New England’s toniest island may be tiny at just 14 miles long, but it certainly punches above its weight, thanks to glorious public beaches, sophisticated dining and shopping, and endless amounts of charm and history. Grab your chic coastal wear, pop your collar, and bookmark this hit list of Nantucket’s best to ensure your next trip to the ACK is consummate coastal chic.

What to Eat

Nantucket has a strong culinary scene — so strong, you may be tempted to double up meals to squeeze in all the top spots. Breakfast alone comes with myriad choices: Cue up with locals at Born & Bread for coffee and creative pastries (the cruffins are worth every calorie) or Black Eyed Susan’s for what many consider to be the world’s best blueberry pancakes. For more a.m. sweetness, don’t miss the morning buns at Wicked Island Bakery.

Lunch, meanwhile, is on-the-go and in the sand. For a picnic-worthy gourmet sandwich, stop by Provisions (the Turkey Terrific is legend) or Something Natural (don’t forget an oatmeal raisin cookie). If a lobster roll is on your list — and it should be — head to 167 Raw for the island’s best, and order a side of fried oysters for the table. If a reservation-only spot is more your speed, head to Cru for raw bar and rosé with views of Old North Wharf. Or keep it casual by the sea and grab a pastel Adirondack chair at Jettie’s Sandbar. It doesn’t get any better than a Jetty Burger and a Toby’s Punch.

Dinner is done-up so don your best and expect a scene (and never, ever forget to make reservations). Nautilus is a must for old-school vibes and seafood-centric small plates, especially the blue crab fried rice. For an outdoor affair, book a garden table at Chanticleer or head to Topper’s and enjoy a pre-dinner sunset drink on the lawn. The Pearl puts an international spin on local seafood with dishes like wok-fried lobster and swordfish Katsu. And dessert is always and forever the Juice Bar. Don’t let the name fool you: This beloved spot’s homemade ice cream is quite literally addictive. (Pro tip: Always order the flavor of the day.)

Where to Shop

There’s a very specific aesthetic on Nantucket­ — and, no, it’s not all paisley prints and pastels (though you’ll see plenty of that here as well). Luckily, you’ll find the island’s best and most representative boutiques within walking distance of your Exclusive Resorts residence. To familiarize yourself with the prevailing look, start at a local mainstay, such as Serenella (for boho chic cover-ups and polished evening silhouettes) or Milly and Grace (for classic blue-and-white ensembles, one-of-a-kind jewelry, and skincare splurges). The Skinny Dip, on Old South Wharf, sells a mix of men’s, women’s, and children’s clothes from independent contemporary brands, while Olivela’s highly curated selection of luxury brands presents like the Nantucket Edit of Bergdorf Goodman.

Once you’re properly attired, scoop up a quality souvenir at the Whaling Museum gift shop (archival photos and maps make excellent keepsakes) or Nantucket Looms (for the ultimate cottage-core and nautical décor).

What to Do

Nantucket is best experienced on two wheels — and there almost nowhere on the island that isn’t bike-friendly. Swing by Young’s to mount up; the cycle shop rents by the hour or the day. From there, your first stop is only a few minutes away at Brant Point Lighthouse, a site that predates the American Revolution (its current station was built in 1901). Surrounded by tall grass, it sits on the farthest point of Brant Beach, a beach bum’s paradise for its views of the yachts and sailboats entering and exiting the harbor.

No matter which direction you choose next is sure to land you at a beach. Though you’d be hard-pressed to find a bad stretch of sand around here, we recommend Cisco Beach (a cool spot for surfing), Madaket Beach (whose southwest positioning affords great sunset views), or Children’s Beach (you guessed it, best for families because of its calm waters and playground). Should you chose to make a day of it, head to Cisco Beach and, on the way there, stop at Bartlett’s Farm for snacks and a glimpse of the always-entertaining hen house. On your return, visit Cisco Brewers for beer, live music, and food trucks.

Back in the center of town, incorporate some culture into your day with a tour of the Whaling Museum — its skeleton of a 46-foot male sperm whale is always a crowd pleaser — followed by a walk down one of the island’s most quintessential streets: Old North Wharf. Lined with wood-shingle homes fronted by white picket fences and blue hydrangea, the pedestrian street is a postcard-worthy encapsulation of Nantucket and all its inimitable New England charm.