As your plane makes its descent into Maui, threading the space between the island’s two volcanoes and flying over a landscape of craggy rock, lime tree orchards, and lush rainforest, it becomes immediately clear that this island is about much more than beaches and mai tai’s. Of course, one can travel to Maui for a restful escape but for those who like a busy schedule, this island has more than enough on offer. Wine tastings, chocolate tours, surfing, kayaking, hiking, waterfall hikes, and eating, lots of eating. This is the guide for those who appreciate the beach but want to explore everything else as well.
As a test of the up-to-date authenticity of my reporting, I asked OpenAI/ChatGPT to write about the best things to do in Maui – the “story” was correct, to a point. It did not include several new offerings on the island, or the best guides and programs to consult when doing the predictable things (knowledge that can only be derived from an actual experience), and there was zero information about the lesser known offerings – such as the really cool chocolate tour we took. All of this to say, this written-by-a-human–who-actually-visited article promises to be worth both your time and mine.
Get a Guide
This is the first order of business if you really want to understand and experience what you are looking at and enjoying in Maui. Our first guided expedition was up to the top of Haleakala—the long, winding ascent to the top of the island’s still-active volcano (at 10,000+ feet elevation) is a miracle of nature. A guide will share with you the fact that you’ll pass through ten different climates before reaching the summit. We hired Humble Tours to drive us to the top, provide a lunch and ferry us to the various highlights of the volcano. It’s a seven-hour adventure with short hikes into viewing platforms and through a very ethereal eucalyptus forest.
We also secured a guide from Hike Maui for our kayak/snorkel/waterfall hike trip (which was everyone’s favorite experience) – a full-day that started with an amazing kayak experience out to a reef. Our guide anchored the boats and took us on a snorkel tour – pointing out every kind of sea creature (many of which were camouflaged and we would have missed.) The Hike Maui team then squired us to Twin Falls for a guided nature and waterfall hike. Our guide for this experience was an avid naturalist and pointed out all of the edible plants, which we were happy to try, along the way to our waterfalls.
Wine and Chocolate
The Maui Chocolate Tour is a fascinating look inside a chocolate plantation (this might be an overstatement, it’s more of a “farm”) and how cacao beans are cultivated, harvested and turned into chocolate. A tour of the cacao grove is followed by a tasting of nine different single origin chocolates in their cool treehouse.
Upcountry Maui is an intriguing part of the island, given its unusual climate (a product of being midway between the summit of Haleakala and sea level). Here you can visit Maui Wine – reservation suggested – for a tasting of local wines. Cooler temperatures yield interesting options such as the Chenin Blanc from their Ulupalakua vineyards.
Adventures in Eating
The intersection of cultures that has defined the history of the Hawaiian Islands is most prominent in the fabulous range of culinary offerings on the island. For the most local, multicultural immersion be sure to book at table at Tiffany’s Restaurant & Bar. it was by-far our favorite meal of the visit. The dining room is comprised of locals and the menu is manifestly global in nature. Chicken and Waffles features okuzuya wings with waffles drizzled in umami butter or try the Bi Bim Bap with seasonal Maui vegetables. A succulent pork shank is twice fried and served with ginger garlic tonkotsu sauce, and the smoked ahi tuna dip with Kula onion, capers and chives is a must-have starter. Wash it all down with a Lilikoi Yuzu Tropical Seltzer (a collaboration between Lanikai Brewing and Matsumoto Shave Ice)
For a more special occasion experience book an oceanfront meal at Cane & Canoe, the refined dining experience at the incomparable Montage Kapalua Bay delivers locally infused modern spin on Hawaiian cuisine in a stunning setting. We loved the lamb in a tandoori sauce, from-scratch taro root bread with local Maui honey Taro and the pristine Hamachi Crudo with mango calamansi, aji Amarillo and pickled Fresno chili. The sun sets as your meal progresses and once night falls order a night cap and wander down to the shoreline. The Montage dims the shoreline lighting – all the better to see the dazzling night sky. This meal was our farewell dinner, and the combination of setting and culinary artistry was the perfect end to our family vacation.
In between those two experiences, we popped into the festive, convivial atmosphere of Monkeypod Kitchen—where we had the absolute best Mai Tai of the trip (a drink we sampled in every establishment). The lacy layer of honey foam atop the drink sealed the deal. Cocktails are a must here, but the dishes deliver as well. A straightforward menu of offerings (lobster deviled eggs, margherita pizza, bulgogi pork tacos) is complimented by highlights such as the pork chop with French curry and roasted pineapple or the savory Siamin noodle bowl in earthy broth with pulled pork.
For a coffee and one of the island’s best avocado toasts visit the newly-opened Momona Bakery and Café. The generous portion of avocado toast is a meal for two, and the buttery pastries rival any French bakery for quality.
Lahaina Fish Co. is a two-story al fresco dining experience that overlooks the Pacific. The menu features a broad menu of seafood classics but be sure to try their signature mahi mahi fish sandwich – served on a buttery toasted brioche bun with Swiss cheese and homemade coleslaw. If you make it all the way to Hana, look for the food trucks. Among them you’ll find Ae’s Thai Kitchen. Tuck into any one of Ae’s classic Thai dishes, but the panang chicken was spectacular.
Accommodating an entire family in a hotel room has its challenges; booking a condo or villa with kitchen and extra bathrooms is the better option for a kinder, gentler vacation experience. Kaanapali Alii, a Destination by Hyatt Residence, offers nicely appointed condominiums with pretty ocean views and all of the standard hotel amenities (except for dining). You’ll get daily housekeeping, valet, fitness center, tennis courts and oceanfront pools. You can also request everything from sunscreen to extra towels and dish soap—a concierge is on hand to assist in planning activities, and don’t miss the rise and shine yoga and beachfront grilling – a Poolside Grill master is on hand at select hours each day to grill your meal. And, if the on-site offerings aren’t enough for you, the property is also just steps away from several other resorts and dining options as well as the Whaler’s Village open-air mall.