Nantucket
Overview

With cobblestone streets, thoroughly American lighthouses, and a one-of-a-kind whaling museum, Nantucket has become the charming but chic must-visit summer colony. Once an only-in-the-know tony destination for High WASPs and well-heeled ‘weekend warriors’—the New York 20 and 30-somethings who managed to make it every weekend (fog be damned!)—it is now the low-key glamour destination for the New Yorkers that are totally over the Hamptons. Think politicians (Bushes, Bidens and Bill), editors, fashionistas, socialites and the investment bankers they date, who don't want to actually be seen. Except on their Instagram feeds, of course. (#ACK #blessed) And as history has shown wherever a New Yorker goes the anti-Hollywood, casual celeb will follow — ahem, Meryl Streep and Drew Barrymore. Even a Kardashian tried to escape the spotlight on Nantucket, unsurprisingly attracting more attention. Thanks, Kourt. But even a reality star can't keep us away from the piping plover loving pristine beaches. So, put on your preppiest stripes (MDS Stripes and La Ligne will suffice), don’t forget to pack a classic one-piece (Lisa Marie Fernandez and Solid & Striped for good measure), and get ready for an idyllic New England escape.

Founded by the British in 1641, the salt-sprayed "Grey Lady" is a former whaling town rich in history with 82 miles of quintessential New England coastline. The town of Nantucket, basically anything near Main Street, is the perfect place to learn a lot in little time. Because, let's be honest, the beaches beckon. Before the mid-day rush hour, putter down Main Street to the harbor and wander the small side streets on Old South Wharf. But here's the thing about Nantucket: it's a place where you must know the insiders' itineraries to truly experience all she has to offer. Historic architecture and un-touched natural beauty (in 1966 the island was designated a National Historic Landmark); fine dining, killer martinis as big as a whale at The Wauwinet and hangover-helping Downyflake donuts; three dollar rope bracelets (the ultimate summer status symbol) and thousand dollar Nantucket Lightship Baskets. Your days will be spent driving the endless dirt roads to the picturesque beaches providing an endless panorama of the crisp, blue sea...

Stay

Where to stay

Indulge

Indulge

Famed restaurant Black-Eyed Susan's is a non-negotiable. As mentioned it serves arguably the best blueberry pancakes (on earth) that are loaded with fresh berries and served with REAL maple syrup – they’re simply TDF. Sit inside to watch the chefs flip them on the griddle. If you are further from town, skip the morning traffic and go for dinner. Note the restaurant is BYOB and walk-ins only; while waiting for your table send friends to Murray's Beverage Store on Main Street for wine, thank you, Hayley.  For seafood, sunset, and sand Galley Beach (aka The Galley) is #1 and is set right on the sand of Cliffside beach. Be sure to allow time to sit on the beach with a cocktail before dinner. For more laid-back beach vibes, picnic tables and sunset views, Millie’s is an island staple serving simple, flavorful fresh fish tacos.  Cozy up at Chef Marcus Ware’s Restaurant at the Greydon House, where updated American classics is right on theme—just make sure to get the Lobster Broth appetizer to start. The Nautlilus is a rustic-modern hot spot that serves global, seafood-centric small plates & inventive craft cocktails. Top tip: order the whole roasted peking duck! The Club Car has long been another island staple for grabbing a grilled cheese or a cup of chowder — but thanks to a recent modern makeover, it’s now full of ferns, soft blue booths, and servers popping bottles of rose to wash down a menu full of super-fresh seasonal small plates. The super-casual Pi Pizzeria is the mid-island go-to for mouthwatering wood-fired Neapolitan-style pizzas.  If fancy tinned fish is up your alley, get your fix at Afterhouse, a charming subterranean spot that serves natural wines alongside the silkiest, most exquisite tinned seafood – like white tuna belly from Spain and spiced sardines from Portugal. (They also serve fresh seafood dishes like a Tuna Tartare Sandwich and a Lobster Roll on challah with lemon aioli!).

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If town is the heart of the Grey Lady, Sconset is its soul. Misty mornings call for dreamy beach walks while seals swim along the shoreline. Bicycles rest on picket white fences which frame the idyllic shingle cottages with their climbing pink rose bushes — an utterly iconic Nantucket image. Claudette's sandwich shop exemplifies the sweet, simplicity of the village with a menu of just eight sandwiches all served with her secret savory sauce. Follow lunch with a trip to the Sankaty Head Lighthouse — an easy, breezy 2-mile bike ride away. Top off the day with a candlelit dinner at the award-winning TOPPER's restaurant at The Wauwinet. Order from the à la cart menu featuring locally grown produce and regionally caught seafood. Post dessert — kick off your heels on the bayside deck for the famed peach-tinged vodka Wauwinet-ini.

