Nantucket: Small but Mighty. The Insider's Guide.

Nantucket may be small, but it’s mighty when it comes to things to do, see, eat, and drink. From sun-soaked beaches to world-class dining and cozy cafés, this island has something for everyone. Whether you’re strolling cobblestone streets, sipping craft cocktails with ocean views, or devouring the freshest seafood, there’s never a dull moment.

In this second installment of our Nantucket series, we’ll dive into the must-see spots and hidden gems that make this island an unforgettable escape. If you missed the first installment, you can find it here.

Cisco Beach

First, The Beaches

The protected north shore beaches-Jetties, Steps, Children’s, offer calm, shallow waters, perfect for kids or a picnic.

The south shore is where you’ll find the surf. One of the easiest south shore beaches to access is Cisco Beach, a 20-minute bike ride from town. This outing is definitely on our rinse-and-repeat schedule. The beach itself is decent, though can be narrow and washed out, but it is one of two south shore spots where you can rent a basic surfboard or take a lesson from Nantucket Island Surf School.

Bonus: a lifeguard watches for Great White sharks which do like to make the occasional appearance

There’s not much else in the way of services here- just a hot dog stand and a row of port-a-potties. But, while the beach is the destination, the stops along the way are what we’re here for. Outbound, we might grab lunch from Raw 167’s food truck or Bartlett’s Farm, or at the honor system Farm Stand on Hummock Pond Road with fruit and produce from several local growers.

But more importantly, you will again pass these spots on your way home, so you can grab your provisions for dinner, including a $9 tomato at Bartlett (honestly so good it’s worth every penny) and today’s catch from the Raw 167 Market, so fresh it’s practically still begging to be thrown back. Or, get deliciously side-tracked at Cisco Brewery and do none of the above.

Scenes from Cisco, including “shake-a-day”

Cisco Brewery: “The Happiest Place on Earth.”

Now, Walt Disney might disagree, but honestly? It checks out. What’s better than hopping on your bike after a beach day, with salt in your ears and sand between your toes, and rolling up to a spot that used to be farmland but now has live music, food trucks, craft beer, wine, and some pretty stiff cocktails? All of which might make you forget the fact that you have a shopping list for dinner, let alone what’s on it.

On the days when the line snakes all the way through bike parking and out the parking lot, and it seems the good vibes and cold brew you came for are slipping beyond your reach, it is always a joy to run into your kid’s young friends, who might casually know the bouncer and get you in by introducing you as their parents.

And even though you need a shower, are rocking zero makeup, and are literally standing in a field in your bathing suit, it still feels special—like somehow, you’ve just scored a last-minute table at The Nautilus. Except instead of wagyu and champagne, it’s beer in a plastic cup, and you’re wondering if the guy next to you is barefoot by choice or necessity.

Surfside

Second, The Beaches

Another 20-minute ride from town is Surfside Beach. Surfside is our go-to for a full day. It’s got bathrooms and a concession stand, with surprisingly good, healthy food, prepared last summer by a team of Jamaican gals who were having such a great time, we considered filling out a job application ourselves.

It’s no Mediterranean beach club, with fancy lounge beds and chic umbrellas (seriously, why can’t we have this in the U.S.?), but they do rent backpack-style beach chairs and umbrellas, which get the job done. You do have to lug them over the dunes to the beach, along with your tacos, acai bowl, and whatever else you might have dragged from the house.

Once settled, you can take in the gorgeous, wide, white-sand stretch of beach that may or may not have just seared a full layer of skin off your feet. Then you’ll read maybe two pages of your book before dozing off for a well-earned nap.

Secret Beach (Madequecham)

And, Also, The Beaches

For a better surf experience, try ACK Surf Rental at Nobadeer Beach. Located due south of Nantucket Memorial Airport, and directly in the flight path, this beach provides the added entertainment or annoyance, of jets taking off and landing every few minutes. Great surf, though.

When the Jeep needs to stretch its legs, we head to Madequecham—a hidden, uncrowded beach perfect for watching hurricane swells. No services, though, so pack a sandwich.

Sandwiches: A New England Staple

Nantucket (really, all of New England) has mastered the sandwich game while the West Coast is still holding tryouts (hot take?). In Town alone, there are so many mouth-watering options. You can choose the Breakfast BLT from Fresh Nantucket, the Washashore Burrito (ok, ok, not a sandwich) from Lemon Press, the Turkey Terrific, with stuffing and cranberry year-round, from Provisions or the tuna salad from Something Natural, a sandwich so big it might need its own zip code. Order ahead if you can—those lines are long.

Great Point: Expensive rental and our very own Jeep

Get Off-Road at Great Point

The reason to have a 4×4 on Nantucket has less to do with surf or groceries than with the opportunity to experience the thrill of driving through the sand. And there’s no better place to off-road than Great Point. Great Point is accessed beyond the Wauwinet Hotel and requires both an overland permit and reduced tire pressure (trust us).

Once you’ve had your fill of adventure, dust off, organize your hair, and stop in for a civilized cocktail on the patio at the Wauwinet.

