A Nantucket Bucket List for Families

The best food and the best beaches on New England’s best family getaway isle.

By Kendall Headley


The requisites of living in the real world can quickly catch up with us. Our education and jobs — even the mundane acts of sitting in highway traffic or the repetitive trip to the same grocery store.




When you need an escape from the trials of your real world, this place provides an oasis: The island of Nantucket.

Nantucket, the 14-mile-long island off the coast of Massachusetts, brags a beautiful variety of beaches, a lively downtown, and delicate coastal architecture that serves for the perfect morning walk. An hour-long ferry away from the mainland, with its unique lack of traffic lights and sprawling stretches of undeveloped coast, Nantucket creates a calm, ocean-surrounded escape — both physically and mentally — from the stress of life. And yes, the words of Elin Hildebrand’s acclaimed Nantucket-based novels practically fly off of the page.

While small, Nantucket has no shortage of land to cover. Home to ten major public beaches (and many minor but just as worthy), more than 60 restaurants, and six constituent neighborhoods, it can be difficult to choose what spots to hit during limited vacation time.

After several trips, here is a “bucket list” of nonnegotiables on this incredible isle.


The Perfect Morning in Nantucket

Upon waking, we notice quickly that one thing follows us from the real world: our caffeine addictions. Thankfully, Nantucket’s coffee shops won’t let you down. Head to Born & Bread in town for a delicious cup, along with hearty sourdough breakfast sandwiches and hand-crafted bakery items. We simply couldn’t resist buying not only one, but two of their blueberry muffins on our recent trip, along with a loaf of their homemade bread.

A morning walk is necessary for an island vacation, and the Sconset Bluff Walk is perfect every step of the way. Walk on a small path through the backyards of beautiful shingled homes with manicured gardens of bright hydrangeas. To the left, you experience luxurious yet cozy homes, and to the right, you see the wide expanse of ocean. The path ends at the Sankaty Head Lighthouse, a nautical photo-op and a sweeping view of the rest of the island. Walk back to downtown Sconset on Baxter Road for the front view of the magnificent homes.

Best Beaches in Nantucket

The beaches you will enjoy largely depend on the vibe you are looking for: If you prefer laying under the sun, hearing only the slight wash of small waves, and only wading in on occasion to cool off, Steps Beach is your dream destination. A mile out from town on the bayside, Steps boasts a clear view of the coast, dotted with shingled houses and green hills, and tranquil waters perfect for a quick dip. If you go in the evening, the sunset experience is unmatched.

If you’re the adventure type, tending to spend hours in the water jumping waves, surfing, and boogie boarding, then head to Nobadeer. Nobadeer is one of Nantucket’s drive-on beaches, which allow permitted cars to drive on and park near the water. A beach permit is easy to acquire — This beach is no ghost town. Young adults line up their Jeep Wranglers every day to grill, throw a football, or entertain themselves with the heavy surf. Here, music on speakers and lively energy exist late into the evening.

Favorite Places to Eat in Nantucket

The food scene, largely dominated by seafood dishes, is unbeatable. For an easier dinner, park and order at the 167 Raw food truck. 167 Raw, accompanied by a small fish shop, lists a short menu including the seafood essentials. My family has ordered every item on the menu, and never have we left disappointed. Our favorites are the cold lobster roll — tossed with just the right amount of citrus-noted mayonnaise and never slighted with the lobster meat — and the ahi poke tuna — marinated with a sweet soy sauce and served with salty homemade tortilla chips. There is a small area with picnic tables outside of the truck to enjoy your order but to really elevate the meal, head down the street to Cisco Beach with a picnic blanket to watch a dreamy sunset.

If your family is anything like mine, it can be difficult to agree on a sit-down place, but we’ve arrived at two favorites. Bar Yoshi is a phenomenal sushi and Japanese restaurant downtown. The indoor space is filled with natural light, but the outdoor seating on a quaint, seashell-paved street is no less deserving. The sushi is fresh and flavorful, and the menu provides many other options including udon and juicy dumplings. Make sure to look at reservations months beforehand — but if you’re playing it by ear, their outside tables are reserved for walk-ins.

If sushi is not your thing, head to Millie’s, a strictly walk-in joint. Americanized Mexican at its finest, Millie’s serves quesadillas, salads, and tacos, most featuring local seafood. At the tip of Madaket, Millie’s also flaunts the yearned-after-sunset view.

