Nantucket Guide

design darling nantucket guide

There’s no more charming place in the world than Nantucket and the island has long held an especially dear place in my heart. My parents have owned a home on Nantucket for most of my life and my family’s history on the island dates back to the 1880s. My husband and I were married in the ‘Sconset Chapel in 2017, thirty-one years after my parents said “I do” in the same spot. We spend as much time there as we possibly can and love frequenting our tried-and-true favorites and trying out the new spots that open every summer. Below are my favorite restaurants, hotels, beaches, boutiques, and everything else I can think of to help you plan a trip to this magical place. I’m confident these recommendations will have you falling in love with Nantucket too!

Lunch/Dinner

  • Boarding House

    I love a lively group dinner outside on the Boarding House patio. Located in the heart of downtown on the corner of Federal and India Street, it’s a perfect spot for people-watching and a plate of their lobster spaghetti.

  • Brant Point Grill

    If you’re looking for an Instagram opportunity alongside your meal, head to this restaurant located outside the White Elephant for its sweeping views of Nantucket Harbor. Don’t leave without trying a bite of their famous lobster mac and cheese.

  • Brotherhood of Thieves

    A casual, family-friendly spot for burgers and lobster rolls. The downstairs interior has the feel of an old whaling bar and is a cozy spot to sit by the fire on a rainy night, but if it’s warm out we always ask to sit in the outdoor patio to the left of the main entrance. It’s a no-frills hangout where no one will rush you out of your seats, plus it’s a two-minute walk down the street to cult favorite Juice Bar for ice cream.

  • The Chanticleer

    An insanely charming little bistro where Will and I had our rehearsal dinner (and where my parents had theirs 31 years before us!). If you’re looking for a romantic spot outside the hustle and bustle of town, head to ‘Sconset for a splurge-worthy meal in The Chanticleer’s rose garden. The chapel where we were married is just across the street!

  • Club Car

    This Nantucket classic has been given a light and bright new look and is a centrally located spot for a last-minute reservation in town. Come with friends and order a variety of small plates for the table, then stay for a rowdy evening gathered around the piano in front.

  • Cru

    One of my favorite lobster rolls on the island comes from this exquisitely decorated oyster bar on Straight Wharf. Make reservations well in advance or be prepared to wait with a glass (or two) of rosé on their outdoor patio or at the bar in the front room. It’s definitely a splurge for lunch or dinner, but the chic nautical interior and waterfront views are worth every penny.

  • Galley Beach

    If you’re willing to overlook the $25 cocktails and mediocre service in favor of the island’s best sunset, Galley Beach is a must for pre-dinner cocktails with your toes in the sand. Make dinner reservations in advance or scope out a firepit a couple hours before sunset. Call ahead on weekends to make sure it’s not closed for a wedding or rehearsal dinner.

  • Greydon House

    A newcomer to the downtown restaurant scene and one we love for a leisurely weekend brunch or group dinner. The decor is as stunning as the exterior and the cocktails served in copper pineapples have Instagram app written all over them.

  • Lola 41

    This buzzy sushi restaurant only takes same-day reservations, so call right at 4 p.m. or pay them a visit in person to secure a table or a spot at the sushi bar. It’s decidedly trendy by Nantucket standards, but the sushi is out of this world.

  • Millie's

    If you’re looking for casual Baja fare like fish tacos and lobster quesadillas, Millie’s is the place. Make it a beach day in Madaket with snacks from Millie’s Market or kid-friendly fare from the takeout window, or take an Uber out in time to enjoy the killer sunset with an infamous Madaket Mystery in hand. I may be biased as my cousins and siblings worked here for many summers, but it’s the perfect spot when you’re ready for a break from fancier dining options in town. They also have a food truck parked at Cisco Brewers!

  • Proprietors

    An eclectic spot in town that’s a favorite for dinner with girlfriends. Order a bottle of rosé and a variety of shareable plates – and don’t leave without trying the fried broccoli!

  • The Summer House

    Go for lunch downstairs at the Beachside Bistro (where we had our wedding reception!) or make dinner reservations at the main restaurant up top and stay for cocktails in the piano bar (where we had our after party!).

  • Ventuno

    Hands down the best Italian food on the island and lovely service to boot. Enjoy a cocktail in the “back bar” (outdoor patio) or the wine bar upstairs. We love the ricotta and honey crostini to start, and you can’t go wrong with any of the pastas.

Breakfast / Brunch

  • Black-Eyed Susan's

    A Nantucket institution with a wait time to match. Get here early for the best pancakes you’ll ever have. Cash only!

