s Restaurant (326 Madaket Rd.; 508/228-8435) named after “Madaket Millie” Jewett. Millie’s opened in June 2010, paying homage to the relaxed, beachside attitude so loved by locals and visitors of Nantucket. The California baja-style menu focuses on fresh, local seafood and produce and is home to the island-famous Madaket Mystery cocktail. Madaket is one of the best places to watch the sun set. On your way to the beach you will pass by the once Mr. Rogers home; the so-called “Crooked House,” which appeared to bend with the road. Mr. Rogers spent summers with his wife Joanne in this small unassuming home that his parents left him and this is what his neighbors had to say about Mister Rogers.
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.
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 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.
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.
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. If you are looking to fish alone, try below the old military reservation at Tom Nevers. Prime fishing season on Nantucket begins in early May and runs through early November. If your not sure where to go, Cross Rip Outfitters on South Water Street is among the businesses that can link you up with a seasoned fishing guide who will bring you to where the fish are. This frequently requires a journey by four-wheel drive vehicle to an out of the way beach where you will likely enjoy an afternoon with the locals. If you are interested in charters and would like more information read this article on Fishing on Nantucket.
On Nantucket, rooms are often small and prices are generally high, which gets better after Labor Day weekend. With a few notable exceptions, most of the lodging is in guesthouses built before 1900. Unless noted, the following hotels are in the heart of Nantucket (a.k.a. “Town”).
Built in 1709, the nine-room 29 Fair Street Inn (29 Fair St.; 508/257-4457) is Nantucket’s oldest hotel and restaurant dating back to 1709. Formerly known as the Woodbox Inn, 29 Fair has been carefully restored preserving its historic features including the original antique wide plank pine floors with some wooden wall planks dating back to the 1700’s. It is furnished with antiques that represents authentic Nantucket style. An old silk factory is now the Sherburne Inn (10 Gay St.; 888/577-4425 or 508/228-4425), with eight larger-than-average rooms. Conveniently tucked away in the heart of magical Nantucket’s historic district, on a quiet one-way street, the Sherburne Inn is an award winning bed and breakfast Inn which has been welcoming guests to Nantucket for over 140 years. The Hawthorn House (2 Chestnut St.; 508/228-1468) combines lovely accommodations with a superior location. Situated on Chestnut Street, in the center of Nantucket’s historic downtown area, the Hawthorn House is surrounded by many of the finest shops, museums and restaurants the island has to offer and is just blocks from the ferries. Lastly, the Old Nesbitt Inn reopened its doors as the rebranded and restored 21 Broad Street Hotel (21 Broad St.; 508/228-4749). This grand Victorian has been modernized to an urban chic style that Food and Wine calls “One of 6 amazing new retreats around the world.” This is a place where urban style embraces island sensibility in a very modern way. The interior designer Rachel Reider, and her team started with a fresh, crisp “white on white” palette, mixed with large, bold art and unexpected pops of color. Meanwhile, the common space is open, free-flowing and a space for activity that embraces the Broad Street neighborhood. For a full list of places to stay click here.
After a few seasons at Wade Cottages (35 Shell St., Siasconset; 508/257-1464; three-night minimum), you’ll feel as if you’re returning to your family compound. These charming accommodations offer eight rooms, six apartments, and three cottages. With spectacular waterfront vistas, spacious lawn, and direct access to the pristine beach below — all within easy walking distance of the village — the Wade Cottages are perfect for a long weekend or perhaps a wedding venue. Weddings can be held at the Cottages from late May through mid-June, and mid-September to mid-October. The lawn can accommodate a reception tent for up to 150 guests.
The Wauwinet (120 Wauwinet Rd., Wauwinet; 800/426-8718 or 508/228-0145) is luxury at its finest. One of the first resorts built on the island, it is Nantucket’s only member of the prestigious association of Relais & Châteaux. A charming blend of history and sophistication, the Wauwinet offers breathtaking landscape and views, historical architecture and a wide array of amenities like bicycles, kayaks, croquet, tennis courts, and sailboats. The Wauwinet is recognized worldwide for its impeccable service, outstanding cuisine and luxurious accommodations. Some of the 35 room are small but cozy so if you need a little more space make sure to book the right room. On a bluff in Sconset there’s the most romantic getaway: Summer House Cottages (17 Ocean Ave., Siasconset; 508/257-4577). The 10 rooms are really self-contained little rose-covered cottages, all arranged around a garden. The Cottages are decorated in a simple, timeless English cottage style and the ocean beach and heated fresh water pool are nestled by the dunes just below the bluff. Two award winning restaurants complete the property, offering al fresco dining facing the ocean next to the pool for lunch and dinner at the Beachside Bistro and the renowned Summer House Restaurant and piano bar for nightly dinners at the top of the bluff.
At the Boarding House (12 Federal St.; 508/228-9622), 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 less expensive bistro menu. The dining room of Topper’s (508/228-8768), 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. For lunch order the Lobster roll, chowder and champagne – it’s delicious!