‘Sconset bluff walk

‘Sconset & the Bluff Walk

A favorite excursion is riding the 7.5 miles to ‘Sconset, passing through the surprising savanna-like habitat known as Nantucket’s “Serengeti.” The village feels like a real-life storybook with tiny cottages dripping with roses.

After grabbing a drink from ‘Sconset Market, walk the Bluff Walk—a mile-long public footpath with manicured gardens, weathered shingle-style cottages, and sweeping views. You’ll often wonder if you’ve accidentally walked onto someone’s front lawn (you haven’t).

If you’re still feeling ambitious, continue to Sankaty Head for more stunning views and some serious erosion drama.

On your way back, stop by Claudette’s for a hearty sandwich, and check out the sundial on the footbridge en route to your ocean dip. For a fancier meal, The Chanticleer awaits—though we’ve never been, because we’re lazy and don’t travel this far for dinner.

Did We Mention the Beaches? Madaket: Sunset & Millie’s

On the western edge of the island, Madaket is a perfect sunset spot. This quiet corner of Nantucket is most famous in recent history as the home of Millie’s Restaurant and Market and is worth a visit just to secure some great Mexican food. Millie’s is named for “Madaket Millie” Jewett, a strong, self-reliant Nantucketer, who only left the island 10 times in her life, and is considered a local treasure.

When It Rains

Now you might be wondering, is every day on Nantucket a picture-perfect beach day with blue skies and sunshine? Well, sadly, no. To be a true Nantucketer, you must love this island no matter what it throws at you- wind, rain, hurricanes, fog, hail, mosquitos, nor’easters, and the occasional seagull snatching your sandwich.

Town activites

Town Can Easily Consume a Day

There are an absurd number of independent boutiques, galleries, and restaurants squeezed into an accessible, compact area. In the streets around Main, you‘ll find everything from designer boutiques where window shopping is the safest option, to charming gift and home stores, to touristy t-shirt shops.

Or you can wait in line with all the other fans to have your copy of Swan Song or The Hotel Nantucket signed by Elin Hildebrand at Mitchell’s Book Corner.

And be sure not to miss the sweet little shops along the shell-lined walkways of Old South Wharf.

While out and about in town, take a wander around the yachts and pretend you’re a billionaire in for a weekend jaunt.

Or if seafaring is more your thing, amble to the Whaling Museum, where the $25 entry fee is steep but probably worth it, and imagine yourself a rugged sailor on the open seas.

Fishing, Pickleball at Nantucket Racquet Sports

Something More Active?

If you’re looking for something a bit more active, a fishing charter might be your speed. There are many outfits, but we went with Albacore Charters—a local, father-son duo—and caught some mighty fish. While others would eat their catch, we had Pete’s Fish Tales make a Japanese-style print of ours instead.

A fishing charter is pricey and requires advance planning, but is a great way to spend a day.

Also in the active category, If you’re wondering, yes, we did find a workout—a CrossFit class at Nantucket Cycling and Fitness. It’s outdoors, which is a fun twist, and runs rain or shine, and let’s just say… we got wet. We also got a couple of decent workouts in at Nantucket Health Club.

If tennis is your thing, we can’t help you because we did not play. But we can tell you that for sure, you will need impeccable tennis whites, so pack accordingly.

We did, however, enjoy a few games of pickleball at Nantucket Racquet Sports. Out by the airport with no dress code. Enjoy it while it lasts because it certainly feels like the kind of noisy, lowbrow, accessible thing Nantucket will outlaw

Sandbar at Jetties

Happy Hour & Dinner

Now that we are all thoroughly exhausted, it’s definitely 5 o’clock somewhere. As you might have gathered, our fave spot for happy hour, hands down, is Cisco Brewery.

If we’re closer to town already, we might pop into Sandbar at Jetties, for $1 oysters with toes-in-sand, or maybe try our hand at the ever-popular game, Shake-a-Day: A high-stakes dice game where you challenge the bartender for glory (or just another round).

Creating our own happy hour

Beach Picnic

Or we might pack our own party and have a game of wiffleball at Steps Beach while waiting for the sun to set. There’s always our very own patio, where we might serve up Cisco’s Wandering Haze IPA or Cranberry vodka, acquired last time we were at the Brewery.

Happy hour rolls into dinner. If taken on the patio, dinner will involve the catch of the day from Raw 167 Market, hopefully, turned into ceviche if Scotty is in town, and whatever is in season at Bartlett Farm.

We limit our eating out because the prices can feel like highway robbery and getting reservations, especially for a group, is like an Olympic sport. When it’s just the two of us, which is not often, we usually roll the dice and try to sit at the bar.

The Nautilus is probably the hottest dinner ticket in town. It’s tiny, so getting a ressie is like winning the lottery, but it is worth the effort. Proprietors has the ambiance and Straight Wharf is also a solid move.

If you have a crowd in town, and you’re sick of cooking, the newly re-imagined Brotherhood of Thieves, (with the best restaurant name ever) has several casual spaces and decent food. Or grab one of the killer to-go boxes from Millies at the Rotary and chow down at home on the patio. Or order a fully-cooked clambake from Sayle’s Seafood and take it out to Brandt Point.