  • Downyflake

    The best mornings start with a donut run to Downyflake. Located near the mid-island Stop & Shop, the diner has a family-friendly retro vibe, but we usually pick up a box of cinnamon sugar donuts and enjoy them at home. Cash only!

  • Island Kitchen

    We love eating outside at Island Kitchen, which always seems to accommodate our large group. You can’t go wrong with the avocado toast, breakfast burrito, or eggs Benedict.

  • Lemon Press

    Now located on Main Street, Lemon Press is a go-to for acai bowls, avocado toast, breakfast sandwiches, and smoothies.

  • Met on Main

    My favorite brunch spot in town, both for the food and the decor. You have to get an order of buttermilk biscuits with honey-maple butter – I literally dream about them in the winter. And is it weird to say go check out the wallpaper in the bathroom? It’s my favorite.

Coffee

  • 45 Surfside

    A pretty bakery and café with ample indoor and outdoor seating. A go-to spot for grabbing an iced coffee and a croissant en route to Surfside Beach.

  • Espresso To Go

    A local favorite, Espresso To Go has a location on Old South Road and a sister location called Fast Forward on Orange Street in town. We love walking the dogs here and enjoying our coffee underneath their bright yellow umbrellas.

  • Handlebar Café

    If you’re looking for a barista who really knows his stuff, this is the place for you. The service is delightful, there’s a water bowl out front for pups, and the back garden is a hidden treasure.

  • Island Coffee

    Steps off of the Steamship Authority ferry is this tiny coffee counter on Broad Street. It’s been known to save me when I’m racing to catch an early boat, but I’ll make a detour anytime for their out-of-this-world corn muffins.

  • 'Sconset Market

    This isn’t so much a coffee shop as the only bakery and grocery store on this side of the island, but they happen to serve my favorite iced coffee on the island. My entire life I’ve insisted on sneaking out of church a few minutes early to get in line for their blueberry muffins, which are the most divine sugar-filled confections in the entire world and sell out like clockwork every weekend morning. We may or may not have placed an order for two dozen the morning of our wedding!

Takeout

  • Bartlett's Farm

    A family-run farm near Cisco Brewers with a market filled with beach picnic fare. Their legendary tomatoes pop up on menus all over the island. They also have a darling flower and produce truck on Main Street every morning!

  • Oath Pizza

    A create-your-own-pizza counter located on Straight Wharf next to the Hyline ferry dock. The line is always out the door but I swear the pizza is worth the wait! The outdoor seating on the water makes for a very affordable meal with a view.

  • Provisions

    A beloved sandwich shop on Straight Wharf famous for its Thanksgiving-inspired Turkey Terrific.

  • Something Natural

    A sandwich shop on Cliff Road with grab-and-go food for the beach or outdoor picnic tables for a casual outdoor lunch. Don’t miss their homemade chocolate chip cookies!

  • Sushi by Yoshi

    We love ordering sushi from this little spot in town and driving out to eat on the beach at Brant Point Lighthouse.

Things To See + Do

  • Brant Point Lighthouse

    The closest lighthouse to town and a great spot to catch both sunrise and sunset. Grab an ice cream cone from Juice Bar and walk down to the lighthouse to dip your toes in the water and wave to passing ferries.

  • Cisco Brewers

    A brewery, distillery, and winery with three separate bars for each. With several food trucks, live music, and puppies everywhere, it’s easy to spend the whole day.

  • Great Point Lighthouse

    Rent a Jeep with an oversand vehicle permit, stop to let air out of the tires, and make the nearly two-hour drive out to Great Point. We drove out for the sunrise and had the place to ourselves!

  • Juice Bar

    The best ice cream on Nantucket and quite possibly anywhere. The line often stretches around the block, but the smell of homemade waffle cones is always enough to keep me waiting. I’ve ordered the cookie dough for at least twenty years now and it’s never once disappointed!

  • Rent Bikes or Vespas

    Head to Nantucket Bike Shop on Broad Street and rent a bike or Vespa for the day. The island has incredible bike paths leading out of town to Surfside Beach and all the way to ‘Sconset, but it’s also fun to rent a Vespa and cruise over the cobblestones more comfortably.

  • Sailing on The Endeavor

    We love this sailboat charter so much we took some of our engagement pictures on it! Book a spot on one of the four daily departures or rent out the boat for a 90-minute private charter with family and friends. Bring your own food and beverages and say hi to Captain Jim for us!

