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Lahaina, with its many Victorian flourishes, may look picturesque today, but the port town teemed with sailors, gamblers, and prostitutes in the 19th century. The Pioneer Inn changed all that when it opened for business in 1901, foreshadowing the tourist industry that would ultimately replace whaling, sugar, and pineapples. Step through the swinging doors of this vintage bar, which now bizarrely anchors the courtyard of a Best Western, and you’ll be transported back in time. Oars, harpoons, and a ship’s figurehead still adorn the space, looking down on platters of coconut shrimp, Parmesan-crusted fish over coconut rice, and margaritas made with POG (a mix of passion fruit, orange, and guava juices). Come during happy hour, which runs daily from 3 p.m. to 6 p.m., for discounted beers and cocktails.

With its thatched roof, bamboo bar, and surfboard decor, this beloved watering hole—often voted Maui’s best bar by locals—checks all the tiki boxes. Head here for live music, lanai seating, and late-night dancing, plus fun and fruity rum cocktails like mai tais, zombies, daiquiris, and piña coladas. Beyond its drinks, South Shore Tiki Lounge was recognized by the state of Hawaii as an outstanding business for its regular fund-raising efforts, which benefit local organizations like the Keiki Cupboard, Hawaii Wildlife Fund, Maui Humane Society, and Hawaii Animal Rescue Foundation. All that to say, you can feel good coming here to wash down a massive chili-cheese hot dog with a lychee-watermelon martini.

Maui’s quiet town of Wailuku is home to some of the world’s most artful doughnuts. The owner of Donut Dynamite!, who goes by her nom de cuisine “Madame Donut,” started the business as a food truck. In 2016, she opened this brick-and-mortar location after she won the “Backyard Barbecue” episode of the Cooking Channel’s Sugar Showdown. Trained at the Culinary Institute of America, she brings a high-concept approach to her signature sweets, with standout flavors including bacon-maple, cheesy hammy, and a lush purple number featuring Molokai sweet potato and poi (a Native Hawaiian staple made from taro roots). Don’t miss the legendary Cinnamon Toasty Crunchy, topped with finely diced croutons made in-house, and be sure to get to the shop early—it opens at 6 a.m. and often starts running low on doughnuts by 9 a.m.

When tragedy strikes—like the Paris terrorist attacks or the Parkland mass shooting—Nalu’s South Shore Grill creates mile-long leis from local ti leaves for those affected. Representatives then present the leis to the victims personally, while offering chants for healing. Oftentimes, the restaurant also creates the leis to celebrate accomplishments, like the return of the Hawaiian canoe Hōkūleʻa after its three-year, round-the-world voyage. Aside from being a beacon of humanitarian light, Nalu’s is a favorite for local dishes like poke bowls, island-style beef short ribs, and loco moco (a ground beef patty served over brown rice and topped with eggs, homemade gravy, and black lava salt). If you want to give back, order the roasted beet and goat cheese salad and 50 percent of the purchase price will go to charity.

As its name suggests, this strip mall gem near Kahului Airport celebrates all things poi, a Polynesian staple made by steaming and mashing the cooked stem of a kalo (taro) plant. Come here for takeout or be prepared to wait a bit—the rib-sticking fare is quite popular with locals. Must-try dishes include ramen garnished with green onions, kimchi fried rice, and the lau lau plate featuring pork wrapped in taro leaves and slow steamed to perfection. Most menu items come with poi, but you can also opt to try it in a poke bowl or on its own as a side dish. The setting here may be modest, but nothing beats it for an authentic Hawaiian meal.

Belly up to this Wailea bar, which dazzles with a display of blue-glass Japanese fishing floats, for Hawaii’s best mai tai. Here, chef Peter Merriman, a pioneer of Hawaii Regional Cuisine, brings his genius to the classic cocktail, adding a thick head of honey-lilikoi (passion fruit) foam. Be sure to also score a table for later, as Monkeypod Kitchen does double duty as one of Maui’s top restaurants. Menu standouts include such seasonal dishes as kiawe-roasted squash ravioli, coconut-corn chowder, Hamakua wild mushroom pizza drizzled with truffle oil, and bulgogi pork tacos with Asian pear and house-made kimchi.

Expect the unexpected at Ka‘ana Kitchen, set within the funky yet sophisticated Andaz Maui. Here, executive chef Isaac Bancaco draws from the best of the island’s bounty, using local ingredients in a mix of Filipino, Chinese, Japanese, French, and Native Hawaiian cuisine. Think breadfruit hush puppies, Kona clams with savory malasadas (Portuguese doughnuts), and ahi tataki with burrata and lilikoi (passion fruit), enhanced only by the restaurant’s sweeping coastal views. You don’t need to change out of casualwear to dine here, but Bancaco has a knack for turning meals into events, inspiring diners to dress up a little.

Hilo-born Sheldon Simeon realized the appeal of his soulful, heritage-based cooking as a finalist on season 10 of Top Chef. Once back in Hawaii, he opened the upscale Lineage in Wailea, where he’s earned a loyal fan base for dishes like kimchi dip, fried turkey tail adobo, and squid luau with creamed taro leaf. Cocktails here are equally creative, ranging from a mai tai made with banana milk punch, Earl Grey tea, raisins, and coconut to a cucumber vodka number garnished with huli huli chicken skin. Whatever you order, be sure to pair it with the chili pepper water, a condiment and digestive aid that’s served in a take-home flask.

