Traveling Maui, Your Way

Maui is a bucket list destination with affordable options if you plan it right.


In 1866, Mark Twain spent four months exploring Hawaii as a reporter. His 25 letters about the “Sandwich Islands” were most Americans’ first exposure to the tropical paradise. More than 150 years later, we’re still enchanted by the lure of our 50th state. As Hawaii’s second-largest island, Maui holds particular sway, welcoming 2.7 million visitors in 2017. Although a trip to paradise can come with a high price tag, for planners looking to book a faith-based event on Maui, there are enough options to keep everyone living the dream.

Getting There

Several carriers offer flights to Maui, but Hawaiian Airlines stands out for its hospitality factor. Moderate: Economy class offers free meals, snacks, beer and wine, but you’ll pay for the in-flight entertainment. Top-of-the-line: With individual sleeping pods and entertainment centers, complimentary alcohol and made-to-order meals, a first-class seat makes it feels like you’re on vacation before you’ve even landed. *Tip: On the Airbus A330s and A321s, you can upgrade from Economy to Extra Comfort—a section of seats that offer more legroom, priority services and additional amenities.

Where to Stay

There’s no shortage of spectacular properties all over the island, but two areas are particularly popular with groups: Ka’anapali and Wailea. Moderate: The Westin Nanea Ocean Villas opened in April 2017 on the shores of Ka’anapali Beach. A short drive from downtown Lahaina, the 390-room property offers accommodations with full kitchens and individual balconies, has on-site cultural programs and frequently runs special offers. Top-of-the-Line: Grand Wailea, a 776-room beachfront resort set on 40 acres, is home to the largest spa in Hawaii, a pool area with a swim-in grotto and 19-foot waterfall, and more than 100,000 square feet of indoor and outdoor meeting space. *Tip: Book an evening event at Humuhumunukunukuapua’a—a thatched-roof lagoon restaurant at Grand Wailea helmed by Emmy Award-winning chef Mike Lofaro.

Teambuilding Opportunities

Maui is an outdoor-sports paradise, many of which echo the island’s cultural heritage. Moderate: Owned and staffed by professional surfers, including extended family members of surfing legend Duke Kahanamoku, the instructors at Maui Wave Riders will have your group hanging 10 in no time. Top-of-the-Line: There’s nothing like the feeling of a crew working in perfect synchronicity to bring home the meaning of group effort. Ali’i Maui Outrigger Canoes, located in front of The Westin Ocean Resort Villas in Ka’anapali, is a family-owned operation with experienced hoe wa’a (canoe paddlers), who also compete in open-ocean regattas. *Tip: For consistent, ridable waves, book your group surfing lesson in Kihei—known as “Maui’s little Waikiki.”

Polynesian Show

A trip to Maui wouldn’t be the same without attending a quintessential Hawaiian event. Moderate: On Tuesday and Thursday nights, The Shops at Wailea hosts a free one-hour performance with dances from Samoa, Tahiti and Hawaii. Although there isn’t any food or drink service, it’s a great way to see a show without incurring the expense. Top-of-the-Line: You can’t get much more authentic than Feast at Lele—a spectacular, multicourse luau with tables set up right on the sand at the southern end of Lahaina. Unlimited drinks are also included, and the food, dancers, musicians and servers are all top-notch. *Tip: The Shops at Wailea also offer demonstrations throughout the week on woodcarving and coconut husking, as well as palm-frond weaving, lei-making, and ukulele and hula lessons.