  • sankaty lighthouse nantucket

    Sankaty Lighthouse

    At the end of Baxter Road where my family’s original home was sits our favorite lighthouse on the island. We took our engagement and wedding pictures here and had my parents recreate theirs from 31 years prior!

  • 'Sconset Bluff Walk

    An only-on-Nantucket experience, the ‘Sconset Bluff Walk is a public walking path that takes you from the village of Siasconset almost all the way out to Sankaty Lighthouse through the backyards of some of the island’s most exquisite homes. To get to the start of the walk, turn right after 21 Front Street and make a quick left.

  • Whaling Museum

    If you get stuck with a rainy day during your visit, spend an afternoon at the Whaling Museum in town to learn about the history of Nantucket. Bonus: you’ll be just across the street from an ice cream cone at Juice Bar!

Shopping

  • 28 Centre Pointe

    If I could decorate my home from just one boutique on the island, this would be it. You’ll find gorgeous furnishings, decorative items, and hostess gifts by the likes of Amanda Lindroth, Kate Spade, and Oomph – so consider this a warning that you’ll want to buy (or at least Instagram) one of everything.

  • CJ Laing

    CJ has a primary location in town and a tiny boutique out in ‘Sconset, both of which carry an assortment of preppy-meets-bohemian clothing and accessories. Think Rebecca de Ravenel bon-bons, straw tote bags, and striped maxi dresses set against grasscloth walls and white floors… yes please.

  • Flowers on Chestnut

    I worked three days a week at Flowers on Chestnut and three days a week at Ralph Lauren the summer I turned sixteen, so this flower shop always brings back fond memories of one of my favorite childhood summers. Their fresh flower assortment is unparalleled, while the gift shop upstairs carries pretty candles, coffee table books, and throw pillows.

  • In The Pink

    My cousin worked in this store for six or seven summers and I can’t walk inside without thinking of our first jobs on the island! This Lilly Pulitzer signature store is located at the bottom of Main Street and is always a colorful oasis on an overcast day.

  • Lion's Paw

    A dreamy decor spot on Main Street with beautiful artwork, home furnishings, and hostess gifts.

  • Milly & Grace

    A girly boutique just off Main Street where you’ll find clothing, accessories, home decor, and quite possibly the friendliest sales associates on the island. The owner’s sister Caroline planned our wedding – be sure to check out Milly & Grace Weddings if you’re a Nantucket bride-to-be!

  • Peter Beaton Hat Studio

    My Grandy’s signature hat is the ‘Sconset Stroller and she buys a new one every summer or two in this tiny studio attached to the owner’s home in town. If you’re willing to splurge on a stylish souvenir, pick out your hat, customize it with a wide assortment of grosgrain ribbons, and carry it out in one of their instantly recognizable black and white striped hat boxes. I also dream about the day I can dress my future children in their monogrammed swimsuits and rainboots!

  • Ralph Lauren

    One of a small handful of brand names on the island and one that feels right at home on Main Street. I always stop to admire the elaborate window displays, which are always decked out for holiday weekends.

  • Skinny Dip

    A collective concept store on Old South Wharf that features brands including ACK v. Hamps artwork, Harding Lane needlepoint accessories, and Solid & Striped swimwear.

  • Southern Tide

    This preppy Southern brand has made its way to New England and into its own storefront on Main Street. It’s a go-to of mine for dressing the men in my life, but I’ve found several cute things for myself as well!

  • Vineyard Vines

    Named after nearby Martha’s Vineyard, Vineyard Vines has a new home on Straight Wharf with preppy clothes and accessories for men, women, and children.

Where To Stay

  • 21 Broad

    A reasonably-priced hotel in a great location two blocks from the Steamship Authority and right up the street from the Juice Bar. Expect colorful decor, modern amenities, and an outdoor deck for happy hour.

  • 76 Main

    A recently renovated boutique hotel located at the top on Main Street with nautical decor and a central courtyard.

  • Airbnb

    For a unique experience, you can use Airbnb to rent a home, an apartment, or even a boat moored in the harbor!

  • Brass Lantern Inn

    A bed-and-breakfast in a 19th century building walking distance from downtown restaurants and shopping. Dog-friendly!

  • The Cottages at the Boat Basin

    A series of waterfront cottages and lofts on Old South Wharf overlooking the Nantucket boat basin and walking distance to Main Street. Dog-friendly!

  • Greydon House

    A buzzworthy new hotel and restaurant on Broad Street designed by Roman and Williams. From the window boxes on the exterior to the blue and white Portugese tiles in the shower, this is a design lover’s heaven on earth.

  • Harborview

    A collection of eleven cottages overlooking the harbor and a small private beach. Located on Washington Street and easy walking distance to Main Street.

