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Maui, Hawaii: Insider’s Guide

by | January 24, 2019

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 teenaged 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 kite-boarding 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.

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.

Covid safety intel

Jay and Dani are helping travelers choose private rentals homes and condos, or bungalow-style accommodations at hotels that have lots of outdoor space; most opt to rent a car, which makes social distancing easy. They’re advising travelers to avoid Honolulu, but they can arrange a private tour of Pearl Harbor with a masked guide if requested. Dani visited Hawaii in early December so that she could see firsthand how her favorite hotels, restaurants, and activity operators are handling the pandemic.

Where to Stay and Eat

Hotels worth the splurge
The Four Seasons Resort Maui at Wailea has the best location on the island and a superb staff. It’s beloved by both honeymooners, who appreciate the candlelit, beachfront restaurant and the adults-only Serenity Pool, and families, who can take full advantage of the hotel’s complimentary kids club. And though it’s one of the priciest hotels on the island, at certain times of year Jay and Dani can arrange for their travelers who stay five nights or more to receive a $100-per-night resort credit. Unless you plan to spend a lot of time inside, don’t bother springing for a room with a full ocean view—you’ll be more than satisfied with a partial ocean-view.

Families might also consider starting their trip with a few nights at 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.

Four Seasons Maui balcony

Four Seasons Maui. Photo: Four Seasons

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! (Some of the Whaler’s condos can be booked through the Aston, but Jay and Dani get preferential rates for some of the privately owned units.)

Restaurants the locals love
Lahaina may be the main tourist town of Maui, but its wealth of good restaurants draws plenty of locals too. Here are three favorites:

Not too many places specialize in pizza and seafood—for good reason—but Honu does both well. Set right on the waterfront, Honu is a friendly, family-run place that turns out delicious oyster cocktails, crab mac and cheese, brick-oven pizzas topped with locally grown mushrooms or house-made sausage, and so much more.

Sale Pepe is run by a Brooklynite and an Italian who were married on Maui and eventually came back to open a restaurant; the chef is a graduate of the prestigious Scuola Italiana Pizzaioli.

Tucked away in the more industrial part of Lahaina, Star Noodle has noodle dishes from all over Asia (especially tasty is the udon in a rich broth) as well as a large collection of sake.

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.

Mamas Fish House North Shore Maui Hawaii

Mama’s Fish House, North Shore, Maui. 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. The menu changes based on each day’s catch, and it even lists the fisherman responsible for bringing in each dish.

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.

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.

Don’t bother
Despite their popularity, most luaus feel staged, and don’t offer an authentic Hawaiian experience.

Best for thrill seekers
Kanaha Beach, just outside the main town of Kahului, is a perfect place to try kite boarding 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.

Contact Jay and Dani

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Best Times to Go

The weather is best in April, May, September, October, and November.

Worst Time to Go

Unless you don’t mind crowds or wasting money, avoid spring break.

Biggest Rookie Mistake

Not planning your trip to Hana well. The famous “Road to Hana” has lots of twists and turns—literally. There are 54 bridges and some 600 curves! In order to really enjoy it, you need to start by 5 a.m. so that you can stop along the way and still be back by evening; though you can’t see every scenic waypoint in a single day, be sure not to miss the Seven Sacred Pools, where waterfalls empty into pristine swimming holes.

Word of Warning

Any boat trip that offers an all-inclusive program with water sports, meals, and alcoholic beverages is sure to be more booze cruise than wildlife adventure. If you want to see some fish, opt for an early-morning snorkeling trip via catamaran instead.

Road Intel

If you are renting a car, sign up to receive text message alerts regarding the County of Maui’s Road Closure Notifications. There is only one highway in and out of the main beach areas, including Kaanapali. You’ll want to know if there are any delays so you avoid sitting in traffic on your vacation!

Don’t Forget to Pack

Binoculars to check out the breaching whales up close. Though they’re usually around between December and April, February and March are peak whale season in Maui.

The Souvenirs

Chili Pepper Water (hot sauce) from Hula Grill and 100% pure Kona coffee. They typically don’t last long, but sure are appreciated.


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