Being an island, you’d expect Nantucket to have excellent seafood options—and it does. But spend a few days walking around its quaint cobblestone streets, and you’ll find so much more than that. From fine dining to relaxed breweries, the Gray Lady is a fun place to eat your way around. Here’s where to go, no matter what you’re in the mood for.

For…A Special Occasion
Located in the stately Wauwinet hotel on the northern end of the island, Topper’s (pictured above) is a prime spot for a birthday or anniversary. The six-course tasting menu includes creative dishes like foie gras presented with cocoa and preserved cherries, and butter poached North Atlantic Lobster served with pickled coconut. Vegetarians are well catered to with their own tasting menu, which features elevated meat-free dishes like roasted cauliflower made with golden raisins and curry sauce. For a more casual, but no less memorable experience, try the deck menu (think: raw oysters harvested 300 yards away, clam chowder and lobster rolls), served on a heated terrace overlooking Nantucket Bay, with amazing sunset views. wauwinet.com

For….A Picnic Lunch
On the way to the beach, stop by Something Natural, which just opened an outpost in Greenwich, CT. Their most popular choice is the turkey and cheese served on Portuguese bread, with the Avocado, Cheddar and Chutney, and Sheila’s Favorite (a classic veggie sandwich) coming in closely behind. While they’re known for their freshly-baked bread, regulars also love their salads, cookies and organic bottled juice—all made in-house.

For…Casual Chic Ambience
Dune is a fabulous date night spot, with a quartzite bar, elegant dining rooms and impeccable service. The menu consists of dishes made with locally-sourced ingredients, like its roasted beet salad with whipped goat cheese.

Nantucker Juice Bar Cones
Cones from The Juice Bar

For…An Amazing Scoop of Ice Cream
The line outside The Juice Bar is a clear indication that they’re doing something right. And that something is making rich, homemade ice cream. Purists will appreciate basic choices like vanilla, chocolate and coffee, while those who enjoy something a bit different will love the Crantucket, Grapenut, and The Carl (chocolate ice cream with marshmallows and chocolate chips) varieties. 508-228-5799

Nantucket Cocktails
Al fresco cocktails at Cisco Brewers

For…A Local Brew and Much More
Cisco Brewers is a great place to sample local beers, but cocktail and wine lovers will also find plenty to love here. In the distillery, creative cocktails are made using house-infused vodkas; try the Kale Force One, with gin, ginger puree, cucumber and kale juice. Sangria is served on the rocks or frozen in the winery—the raspberry frose with estate grown mint has been a fast favorite. Any drink you choose can be sipped in the beer garden, where live music plays daily during the season. Sample the food truck offerings, from  swordfish sliders to steamed pork and veggie dumplings. And don’t miss the raw bar truck from 167 Raw (then visit their fish market if you’re eating in).

For…Fabulous Seafood
Eat in the grill or dining rooms at Straight Wharf—either way, you’ll enjoy their fresher-than-fresh fish dishes that change daily. Always on the menu? Their cult-favorite smoked bluefish pâté. Other popular picks are the taquitos of the day, the handmade pastas and the Nantucket oysters, served with spicy tomato and horseradish granita.

For….Farmer’s Market Fresh Produce
Cooking at home? Stock up on produce from Bartlett’s Farm, which has 40 greenhouses filled with organic greens, hothouse tomatoes, flowering plants and fragrant herbs (worth purchasing just for the fresh scent they’ll leave in your kitchen). On your way out, pick up the goat cheese spread with pesto and sundried tomatoes for an appetizer. 

For….A Happening Raw Bar
From caviar (served traditionally with crème fraiche and toasted brioche) to the daily changing menu of oysters, seafood fanatics won’t leave Cru Oyster Bar disappointed. Sit at the lively bar to enjoy the atmosphere.

For….Cocktails with a View
Galley Beach has amazing sunsets, which are only enhanced by their top-notch cocktails. Try the Mule Time, made with fresh lime, ginger beer and thyme, for a new take on a classic. The lounge and dinner menus have plenty of refined, but filling dishes like escargot, lobster frites, sweetbreads and cassoulet.

For…Top-Notch Steaks
While Ships Inn is  known for its seafood like many restaurants on island, regulars also love their perfectly cooked steaks, particularly the dry aged sirloin steak au poivre. Vegetarians will appreciate the vegetarian risotto, a satisfying entrée made with mushrooms, leeks and white truffle butter.

For…A Romantic Date Night
Get guaranteed ambiance by booking a table in the patio garden of American Seasons. These reservations fill up fast, and with good reason. The candlelight and full awning create an intimate vibe perfectly set up for quiet conversation.

Nantucket Kebabs
Kebabs from Nantucket Meat & Fish Market

For…Grilling Out
You don’t have to eat out to eat well in Nantucket. Pick up the highest quality meats, fish, prepared foods, sushi, groceries and more at the Nantucket Meat & Fish Market. Popular choices include the house steak tips, shrimp cocktail, lemon-pepper shrimp skewers, bacon cheddar burgers and kobe beef.

 

WHERE TO STAY

Nantucket White Elephant Hotel

The waterfront White Elephant hotel has been an island icon for decades, and is the perfect base from which to explore Nantucket. You’ll find light-filled rooms and suites in the main building, while the one-bedroom garden cottages are ideal for families or anyone needed a little more space or privacy. Brant Point Grill, located next to the lobby with views of Nantucket Bay, is an easy choice for a light seafood lunch; the menu is particularly heavy on tasty lobster choices, from lobster rolls to sliders. After a day of sightseeing, unwind with a trip to the spa and get your skin summer-ready with the signature detoxifying body massage, which comes with an algae wrap. Visitors will also enjoy luxury touches like complimentary access to the hotel’s fleet of BMWs (helpful when venturing to farther flung destinations like Cisco Brewery or Topper’s). The hotel brand recently launched the White Elephant Village, just steps from Children’s Beach (one of the more popular, family-friendly seaside spots). Kids staying at this resort will enjoy the poolside ice cream cart, and parents will appreciate the convenience of everything from cribs and diapers being available in rooms. From $195/night

How to Get There
Fly Tradewind Aviation directly from Westchester County Airport (HPN)
to Nantucket Memorial Aiport (ACK). This seasonal shuttle runs from April through December and flight time is a little under an hour. Because it flies out of a private terminal, you’ll relax in the comfortable Tradewind lounge instead of fighting through security.