Where to Eat, Stay and Play in Maui if You've Visited the Island Before

Even if you’re a frequent visitor to Maui, there’s always something new to discover on this Hawaiian island paradise.


Winning (or #winning, if you do the hashtag thing) — that sums up vacationing on the Hawaiian island of Maui, because everything about it is amazing: the beaches, the ocean, the waterfalls, the resorts, the food, the weather, the activities — the list goes on and on. 

After a long, frigid Calgary winter, Maui bestows a much-needed tropical break to restore mental and physical well-being, as well as moisture to lizard-esque skin. But what if you’ve already “done” Maui? First off, it’s impossible to ever be “done” with Maui. Even if you’ve gone frequently, there’s always something new to discover, whether you’re looking to satiate your sense of adventure, your taste buds or your inner yogi. 

The key is to rub shoulders with locals who have that aloha spirit of warmth, friendliness and sincerity. They’ll help you navigate the best of Maui and share the spiritual significance of island experiences, making it all the more meaningful for you. 

What To See and Do in Maui 

Stand-Up Paddleboarding

Stand-up paddleboarding (SUP) is less taxing than swimming and less ego-crushing than surfing. For feeble swimmers (yours truly), the first SUP experience might better be described as “KDP” (kneel-down paddleboarding); however, any terror you might feel will morph into delight once you paddle up alongside your first sea turtle with a beach umbrella-sized shell. While you can rent a board to try on your own, a better approach is to have a local guide show you the ropes. 


Heli Tour

photograph courtesy of Blue Hawaiian Helicopters 

Get a bird’s-eye view of the island from a helicopter.

If you want a fresh perspective on the island, a helicopter tour provides a bird’s-eye view, as well as access to new terrain. Peering down at the world’s largest dormant volcano, for instance, is a completely different (and totally awe-inspiring) experience than hiking to Haleakala Crater. Throw in hidden waterfalls, the lush rainforest of the Keanae region and the iconic Keopuka or “Jurassic Park” rock (from the opening sequence of the movie), and you’ll have panoramic island vistas permanently etched in your mind. Blue Hawaiian Helicopters offers 30-minute to two-hour tours with experienced and knowledgeable pilots. 


Outrigger Canoeing


Experience local culture in an outrigger canoe.

Outrigger canoeing is big time in Hawaii, a proud display of culture and athleticism. For non-natives, it may seem daunting to propel an authentic, 400-pound racing canoe, but the friendly guides at Maui Paddle Sports make you feel wonderfully competent. (“If you suck, I will tell you,” jokes my guide, Jamie — at least I hope he’s joking, but given that my five-year-old daughter is aboard, I figure he won’t judge too harshly). Eventually, you’ll develop a steady paddle rhythm and slice through the ocean, stopping to check out sea turtles and watch locals jump from rock cliffs. Pure fun. 

Download the Gypsy Guide Maui app for an audio-guided GPS tour of the Road to Hana —it’s easy to use and very educational.



Maui’s healthy yoga scene will revive your prana (life energy). Yoga retreats abound, particularly in the Paia area on the north shore, but many resorts also offer convenient drop-in classes. The Westin Maui Resort & Spa’s studio classes are open to the public, while its sister property, the Westin Ka’anapali Ocean Resort Villas, holds outdoor classes for guests (as does the Grand Wailea) so you can listen to ocean waves while you literally salute the sun. For a calendar of yoga classes and events on the island, check out the community events page of the website for the lululemon store in Lahaina.

Where to Eat  

Leoda’s Kitchen and Pie Shop

photograph courtesy of leoda's kitchen and pie shop

Macnut chocolate praline pie, oh my! After devouring a few of these, your life is complete. It’s not just the dessert pies that are amazing here; so, too, are the savoury pot pies. Leoda’s also cooks up melt-in-your-mouth seared ahi-on-rye sandwiches and taro veggie burgers. Located right off the Honoapi’ilani Highway outside Lahaina, this charming, fresh-food kitchen on a plantation-style property is 100 per cent worth the stop. 


Joey’s Kitchen

Located in an unassuming corner of the food court at Whaler’s Village in Ka’anapali, Joey’s offers tantalizing dishes that are totally unexpected for food-court fare. Chef Joey Macadangdang (formerly with Roy’s and Pineapple Grill) uses fresh, locally sourced ingredients, prepared with Hawaiian and Asian flavours. Try the fall-off-your-fork short ribs, impossibly fresh coconut shrimp and succulent mahi fish tacos, served with a selection of yummy sides like kimchee, slaw and macaroni salad. 


Monkeypod Kitchen

photograph courtesy of monkeypod

For a more upscale option, Monkeypod has hip, modern decor, outgoing staff and a lively atmosphere. Co-owner and chef Peter Merriman is considered a pioneer of Hawaiian regional cuisine, and must-try entrees are the Kiawe grilled ahi steak and the Big Island grass fed rib-eye steak with chimichurri sauce — both served with tangy jalapeno mashed potatoes. The award-winning mai tai, topped with delicious honey-lilikoi (passion fruit) foam, is as tasty as it is strong enough to put hair on your chest. 

Where to Stay

Grand Wailea

photograph courtesy of grand wailea

With its expansive, open-air lobby, seven restaurants, cafés and bars, and the largest spa in Hawaii, the Grand Wailea tempts you to never leave. After recent renovations, the resort makes a lasting impression across its sweeping 40-acre property. Start each day with a scrumptious breakfast in the grand dining room overlooking beautifully landscaped grounds that stretch out to the ocean. Then hit the Wailea Canyon Activity Pool, which isn’t so much a pool as a water adventure park with nine separate pools, waterslides, white-water rapids and the world’s first water elevator. 


Westin Ka’anapali Ocean Resort Villas

photograph courtesy of Westin Ka’anapali Ocean Resort Villas

Not having to cook on vacation is fantastic, but sometimes all you want is a bowl of cereal. A full kitchen makes life convenient (especially with kids), and the Westin Ka’anapali Ocean Resort Villas provide that and so much more. Situated on 26 acres of pristine beachfront, the property blends resort and villa-style living. The four-diamond sanctuary offers a modern full-service spa, several restaurants (including the unique Pailolo Bar & Grill food truck) and well-appointed amenities, yet you can still enjoy your spacious and comfortable villa in privacy. Grill your dinner poolside with fresh herbs from the resort gardens or pick up ready-to-cook items from the on-site fresh food market. 

Travel tips from a Calgarian

Photograph by Carson Tofin


Surfer mama and Honubelle swimwear designer Julia Barnes loves going to Maui for the windsurfing. “Maui is a mecca for [ocean sports] with its laid-back atmosphere,” says Barnes. “The warm and consistent wind, especially in the summer, paired with the turquoise ocean is an unbeatable combination.” 

Growing up, Barnes watched windsurfing movies filmed at Ho’okipa, Maui’s world-famous windsurfing beach. “It had been my dream to go there since,” she says. In 2008, her dream became reality when she married her husband, Everett, on Maui, and now they go at least once a year with their two kids.

The family typically rents a house in Haiku on the island’s north shore or a condo in Kihei on the southwest shore, which is close to what Barnes says are the “best beaches on Maui: Po’olenalena Beach or Makena Beach.” 

On calmer days, Barnes enjoys regular surfing, snorkelling and stand-up paddleboarding. For first-timers to Maui, the Road to Hana is “a must,” she says, with stops for bamboo forest hiking and waterfall swimming. 


This article appears in the March 2016 issue of Avenue Calgary. Subscribe here.


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