At this stunning restaurant in the Grand Wailea Maui, Lahaina-born chef Alvin Savella wows diners with bright flavors and striking plating. Start with appetizers like Cantonese barbecue-style char siu pork belly, squid ink bao, and ulu (breadfruit) risotto with nasturtiums, then move on to impressive mains like lobster ramen in red miso–coconut broth and free-range huli huli chicken with garlic fried rice and charred pineapple relish. Set in a lagoon, the round, thatched-roof restaurant—named for Hawaii’s state fish, the humuhumunukunukuapuaa—offers spectacular sunset views, so plan your dinner accordingly.

Founded in 2015 by three childhood friends from Georgia, Down the Hatch brings a Southern twist to the aloha spirit. The classic watering hole serves shrimp po’boys, chicken and waffles, and Mexican-inspired fare like seared ahi tacos, but the real draw is the cocktails, which range from tiki favorites and Moscow Mules to craft libations like the Snake Oil with gin, dragon fruit, lilikoi kombucha, and CBD oil. Featured on Guy Fieri’s Food Network show Diners, Drive-ins and Dives, Down the Hatch also boasts the longest happy hour in Maui. It takes place daily from 2 p.m. to 6 p.m. and features specials on appetizers, draft beers, and select cocktails.

Fleetwood Mac front man Mick Fleetwood is behind this bar and restaurant, located on a third-floor rooftop in Lahaina. Here, guests sip drinks under beige umbrellas while taking in views of the dreamy blue Pacific. To pair with award-winning cocktails like the Heart of the Jungle (Cynar, Velvet Falernum, coconut rum, and lemon juice), which comes in a tiki artichoke, executive chef Eric Morrissette serves a menu of elevated bar bites, fresh local fish, and meatier dishes like filet mignon with peppercorn reduction. If you’re not a cocktail person, know that the robust drink menu also features beers from Maui Brewing Co. and Kohola Brewing as well as exclusive wines like Krug Brut from Reims, Luberri Gran Reserva rioja, and even a Chateau Musar red blend from Lebanon.

Set within the 24-acre oasis of Montage Kapalua Bay, this pop-up bar and lounge pairs Veuve Clicquot Champagne with Maui’s world-class sunsets. Open Thursday through Sunday from 3:30 p.m. to 7 p.m., the Champagne Hale (pronounced HAH-leh, which is the Hawaiian word for house) serves a range of bubbly, from Veuve’s signature Yellow Label, Rosé, and La Grande Dame labels to special Rich and Rich Rosé offerings, available for the first time on the island. Pair your sips with light bites like Kualoa Ranch oysters, bigeye tuna tartare, and burrata toast with pickled strawberries and pistachio pesto, then take in the views as the sun goes down over the Pacific. From the bar’s clifftop perch above Namalu Bay, you’ll enjoy stunning vistas of the ocean as well as Molokai and Lanai islands in the distance.

This elegant bar at the Andaz Maui overlooks tiers of pools, waterfalls, and tropical foliage, all cascading down to the Wailea coast. Hotel guests and visitors alike come here to lounge under umbrellas by day and around a fire pit by night, sipping on cocktails like the Upcountry Buck (white rum, ginger, and pineapple) and the Lahaina Town Fizz (blanco tequila, strawberry, and elderflower). For something unique, try the Silversword, a cocktail designed by legendary Hawaiian mixologist Julie Reiner that features mezcal, sweet vermouth, pineapple, and chocolate bitters. Pair it with snacks like chilled shrimp summer rolls and Thai lettuce wraps, then finish with a ginger ice cream sandwich made in-house.

Every Saturday from 7 a.m. to 1 p.m., the island’s largest open-air market sprawls across the University of Hawai‘i Maui College campus, creating a lively scene with more than 200 vendors. Many of Maui’s best boutiques sell their wares here, but for much cheaper prices than at their brick-and-mortar locations. Browse for muumuus, wood carvings, and other handmade crafts like bone and shell jewelry, or treat yourself to a shave ice while perusing piles of leis, local fruit, and homemade baked goods. The market is especially strong when it comes to street food—don’t miss the spam kebabs, banana bread, and goji kombucha.

Open since 1932, this pit stop on the road to Lahaina is most famous for its Hawaiian hot dogs. They’re just standard red franks, grilled and stuffed in a bun, but Maui’s pro surfers and their fans—who usually stop here on their way to Olowalu Beach—have elevated the snack to almost cult status. If you’re not one for hot dogs, the general store also sells boiled peanuts, shave ice, and Spam musubi, along with an abbreviated Mexican menu when the kitchen’s cranking. In between bites, take time to browse the shop’s collection of locally made souvenirs and appreciate its unique decor. A late employee had a soft spot for starving artists and would often trade food for artworks, asking only that the pieces incorporated his favorite vehicle—a Volkswagen Beetle.