Destination Maui: Top 5 Restaurants to Visit on This Hawaiian Island

In the first leg of our Hawaiian journey, we visited Waikiki for three days before departing for Maui, where we stayed at the Westin Maui Resort. Our hotel was on the western shore of the island, just north of Lahaina, a historic town built on the water’s edge, with a fun mix of t-shirt shops, art galleries, bars and restaurants. As we strolled through town one night, we decided to stop in at Fleetwood’s on Front Street for a cocktail before dinner.

Fleetwood’s on Front Street

KonaFleetwood’s on Front Street is a second-floor restaurant with a third-floor rooftop deck perfect for viewing the sunset. We didn’t have reservations but were lucky to grab the last two remaining seats at the rooftop bar, directly in front of the spot where the bartender mixed an array of amazing looking cocktails. Because I was driving the rental car, I tempered myself and stuck with beer. I was actually thrilled to sample Maui Brewing Company’s Coconut Porter, which was hearty and malty with a real finish of coconut.

Fleetwood’s is named after its rather famous owner. Mick Fleetwood, drummer and founder of the band Fleetwood Mac, bought the restaurant two years ago and has styled it to reflect his passions. The bar on the roof formed a large square, making it exceptional for people watching. The rooftop was so alluring, we ended up having a second round, then, much to our surprise, we heard the sound of bagpipes and a Scottish bagpipe player emerged from the entrance and walked right by us. He took the stage, with the setting sun behind him, and pronounced that Mick Fleetwood had wanted this restaurant to celebrate two things—his love of his native Scotland and his fondness for his home in Hawaii. The bagpipe player then played while the sun faded over the water. The whole experience captured us by surprise. My friends know I’m a fan of sunsets anyway, so seeing this Scottish sunset celebration while imbibing during happy hour made me a bit verklempt. Just when we thought the show was over, the Scotsman introduced a Hawaiian native who blew into his conch and explained the historical ties between the Scottish and the Hawaiians.

Bagpipe

Once the bagpipe player came out, we knew we’d be staying for awhile, so we looked at the happy hour menu and each chose a flatbread to eat at the bar. My date went with the margarita flatbread, a colorful plate of mozzarella, oven-dried tomatoes, sweet basil and shaved parmigiano-reggiano cheese.

I chose the special of the night—the Grilled Tenderloin flatbread. Truly tender slices of beef were accented with sweet onion, blue cheese and wild arugula. This was a savory dish and, paired with the coconut porter, the sunset and the cool vibes of this rooftop deck, was the biggest surprise of our trip.

Maui Pizza

Old Lahaina Luau

On Saturday night, we did what all Hawaiian tourists are destined to do—we attended a Luau! Although billed as the Old Lahaina Luau, there was nothing old about this event. This is one major business, basically a carefully crafted and well-orchestrated night of Hawaiian drinks, dinner, desserts and a show.

Luau

As we lined up to enter the Luau, each person was handed a Mai Tai. The night consisted of an open bar with an assortment of mixed drinks, wines and Hawaiian beers.

Vincent was assigned to our table of eight, and he quickly remembered all our names and kept checking back with us, ensuring we were all having fun and never finishing a cocktail without the next already on the table.

Luau

Our all-you-can-eat buffet was pretty incredible. We savored traditional luau fare such as Pua’a Kalua, a pork roasted in an underground oven, which was so tasty and tender. We helped ourselves to Ahi Poke and He’e (octopus) poke, poi and sweet potato. In addition, we dined on Pulehu Steak and Island Style Chicken, along with Island Crab Salad.

At one point, I counted the tables that surrounded the circular stage where the show would take place. It looked as though approximately 800 people were drinking and dining while the sun set in the distance. Every staff member was eager to help or pose for photos with tourists. The men were shirtless, sporting tribal tattoos and broad smiles. The women wore traditional hula skirts and coconut-shell tops.

As we finished our meal, the circular stage lit up and the show began, with traditional dancing and storytelling about the history of Maui and the islands. The whole experience was so amiable and friendly that, although we were exhausted and suburned after a full day at the beach, we didn’t want to leave.

Charley’s Restaurant and Saloon

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When folks talk about Maui, they often mention “The Road to Hana.” This is a ride through the mountains of the north coast that starts in Hana. The road winds through the hills, with tropical rain forests, waterfalls and steep cliffs always providing an eye-popping view.

This famous road starts in Paia, a little town that appears to be set back in the sixties. A walk down the streets makes you realize there is a little bit of hippie culture and a joy of marijuana in this region. The most famous bar in Paia is Charley’s Restaurant and Saloon, mainly because country legend Willie Nelson is known to hang out there and occasionally performs with bands. We stopped in during the afternoon and enjoyed a beer, but opted to dine next door—Rock & Brews Maui.

Rock & Brews Maui

Rock & Brews Maui

At Rock & Brews Maui, I learned that the Maui Wowie is also a pizza! This spicy pie was packed with punch—the tomato sauce, mozzarella and parmigiana were complemented by spicy pepperoni, pineapple and jalapenos. Each bite burst with spiciness and the saltiness of the pepperoni played off the jalapenos. This was umami at its finest. So delicious. And no, I wasn’t stoned.

Leilani’s Maui

The last night of any vacation is always the saddest night. We walked up the beach to drink and dine at Leilani’s Maui, one of the beautiful, vibrant outdoor cafes that line the beach.

Fish Tacos, Leilanis

I opted for another round of fish tacos. These were made with mahi mahi, and were delicious and tangy. My date went with more comfort food, trying their decadent grilled cheese sandwich, served with ample strips of bacon. Our enjoyable meal was only tinged with the cries of a toddler sitting behind us, and we joked we should turn and tell the kid, “we should be the ones crying, we leave tomorrow!”

Hula PieOur real treat came with dessert, though. We couldn’t leave the islands without trying a slice of Hula Pie. According to the menu, Hula Pie “is what the sailors swam to shore for in Lahaina.” So what is Hula Pie? The bottom layer is made of Oreo cookie crumbs, then filled with macadamia nut ice cream and topped with chocolate fudge and macadamia nuts. Our slice was giant, which was good because we planned to share it. We also loved the colorful plate it was served on, and we needed one souvenir to take home with us, so we were thrilled when we learned we could buy a plate.

The next day, we packed our bags, aloe lotioned our sunburns and boarded the plane to return to the mainland. While our sunburn has faded and peeled, we’ll have our Hula Pie plate forever.

  • Photographs: Jim Breslin