Cisco Brewers at Bartlett’s Farm is an ACK right-of-passage: it’s a rustic brewery with live music, tasting & tours – along with 3 bars serving craft beer, wine & other cocktails. Housed in a vintage railroad car, be sure to arrive early at The Club Car Restaurant & Piano Bar and snag a spot near the piano. Stare out at sparkling water, beautiful boats and even more beautiful people as you perch up at the quartzite-topped bar at Cru while the pink pours seem to flow freely. For the most dedicated visitors the nightlife scene can be summed up in three words: The Chicken Box. This legendary bar has been hosting musicians for decades. A little, dark, a little sweaty not a blue blazer in sight — it’s a little bit of heaven. Planning your trip around a Chicken Box reggae concert is not that bad of an idea. If you are with a big group and want to keep to yourselves grab a giant corner tables at The Tavern. You'll go to smoke a ciggie and try to hop the fence to get back in and it won't go well. Trust us. Keeping things as prim and posh as possible the line for the idyllically window-paned Straight Wharf Restaurant starts forming just after 9 pm. Epic hits from the 80s and 90s along with "the" song of summer 2018 along with the Goombay Smashes make for a raucous crowd of preppies. This is where you'll finally find the hottie you made eyes with at the airport while waiting for your ubiquitous monogrammed L.L. Bean boat and totes. Ties will get loose and cashmere cable knits will come off. Guaranteed. Fortunately, the most important nighttime note you will learn the first night and never forget: stilettos and cobblestones do NOT mix. Ever.

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Explore

Explore

With its slow pace and relaxed vibe, Nantucket has always been a go-to destination for generations of families. If you're with children Jetties Beach is an ideal. Mellow waves keep the kids happy and in the water, a cafe-filled boardwalk keeps them fed and to be totally straightforward, public bathrooms are a huge plus. A weekend to Nantucket calls for eating your heart out, so head into town to stop by The Juice Bar for a chocolate/vanilla twist soft serve cone — with sprinkles, of course! Nantucket is not only known for its beaches but also for its picturesque biking paths some. Ride Milestone Road Path to pass one of the largest nature reserves, which you’ll swear, is the Serengeti. Reserve bikes with Young's ahead of time and take a page from Hayley Bloomingdale's book: "I always do a long bike ride to Madaket Millies; first stop at Madaket beach to take a quick dip, then order fish tacos with cold beer and soak up the sun before biking back." Now you're almost feeling like a "lifer"! Make time to set sail on the Nantucket Sound with an unforgettable experience with Endeavor Sailing. On one of the inevitable foggy days, head to iconic sandwich establishment Provisions, located in the harbor. Order the legendary Turkey Terrific sandwich, essentially thanksgiving dinner between two slices of Nantucket's famous and freshly baked Portuguese bread. When cocktail hour arrives (11 am on) head to The Gazebo for its notorious frozen mudslide. For the golfers of the group: hit up the links at Old Sconset Golf Club, founded by none other than the Coffin family.  It’s one of the first 100 courses in the country and believed to be the longest privately held course today book ahead of time. Be sure to visit Siasconset market for their epic carrot-cake post play.

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If swarms of blonde prep-schoolers in polo shirts, collars up(!), isn't your ideal holiday then you should visit Nantucket during the off-season: Labor Day to Memorial Day. You'll beat the crowds and still realize the majestic splendor of the Grey Lady. The Nantucket Wine & Food Festival held mid-May makes for a perfect adults-only vacation. There's everything from Veuve-Cliqout-filled VIP events to fresh lobster lunches at iconic establishments and to truffles & tastings with live music.  For the die-hards who are willing to embrace the Nantucket frost (to put it lightly), the most magical Nantucket experience is the annual Christmas Stroll. On the Friday following Thanksgiving, hundreds of twinkly lighted, hand decorated, seven-foot Christmas trees line Main Street. The event is kicked off by an opening ceremony complete with carolers and cocoa. After sharing your gift list and singing your good graces to Santa, be sure to visit the Whaling Museum, which turns into a glittering wonderland. Warm up with hot toddies at Greydon House, you're going to need them!

