The insider advice on this page is from Wendy’s Trusted Travel Expert for California and Hawaii: Jay Johnson of Coastline Travel Advisors.
Jay spends six weeks a year in Hawaii, escorting groups of Google execs as well as vacationing with his wife Dani—who’s also his right hand in the office—and their teenaged daughters. His agency sends so many travelers to Hawaii that he has significant clout with the five-star resorts—which translates into perks for his travelers—but he also books rental homes when that’s the smarter choice for the group. He can arrange anything from multi-generational family reunions to pull-out-all-the-stops honeymoons, from kite-boarding lessons on Maui to guided hikes across private land on Molokai. Born and raised in Southern California and with offices throughout the Golden State, Jay also likes to orchestrate out-of-the-box itineraries in his own backyard. He 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.
Where to Stay and Eat
Hotel 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, we can arrange for our guests who stay five nights or more to receive a $100 per night resort credit. One other tip: 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.
Best bang-for-your-buck hotel
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 we can 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 just three of my 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.
I’m a simple guy who loves a great pizza and beer, so when I discovered Sale Pepe on my last trip to Maui, I was hooked. It’s 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 (my wife’s favorite is the udon in a rich broth) as well as a large collection of sake.
We love Leilani’s fish tacos—so much so that we’ll usually go back multiple times during a single trip. The roasted tomatillo aioli is delicious. Grab a seat at the beachside grill; they don’t serve the tacos in the dining room.
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
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.
Despite their popularity, most luaus feel staged to me and don’t offer an authentic Hawaiian experience.
Spend the afternoon with a local of native Hawaiian descent on Molokai, a remote island with no stoplights, nor buildings taller than a coconut tree. We’ll whisk you there by private yacht, and you’ll be invited into the home of one of Molokai’s native Hawaiians for lunch; there, you’ll hear the story of a family that has lived on the island—considered the most traditionally Hawaiian of the state’s eight main islands—for many generations. You can spend the balance of the day hiking to waterfalls on the eastern end of the island (on private property that you can’t access on your own), and visiting some of Molokai’s local shops, which sell exquisitely carved wooden bowls.
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.
The weather is best in April, May, September, October, and November.
Unless you don’t mind crowds or wasting money, avoid spring break.
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.
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.
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!
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.
Our favorite things to bring home typically don’t last long but sure are appreciated: Chili Pepper Water (hot sauce) from Hula Grill and 100% pure Kona Coffee.