Many other dinner options in the rated lists below.

Juice Bar

Did Someone Say Dessert?

Two things to know about The Juice Bar. First, the line is never too long. And the second, you are never too full for ice cream. What could be better than homemade Crantucket ice cream on a waffle cone? Just don’t wait too long, as the line closes promptly at 10:30 pm in summer. And yes, we have cheated on the Juice Bar from time to time but it’s just not the same.

Chicken Box, then and now (Sumbuck playing)

Nightlife

By this point, you are probably ready to rest your weary head, but the night is young! In the words of Billy Joel, “It’s 9 o’clock on a Saturday, and the regular crown shuffles in” for the sing-along at The Club Car. At this vintage railcar-turned-bar, where no one can sing but everyone tries, the magic happens when the entire room belts out “Sweet Caroline,” raising their glasses like lifelong friends at a reunion.

Or for a legit music scene, check out the line-up at the Chicken Box, where we were fortunate to see Sumbuck (Caamp) play in a tiny venue. Or Gaslight, which hosts some great DJs.

It is always sad to say goodbye, but the sting of leaving Nantucket is softened by the idea that we might return for Stroll. And, hey, maybe Daffy too!

To get the full backstory of our Nantucket stay—click here.

🐳🐳🐳🐳🐳 ACK-tastic

Albacore Charters – For a fishing excursion
Bartlett’s Farm – For produce and lunch
Brandt Point Light – To greet you at the harbor
Cisco Brewery – For all the vibes, live music, food trucks, and bevies
Chicken Box – For legit live music
Claudette’s – For a great sandwich in ‘Sconset, best eaten fresh
The Club Car – For the 9pm sing-along
Fresh Nantucket – For the breakfast sandwich
Great Point – For the freedom to drive through the dunes
Handlebar Cafe – For the cappuccino, oat, extra hot
Hummock Pond Road Farm Stand – For local organic produce on the honor system
Jetties Beach – For the calm waters, close to town
Juice Bar – For the experience of waiting an hour for an ice cream cone
Lemon Press – For healthy, creative wraps and bowls
Madequecham – For a blissfully quiet beach
Millie’s – For great Mexican and sandwiches in Madaket
Millie’s at the Rotary – For the takeout boxes that save you from cooking yet another meal
Mitchell’s Book Corner – For book signings
NanTaco – For friendly service and great tacos
The Nautilus – For the best meal on-island, if you can get a res
Nantucket Cycling and Fitness – For outdoor CrossFit
Nantucket Racquet Sports – For pickleball under the lights
Pete’s Fish Tales – For a Gyotaku print of the fish you caught
Proprietors – For good food and ambiance
Raw 167 Food Truck and Market – For the freshest fish
Sankaty Head Lighthouse – For a postcard-worthy photo
‘Sconset – For the rose-covered cottages
‘Sconset Bluff Walk – For the views of the ocean and the homes
Slip 14 – For a friendly food & drink spot
Steps Beach – For late afternoon wiffleball
Stop ‘n Shop Mid-Island – For all your staples
Surfside Beach – For the amenities
Town – For all the shopping
Walter’s Deli – For the best lobstah roll
Wauwinet Hotel – For the drink on the porch
Whaling Museum – For the scrimshaw
Young’s Bike Shop – For the best bike rentals

🐳🐳🐳🐳 We’d go b-ACK

ACK Surf Rental – For boards at Nobadeer
Cisco Beach – For access to Cisco Brewery on your ride home
B-ACK Yard BBQ – For a very casual and surprisingly good BBQ joint
Bar Yoshi – For sushi on a shell-lined walkway
Black-Eyed Susan’s – For brunch
Born & Bread – For excellent bread, if you can be bothered to wait in line
Brotherhood of Thieves – For decent food in a low-key setting
Flowers on Chestnut – For the most stunning bouquets at eye-watering prices
Gaslight – For the DJs
Lola 41 – For the sushi
Madaket Beach – For Millie’s and sunset
Nantucket Health Club – For general fitness
Or, the Whale – For the massive pork BBQ and the back patio
Provisions – For the Turkey Terrific sandwich
Sandbar at Jetties – For sunset and toe-in-sand cocktails
‘Sconset Market – For refreshments pre/post Bluff Walk
Straight Wharf – For the dining room
Ventuno – For Italian

🐳🐳🐳 ACK-ceptable

Company of the Cauldron – For old-school cozy vibes
Cru – For a great setting and good food, at a price
Galley Beach Restaurant – For a great setting and good food, at a price
Nantucket Island Surf School – For mediocre board rentals
Nobadeer Beach – For good surf, in the flight path
Nantucket Meat and Fish Market – For convenience
Sayle’s Seafood Market – For the clambake
Something Natural – For an overly large sandwich
Wicked Island Bakery – For a woefully short supply of morning buns

🐳 ACK-ward

Cliffside Beach Club – For non-parents
Stop ‘n Shop Town – For emergencies only