Nantucketers love the Club Car (1 Main St.; 508/228-1101), 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 The Pearl (12 Federal St.; 508/228-9701), which has a tropical-aquarium theme and requires reservations. This island gem created by Seth and Angela Raynor, is focused on current coastal cuisine showcasing seasonal shellfish and seafood, produce from Island farmers and heritage meats. Executive-chef, Seth Raynor creates a seasonally changing menu that showcases modern translations of exotic flavors inspired by off-season travels. The Pearl’s signature entrée, Salt & Pepper Wok Fried Lobster, is considered to be the Island’s best lobster dish and Travel & Leisure magazine gave it a World’s Best Award. The Pearl was also awarded The Best Seafood Restaurant in all of New England, by New England Travel & Life. The Yellow Fin Tuna Martini is considered one of the best appetizer on the island. Another new restaurant is The Nautilus (12 Cambridge St.; 508/228-0301) This buzz-worthy restaurant made its way to the top of the list for locals and visitors alike. Inspired small plates culled from various culinary traditions and countries translate into mouth-watering dishes to share. Don’t miss the best calamari you will ever taste, and, if there are 4 or more in your party, try the Peking Duck. It’s simply marvelous!
A few blocks from the busy center of town but still in the historic heart, American Seasons (80 Centre St.; 508/228-7111) exudes warmth, particularly in the chilly shoulder season. The menu is imaginative “haute humble” cuisine featuring what’s seasonal, local and lush. They offer an exceptional American wine list and are consistently the most buzzed about Nantucket restaurant. Hands down. Find out whether or not you and your date are compatible at the Company of the Cauldron (5 India St.; 508/228-4016): the lights are low, the tables snug, the mood intimate. Cape Cod Life said it best, the Cauldron exudes a “darkly handsome, romantic-as-a-novel” atmosphere. Limited menu features daily special items prepared with care and skill.
For French in the classic style, there’s The Chanticleer (9 New St., Siasconset; 508/257-4499). One of the most romantic destinations on the island, you may linger over an intimate lunch in the Rose Garden or come together with family and friends for a convivial dinner or dine al fresco on warm summer evening. The lush gardens produce organic herbs, flowers, berries and seasonal vegetables for the kitchen. An extensive wine list features some of the finest wines in the world. The main dining room feels more like a country-club banquet hall, but regulars know to ask for seats in the handsome bar, where the presence of smokers makes it all the more French.
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) is casual. Breakfast is the specialty, though the coffee is a tad pedestrian. Another local favorite is The Downyflake Donuts, which serves some of the best fresh, warm out of the oven delicious donuts. Did we mention delicious?
Crowds flock to The Juice Bar (12 Broad St; 508/228-5799) for homemade ice cream & waffle cones plus healthy juice. During the summer there is often a line right out the door and around the corner of The Sunken Ship but it’s worth the wait on a hot summers day!
With a few exceptions, the best shops lie in the historic heart of Nantucket; along Main Street, the Wharfs, Federal Street, and Centre Street. Let us know which stores you liked the best and why.
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 Susan Ottison Basket Shop (170 Orange St.; 508/228-9345) and Nap Plank, who runs Nantucket Basket Works (14 Daves St.; 508/228-2518). The Nantucket Lightship Basket Museum; (49 Union St., 508/228-1177) displays a seemingly infinite variety of restored antique and contemporary baskets, ranging from simple, small circular baskets without lids, to ornately embellished purses on the larger side.
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, Island Cashmere (32 Centre St.; 508/228-7611) is your savior.
The best presents come from Anderson’s (29 Main St.; 508/228-4187) a boutique which features the finest in Nantucket inspired gifts, furniture, lighting, serving ware, linens, and home accessories with a sea side chic style specific to Nantucket. Many of their pieces are custom made and only available in their store or online. 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). Almost everyone stops at Nantucket Looms (51 Main St.; 508/228-1908) to see their beautifully woven throws, if not to buy handmade sweaters. And while you are on Main Street don’t forget to take a picture in front of Gardiner’s Corner, a giant sign with distances from Nantucket to various points around the world. This is a good keepsake memory to share with family and friends.
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).
There are plenty of reasons to visit Nantucket, but surrounding all of them is a sandy boundary between sea and land. Virtually all the beaches on Nantucket are open and easily accessible to the public.
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.
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) Jeeps. 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 looks a bit like a tailgate party.
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 Cours 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.
To lure tourists year-round, Nantucket has an array of weekend festivals; including the Daffodil in April, the Nantucket Wine Festival in May, the Figawi Regetta on Memorial Day Weekend, the Film Festival in June, the Opera House Cup in August, and the Arts and Harvest in October. 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. And last but not least Christmas Stroll, which is the first week of December, when residents don their winter finery and go shopping en masse. For a full list of annual events click here.
Nantucket regulars have their own fashion sense – laid-back, casual and comfy. Gentlemen wear “Nantucket Reds” – pink pants from Murray’s Toggery 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. The young here opt for a single uniform—no socks ever, Oxford-cloth button-downs, and chinos (a.k.a. the preppy look).