A summer day on Nantucket cannot be ended without dessert — and The Juice Bar will satisfy all your wildest cravings. This small ice cream shop churns up homemade, creative flavors, ranging from dirty grasshopper (chocolate mint base with Oreos) to black raspberry. These employees deserve a raise: They make in-house waffle cones and cups, which are still warm when served with your ice cream. Don’t be intimidated by the line; it moves quickly and the end product is absolutely worth the wait.

If you favor baked goods, stop at Something Natural earlier in the day, before the 6 p.m. close, and pick up a bag of chocolate chip cookies. These cookies are thin and chewy, with crispy edges and just the right amount of sweet chocolate bits — oh, and if the Nantucket sun leaves you with a late-night sugar craving, the Stop n’ Shop mid-island sells Something Natural chocolate chip cookie dough, so pick up a sleeve if you want them freshly baked.

Where to Stay in Nantucket

We’ve covered beaches, downtown areas, and restaurants — and if you want easy access to all three, neighborhoods west of town are nothing but perfect. Just down Cliff Road, there are smatterings of rentals, varying in size and price. It’s a safe, direct walk into town for late-night ice cream, less than two miles away from a variety of beaches (including Steps, my aforementioned favorite), and — the best part — you can reach most of my listed destinations while avoiding mid-island traffic. But, if you want complete serenity, consider Tom Nevers. Within the isolated neighborhood, quiet streets separate large yards, and just about all two-story houses can view the water. The beach is only accessible through a few entrances, almost solely used by neighbors — lending to near vacancy.

If you plan to stay for at least a week, renting a house is ideal; you get the peace and quiet of private living quarters without giving up the convenient locations. Websites for booking are plentiful, with options listed on Airbnb, Great Point Properties, Fisher Real Estate, The Copley Group, and We Need a Vacation. However, if a weekend trip is in the works, plenty of hotels offer similar opportunities. In town, Faraway Hotel combines quirky design with modern minimalism and includes the Sister Ship, a downstairs bar with a beautiful outdoor garden. The Wauwinet Hotel, on the contrary, is located in Wauwinet, a remote stretch of island between the ocean and Head of the Harbor, a still body. The Wauwinet provides shuttles to and from the ferry, along with private beaches, and tennis courts. Equipped with a tasteful restaurant, you won’t be missing a thing.

How to Get to Nantucket

Nantucket is 30 miles off of the coast of Hyannis, a small town on the Cape. This ferry will be the quickest ride — on the high-speed ferries from Hy-Line and Steamship Authority, you will be on-island within the hour. Ferries also depart from New Bedford, MA, and Harwich Port, MA. These will take between an hour and a half to two hours. Steamship Authority also provides car ferries, but stay on your toes — getting these reservations is like buying Taylor Swift’s concert tickets, even months before your trip. Flying is an option, although Nantucket only holds one airport, so it’s highly expensive.

When to Go to Nantucket

Summer is their flourishing season; temperatures rest at a comfortable 75 and sunny, yet cooler at night, and all shops re-open in a lively fashion. However, the holiday season is not to be discredited. Near Thanksgiving, Christmas trees get set up along downtown streets, shops host major sales, and restaurants bring in specials for the incoming crowd. Not to mention, the Annual Cold Turkey Plunge is a great way to give, funding the Weezie Library for Children, while knocking a polar plunge off your bucket list. The Annual Christmas Stroll held on the first full weekend of December brings holiday cheer to a maximum: Main street in town is closed off to drivers, while events including caroling, ugly sweater competitions, and cookie decorating commence. But don’t forget to bring a jacket — those northern winter chills are only intensified while surrounded by the ocean.

It’s safe to say any season in Nantucket will suffice for a trip filled with magical memories and relaxation. Whether your dream vacation is seven days of uninterrupted beach time or your itinerary is filled to the minute, Nantucket will leave you fulfilled, and needing to go “bACK.”


Kendall Headley  – August 2023

ROAM Contributor   

Kendall is a D.C. native who loves writing, music, and exploring new places. In her spare time, she’s an avid documentary watcher and Boggle expert who can’t stay away from a good dessert recipe.
© ROAM Family Travel 2023 – All rights reserved


ROAM with us! Read more REAL family adventures


Don’t miss a single trip! Enter your email address in the box below to subscribe to ROAM and receive notifications of new posts by email. Check your inbox for an email to confirm your subscription, click the link and you’re ready to ROAM!