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SHOP

Where to Shop

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First things first: you always must dress the part. Think of the Nantucket as a super-inclusive elite New England country club where there is an unspoken dress code to follow, i.e. boarding school. Vintage Lily Pulitzer if you dare, linen button-downs, the prettiest dresses you own (current designers allowed) and, of course, a good stripe. Basically, start stalking the Instagram accounts of Moda Operandi's Hayley Bloomingdale and former Voguette Cynthia Cook Smith — the go-to Socialite wedding planner who, needless to say, got married on Nantucket. Play on prep with Jil Sander's soft and subtle ginghamsBrock collections breezy, romantic dressesoversize pastel Acne sweaters paired with Saint Laurent's neutral day to evening flats. As the warm evening light sets in and a chill comes to the air put on white jeans and over-sized cashmere sweaters while the boys pick up lobster dinner-to-go from Sayles Seafood for a beach dinner at Great Point on the northernmost point of the island. #ACK #blessed

Murray's Toggery Shop, the 70+ year-old store, on the top of Main Street is where you stock up on the staples — Nantucket reds (the only retailer with authentic originals), fisherman sweaters and, of course, the tennis whites you forgot to pack. From there, head across the street to Erica Wilson home to one of the best Eres swim selections whose clean lines and cool tones exemplify the subdued glamour of the Nantucket scene. Drop into Skinny Dip to get all the essentials you'll ever need for Nantucket.The classic navy with white "Nantucket" sweatshirt is all you really require but you'll only learn this next summer. CJ Laing has the perfect caftans, scarves and accessories. Pick up a pair of Rebecca de Ravenel shell earrings to pair with your Natalie Martin dresses. And for the final Nantucket status symbol, a Something Natural T-Shirt — the older it is, the cooler you are. 

Shop the Destination

Zimmermann Iris Smocked Bodice Maxi Dress $615.00
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Lizzie Fortunato Rome Pink Hoops $95.00
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Alexandre Birman Clarita bow-embellished linen sandals $595.00
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Rosie Assoulin Embellished woven straw tote $695.00
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Marysia Corsica bandeau bikini top $150.00
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Marysia Corsica high-rise bikini briefs $155.00
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FRAME Le Cutoff Forton Shorts Denim $198.00
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Ancient Greek Sandals Thalia calf hair and leather sandals $215.00
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FAITHFULL THE BRAND Le Petite Button Front Dress $190.00
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LoveShackFancy Mia Cropped Ruffled Floral-print Cotton Top $215.00
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LoveShackFancy Tiered floral-print cotton mini skirt $255.00
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Ahlem Concorde Sunglasses $470.00
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Melissa Odabash Jordan Lace-up Gingham Bandeau Bikini Top $110.00
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Melissa Odabash Jordan gingham bikini briefs $110.00
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Nightcap Clothing Eyelet Apron Dress $495.00
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Cult Gaia Luna bamboo basket bag $218.00
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The East Order Emilia Mini Dress $225.00
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Simon Miller Bonsai White Leather Mini Bucket Bag $390.00
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Lisa Marie Fernandez Tie-waist linen top $475.00
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Lisa Marie Fernandez Polka dot-print tie-waist linen skirt $690.00
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Emilia Wickstead Roxane halterneck swimsuit $325.00
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Emilia Wickstead Leslie high-waisted linen shorts $440.00
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Caroline Constas Lyssa striped cotton-blend dress $495.00
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Le Specs Revolution round-frame metal sunglasses $79.00
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Muuñ Lou striped-canvas and woven-straw bucket bag $190.00
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Alexis Calypso Ruffle Mini Dress $450.00
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Rebecca de Ravenel Ophelia shell clip-on earrings $272.00
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HVN Morgan Gingham Silk Crepe De Chine Midi Dress $625.00
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Carrie Forbes Salon Woven Faux Raffia Slides $300.00
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HEREU Cabas Leather-trimmed Straw Tote $335.00
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J.Crew Marseille Striped Linen Jumpsuit $130.00
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Yestadt Millinery Fringy White Fedora $345.00
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Castañer Carina canvas wedge espadrilles $96.00
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Haight Striped Triangle Bikini $190.00
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Caroline Constas Andros off-the-shoulder shirred gingham bikini $315.00
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