How to Spend the Perfect Long Weekend on Nantucket
The can’t-miss spots, shops, and stays to add to your island bucket list.
ByKara Neff
Published On
Photo by Kara Neff
Welcome to Like a Local, our travel series where writers share how to spend an ideal long weekend in their favorite hometowns. This time, Kara shares her favorite spots on Nantucket.
Living on Nantucket year-round offers me a fortunate perspective on the reawakening of summer each year, and a newfound appreciation for the warmth and sunshine that the season brings. The nine-or-so months in between Labor Day and Memorial Day are beautiful, but quiet, slow-paced, and oftentimes, grey. But as winter begins to thaw and the temperatures start to rise, the island begins to show off—sweeping dunes that dance in the sunlight, cobblestone streets teeming with renewed summer energy, and a seemingly endless bucket list.
Navigating the must-sees can admittedly feel overwhelming. Luckily, this local is happy to share the best things to see and do in one full weekend on this beloved island.
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Where to stay
A quintessential Nantucket experience requires knowing where to stay. If a hotel is your preferred vibe, The Faraway is cute and spunky in all the right ways. Plus, it’s centrally located in town, making it incredibly accessible to dining and sightseeing. The restaurant within, Sister Ship, boasts a stellar menu and cocktail list—not to mention a lively garden experience to enjoy said menu items.
Similarly, The Beachside Hotel is just a stone’s throw from the ocean, has a pool, and has been furnished with the just-right levels of modern beach vibes. (The Schoolhouse furnishings are not to be missed.)
But if you want to spread out, a Nantucket home rental is the perfect way to feel like a true local. Renting in town offers the same accessibility as a chic hotel stay, and venturing out further, like a beach cottage in Sconset, can be a truly immersive experience.
Sconset—a personal favorite—is far removed from the worn and beaten path, but it offers a quiet quaintness that’s unlike anywhere else on the island. Peppered with charming, picturesque homes, this old fishing village hosts just what you need—a market, a post office, a sandwich shop, beach access—and not much more. If getting away is part of your getaway plans, Sconset may be the perfect place for you.
Madaket, on the opposite end of the island, is another destination to consider for your stay. Not altogether different from Sconset in that it’s far from town, and boasts even fewer amenities (aside from Millie’s, the premier place to park yourself to enjoy a margarita and an island sunset), it is tranquil and isolated in all the right ways.
Where to Eat & Drink
The Nantucket food scene is next-level, with menus that hold their own—if not one-up—some of the best dining hotspots in the country. Here’s what to try:
Breakfast
- Born & Bread | A sourdough experience—grab your own organic loaf for home, or try any sandwich or baked good on the menu. You won’t regret it.
- Lemon Press | The go-to spot downtown for coffee, organic juices, and a Persian-inspired menu that’s good-for-you and just plain good.
- Handlebar Cafe | A little ways from Main Street, but not too far to people-watch—sit next to their iconic blue truck outside with an iced oat milk latte and a pastry.
Lunch
- The Wauwinet | TOPPER’S overlooks Polpis Harbor, making a lunchtime meal here as much about the view as it is about Chef Kyle Zachary’s menu.
- Bar Yoshi | Perfectly situated on the island’s historic Old South Wharf, Bar Yoshi features an eclectic mix of sushi, ceviche, noodles, dumplings and more.
- Straight Wharf Fish | An immersive design and dining experience, Straight Wharf Fish is a perfect mix of locally caught dishes with a view you don’t want to miss.
- Cru | Perched at the end of the Straight Wharf, right atop the water, Cru offers up unparalleled views and a menu to match its vibe—which can sometimes lean Ibiza-ish, so tread lightly if that’s not your thing.
Dinner
- Nautilus | One of the best dinner menus on the island, if you can get a table. (Pro tip: the reservation window typically opens 7 days in advance of your desired booking. Set a calendar reminder and call exactly one week before you plan on dining to try and secure a reservation. Though not a guarantee, it may just get you a table.) And, in the event you do land a table, make sure you order the Blue Crab Fried Rice—it’s not to be missed.
- Via Mare | Matching small plates and incredible cocktails, Via Mare meets classic Nantucket with some modern flair.
- Proprietors | 9 India Street is the place to be for fresh, stunning and contemporary plates.
Late Night
- Gaslight | Live music or karaoke will carry you late into the night at this downtown venue.
- Chicken Box | Make a late night even later with a visit to an iconic Nantucket hotspot. This no-frills bar is open until 1am and, more often than not, features live music most summer nights.
What to do
At approximately 48 square miles, Nantucket is objectively small—but with a seemingly endless array of things and experiences to try. And while dining certainly tops the list, here are a few additional things to try during your stay:
- Rent a bike and ride out to Sconset, or take the bike path towards the south shore and visit 167 Raw for a lobster roll and a beer
- After the beach, hit Cisco Brewers for a cold one and, more likely than not, some live music
- Grab a coffee and shop downtown, visiting local spots like Wheat, or fashion staples like Veronica Beard, Staud, and the new Dôen store on Main Street. Check out Bodega for some home goods and Schoolhouse furniture.
- Walk the wharf to watch the boats come in and out
- Grab a book from Nantucket Bookworks and hit the beach
- Visit the iconic Steps Beach and look for shells
- Try a PainKiller at the Sandbar at Jetties Beach
Stock up on fresh, locally grown produce at The Sustainable Nantucket Farm Stand on Hummock Pond Rd.