Insider’s Guide to Maui: This Hawaiian Island Excels in Low Season

The insider advice on this page is from two of Wendy’s Trusted Travel Experts for Hawaii: Jay and Dani Johnson of Coastline Travel.

Trusted Travel Expert

Jay and Dani Johnson

Jay and Dani spend six weeks a year in Hawaii, escorting groups of Silicon Valley execs as well as vacationing with their two daughters. Their agency sends so many travelers to Hawaii that it has significant clout with the five-star resorts—which translates into perks for their travelers—but they also book rental homes when that’s the smarter choice for the group. They can arrange anything from multi-generational family reunions to pull-out-all-the-stops honeymoons, from kiteboarding lessons on Maui to private guided hikes on Kauai, the Big Island, and Oahu’s North Shore. Living in Los Angeles and with offices throughout California, they can also orchestrate out-of-the-box itineraries in their own backyard. They can arrange for Los Angeles Angels tickets right behind home plate, V.I.P. access to Disneyland, a cooking lesson with the head chef at Napa’s Michelin-starred Meadowood resort, glamping among the redwoods—or all of the above in one quick, efficient trip.

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Expect trips orchestrated by Jay and Dani to have a 5-night minimum and start at $1,000 per day for two travelers in low season (triple that for Christmas/New Year's), with an additional $500 fee for trips planned less than 60 days ahead.

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Where to Stay and Eat

Relax with an unbeatable view at the Four Seasons Maui. Photo: Four Seasons

Hotels worth the splurge
The Four Seasons Resort Maui at Wailea has the best location on the island (you may recall that it served as the backdrop for White Lotus’ first season) and a superb staff. The adults-only Serenity Pool and main pool are both stunning and provide a great place to relax after a day of exploring. Kids of all ages will love the game room with pool tables, shuffleboard, TVs, and board games. The gym is top of the line. Jay and Dani’s guests receive extra perks, such as a complimentary outrigger canoe experience and monogrammed amenities for children. Spring for a room with a full ocean view; among other benefits, it will allow you to watch the Torchbearer, who each night runs to each torch and lights it. Many kids enjoy racing around the property in his wake.

Families also love the nearby Grand Wailea, where the enormous pool deck is a kid’s paradise, with nine interconnected pools, four waterslides, caves, waterfalls, and even a rope swing. The property was fully renovated in 2024.

Best bang-for-your-buck accommodations
It’s hard to beat the value proposition of a condo, especially for a family who’d rather not have every meal at a hotel restaurant. Aside from having nicely equipped kitchens in all the units, the Kaanapali Alii and the Whaler condominium complexes have fantastic BBQ areas with priceless ocean views—so you can keep an eye on the waves as you’re grilling your fresh mahi mahi! If you don’t need kitchen facilities, you’ll find more economical options on the west side of the island.

Restaurants the locals love
OAO Sushi (pronounced “wow”) serves top-grade fish and is very convenient to the Wailea area; most of the nearby hotels’ complimentary shuttles will drop you off there. On the west side of the island, locals love Miso Phat for sushi. Lineage, near Wailea, serves Filipino and Hawaiian recipes family-style.

Dish to try
Leilani’s fish tacos. The roasted tomatillo aioli is delicious. Grab a seat at the beachside grill—they don’t serve the tacos in the dining room.

At Mama’s Fish House, everything on the menu is the catch of the day. Photo: Dani Johnson

Meal worth the splurge
You can’t go wrong with anything you order at the Polynesia-themed Mama’s Fish House in Pai’a, on the North Shore. The menu changes based on each day’s catch, and it even lists the fisherman responsible for each dish. It’s set right on the beach and many call this the best food on Maui, so it’s popular: Be sure to book at least six months in advance. Jay and Dani prefer to come here for lunch, as it’s a long drive from South and West Maui.

What to See and Do

Don’t miss
Driving up and around Highway 30, along the spectacular and secluded coastline of West Maui. Combine it with a hike to the Nakalele Blowhole, a geyser of seawater forced through an opening in the lava rock. It’s one of Mother Nature’s more impressive waterworks shows.

Take a detour to see the Nakalele Blowhole. Photo: Shutterstock

Maluaka Beach, a.k.a. Turtle Town, on the south shore of Maui. You can snorkel or scuba dive here with turtles, of course, plus a huge array of fish: parrot fish, damsel fish, butterfly fish, eels, tang, and much more.

Best for thrill seekers
Kanaha Beach, just outside the main town of Kahului, is a perfect place to try kiteboarding or windsurfing for the first time. Waves break on an offshore reef, so the sea just off the beach is nice and calm, with great side-shore breezes.

Kiteboarders and windsurfers flock to Kanaha Beach Park. Photo: Shutterstock

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