  • Nantucket Hotel & Resort

    A year-round resort near Brant Point and Children’s Beach with an outdoor pool and antique car that will shuttle you to and from the ferry.

  • The Roberts Collection

    A collection of four inns centered around a landscaped courtyard on India Street in the heart of downtown. Expect well-appointed suites with classic decor you’ll want to recreate back home.

  • Wade Cottages

    A collection of cottages on the ‘Sconset bluff with an expansive lawn looking out over the Atlantic Ocean. Available only for week-long stays.

  • The Wauwinet

    The island’s only Relais & Châteaux property is a splurge-worthy seaside escape ten miles from the hustle and bustle of downtown. Several of the rooms and cottages boast sweeping views of Nantucket Bay, while all guests will enjoy their two private beaches and complimentary boat service to town on the Wauwinet Lady.

  • The White Elephant

    A harborfront hotel with a range of accommodations including standard rooms and suites, a new Lilly Pulitzer-designed cottage, and modern downtown lofts. The main hotel is walking distance to town and Children’s Beach, but their free shuttle will bring you to the ferry or other beaches on the island.

FAQs

  • What would you recommend for a Nantucket bachelorette weekend?

    I would try to do something lowkey the first night like ordering in takeout, food trucks at Cisco Brewers, or a dinner reservation at Millie’s and then something a little fancier like Cru on the second night. And even if your night takes you to dive bars like the Chicken Box, Slip 14, or Straight Wharf, I’d splurge on sunset cocktails at Galley Beach one night if you can score group seating on the sand. During the day, I’d head to the beach or book an activity like chartering a sailboat, doing stand-up paddle boarding with Paddle Nantucket, or taking a Go Figure barre class on the beach.

  • What would you recommend for a Nantucket honeymoon, minimoon, or anniversary celebration?

    I would recommend staying at a nice hotel in town like Greydon House or the White Elephant and renting bikes as your primary form of transportation. I would definitely make dinner reservations at Cru, Galley Beach, or Ventuno, all of which would be walking or biking distance. A sailboat ride on the Endeavor is always a special treat if you’re willing to spend more than you would at a restaurant to bring your own bottle of wine and picnic fare. And whether you decide to bike the six miles out to ‘Sconset or take an Uber, I highly recommend spending an afternoon on the ‘Sconset Bluff Walk taking in the island’s most beautiful homes before a romantic dinner at the Chanticleer.

  • What would you recommend for a family-friendly vacation?

    I defaulted to the pros here: my parents! Before they bought their house on the island, we would stay with my Grandy or rent a house for 1-2 weeks. They would always bring our car across on the ferry and do a big Costco run to fill the trunk with things like breakfast food, snacks, and toiletries that are more expensive to purchase on the island. Children’s Beach and Jetties Beach in town have very calm water that’s great for young kids, as does Sesachacha Pond out in Quidnet if you’re willing to make the drive from town. You could definitely do a 90-minute sailboat charter as a family, Millie’s is an easy pick for a kid-friendly dinner and Black-Eyed Susan’s or Island Kitchen would be good spots for a group breakfast or lunch. And ice cream cones at the Juice Bar are a must for kids of all ages, yours truly included. 😉

  • What would you recommend for a dog-friendly vacation?

    We love bringing Rory to Nantucket! Cisco Brewers is always filled with dogs but Rory prefers running around at Sankaty or at Madaket or Surfside Beach (on a leash, unless it’s the off-season). We’ve also brought Rory and my family’s dog Coach along for a sailboat ride on the Endeavor and they were obsessed!

  • What would you recommend for visiting Nantucket in the off-season?

    Definitely look up which restaurants are open depending on the time of year you’ll be visiting. Some places close in October and don’t reopen until April or May, while others remain open for off-season weekends like Christmas Stroll. It’s nice to have a car on island in the off-season if you’re willing to bring yours across on the ferry or rent one from Affordable Rentals (hint: not always affordable) or Hertz, but you can definitely get by using Uber or the Wave shuttle if need be, particularly if you’re staying in town. We love taking off-season walks on the beach (even when it means bundling up in sweaters and jackets), plus visiting in the off-season means you’ll have any of the three lighthouses to yourself!

  • If I'm planning a trip to Nantucket, is it worth it to make a day trip to Martha's Vineyard?

    I’m embarrassed to admit this, but I’ve never been to Martha’s Vineyard so I’m afraid I don’t know! I always say one of these days I’ll have to take the ferry over for a day (or explore Cape Cod for a day or two before heading to Nantucket), but it’s as if the second I have the option of being on Nantucket, I don’t want to be anywhere else. I’ll be sure to update this if I ever venture out!

  • What should I pack for a week on Nantucket?

    This obviously depends on the time of year, but my summer uniform involves a lot of striped shirts, white jeans, and Jack Rogers or espadrilles. Don’t forget a cable-knit sweater or comfy sweatshirt for chilly evenings in line at the Juice Bar (cold weather has never stood in the way of me needing to get my fix!) and a raincoat or windbreaker for gray days (and it’s likely you’ll have one or two if you’re staying for a week). For daytime you’ll want swimsuits, cover-ups, and sneakers if you’re renting bikes; for evenings you’ll probably want a dress or two depending on where you’re dining (but nothing fancy – a Lilly dress will work at even the ritziest of Nantucket restaurants). I tend to avoid heels (besides the aforementioned wedges espadrilles) on the island, particularly if I’m anywhere near the cobblestone streets in town. I’ve watched too many tourists roll their ankles on Main Street to take the risk!

  • What's the easiest way to get to Nantucket?

    Let me start by saying Nantucket can be notoriously difficult to get to and it’s best to go in with the mindset that the juice will be worth the squeeze. Your two options are to arrive by plane or by ferry. Direct flights are available from Boston, New York, and Washington, D.C. Ferry options are available from Hyannis on Hy-Line (one hour) or Steamship Authority (one hour or two hours and 15 minutes, depending on whether you want to bring your car) as well as New Bedford on Seastreak (two hours, but you’ll stop short of all the traffic on Cape Cod). Traveling from Connecticut, we typically take the Seastreak ferry from New Bedford, but if it’s the off-season or we’re bringing a car, we do Steamship Authority. When we lived in Dallas for two years, getting to Nantucket meant a flight to Boston or New York and then a connection to fly to Nantucket. Seastreak also operates a six-hour ferry from New York but personally I’d rather be in a car than on a boat for that long!

  • What's the easiest way to get around Nantucket?

    My top preference is to have a car on the island, but it’s around $400 round-trip to bring yours across and often more expensive to rent one for the weekend, so it depends on with whom we’re traveling and how long we’ll be staying. If we don’t bring our car (or have a sibling or friend’s already on the island), we rely on Uber, bikes, and the WAVE shuttle, which is clean and reliable but not always super convenient if you’re staying outside of town. If you’re staying in town, you can absolutely get by without a car – you’ll only need to rent bikes or call an Uber if you want to see ‘Sconset or dine at Millie’s in Madaket.

  • What would your 36 hour guide to Nantucket look like?

    If you only have 36 hours on the island, I would recommend staying at a hotel in town. If you can arrive on Friday evening, I would make reservations at Cru to enjoy a lobster roll and glass of rosé on the water and then walk to Juice Bar for a homemade waffle cone.

    On Saturday morning, I’d recommend renting bikes and biking the seven miles out to ‘Sconset (or taking an Uber if that sounds too rigorous) to treat yourself to iced coffee and blueberry muffins from the ‘Sconset Market. Spend an hour or two on the ‘Sconset bluff walk enjoying the beautiful homes and ocean views as you head toward Sankaty lighthouse. Once you’ve worked up an appetite for lunch, head back on Baxter Road then walk across the foot bridge to the Summer House Beachside Bistro where you can compare lobster rolls with the one you had last night.

    If you’d rather relax than get your 10,000 steps in, stop and pick up beach fare from Bartlett’s Farm before making your way to Ladies Beach, a spot with manageable waves that’s not nearly as crowded as nearby Surfside. When you’ve had your fill of sun and sand, head to Cisco Brewers for sangria or a Whale’s Tale pale ale at a picnic table near the live music.

    Saturday night is all about the sunset. If you’re willing to splurge, make dinner reservations at Galley Beach (or go there for cocktails and Ventuno in town for dinner). If you want something a little less pricey, enjoy the sunset on Madaket Beach before margaritas and tacos at Millie’s.

    On Sunday morning, have your hotel hold on to your luggage so you can enjoy your final day in town. Get in line early for breakfast at Black-Eyed Susan’s or enjoy a leisurely brunch on the back patio at Met on Main. Then spend your remaining hours doing a little shopping (28 Centre Pointe, CJ Laing, and Milly & Grace are my favorites) or picking out a hat and ribbon combo at Peter Beaton. If you have time, you could walk or bike to Brant Point lighthouse, but no one would blame you if you skipped the field trip in favor of one last Juice Bar run before your boat!

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