Poor Maui.  She wins a lot of beauty contests, but she can’t get a date.  More precisely, she cannot get your “date” for your President Club incentive trip.

Conde Nast Traveler readers rated her #1 for 20 consecutive years!  So, she is a beauty in the eyes of leisure travelers, but meeting planners and sales execs seem to look all over for the shiny, up-and-coming, youngster (meaning a new resort or destination, of course).

Are we chasing after “new” when the “best” is right in front of our eyes?  (As a side note, new destinations often lack incentive quality infrastructure, whereas Maui has a well-oiled tourism machine.)

I recently returned from the IRF Invitational, which was graciously hosted by the Grand Wailea and co-sponsored by multiple Maui hotels and DMCs.  The 2017 Invitational set all-time records for attendance and popularity – gathering over 500 attendees, including 200+ buyers from the largest incentive/meeting companies and corporate end users.  The record attendance by this A-list group of whos-who in incentive travel is proof of the motivational draw of Maui.

A few years ago, I wrote another Hawaii incentive travel article recommending:

“Visit a different Hawaiian island every three years…for top-ranked islands popular with your employees and a varied mix of world class experiences.”

Here’s a quick, 60-second update of Maui incentive resort options.  First, let’s glance at the main tourist spots below.


If luxury is what you’re seeking, there is no shortage of 5-star, incentive-quality resorts along the southern end of the island.

Grand Wailiea in Maui
Grand Wailea, a Waldorf Astoria Resort

First, a gigantic “mahalo” for hosting the 2017 IRF Invitational!  “Grand” is the keyword.  At 780 guest rooms, it is the best option for big groups. Small groups could get lost (or alternatively enjoy the privacy of not seeing each other).  The pool could be a mini-water park, so it’s a great option for groups with families. The Wailea beach is wide and gorgeous.

Fairmont Kea Lani

Fairmont Kea Lani

What I love about this resort for groups is the run-of-house rooms are all suites (at 860 sq. f each), which makes every attendee feel like they got a VIP upgrade.  It’s a nice added value. The recently renovated Willow Stream Spa wins many awards.  Another “mahalo” here for hosting an incredible IRF silent auction and outdoor dinner overlooking Polo Beach!

Four Seasons Maui

Four Seasons Resort Maui

Their Forbes five-star and AAA five–diamond rankings tell meeting planners everything about the best-in-class guest service this brand is known for. The complimentary amenities (cabanas, sunscreen, lounge entertainment) make the entire group feel like VIPs, and they don’t require extra effort or expense from meeting planners. Fantastic service.  Excellent dining options – Ferraro or Spago might be the best sunset views on the island.  Mahalo for hosting our IRF Board of Trustee meeting and dinner!

Marriott Wailea Beach

Wailea Beach Resort – Marriott

This is the new kid on the block.  Actually, it was the first hotel in Wailea, but Marriott just plunked down $100 million for a top-to-bottom transformation of its 547 rooms.  Honestly, it seems like they spent twice that.  As an incentive planner, what makes this resort unique are its special event venues.  The picture here is the Luau Gardens, where they graciously hosted our IRF Evening Reception.

Andaz Maui

Andaz Maui at Wailea Resort

Opening in 2013, Andaz still feels like a new, cool kid on the block (or beach).  Modern, minimalist design feels like W meets Maui.  This was Hyatt’s first resort opening of their lifestyle collection of boutique hotels.  Beach is secluded by massive rock formations and native trees.  Event kitchen could be used for a unique live appetizer station.


In the middle (geographically and cost) is Kaanapali with a broad selection of 4-star resorts – Hyatt, Westin, and Sheraton – along with walking distance shopping and restaurants at Whaler’s Village – which makes this area a home run for incentive groups with lots of free time and needing to stretch their budget.

Sheraton Maui

Sheraton Maui Resort & Spa

Don’t overlook this Sheraton. It’s the very best Sheraton I’ve seen. The property has low-rise buildings with ample lawns and large pool area, so the resort feels very spacious. The beachfront snorkeling is the best of any resort, and the nightly cliff diver off Black Rock is pretty cool.

Westin Maui

Westin Maui Resort & Spa

The Heavenly Beds always make incentive attendees feel right at home.  Kaanapali Beach was rated the #1 Beach in the USA a couple of time, so groups enjoy beautiful sand and lots of water activities.

Hyatt Regency Maui

Hyatt Regency Maui Resort

We’ve hosted several club trips here. The Sales team is very flexible and works hard to build win-win budgets. We love the beach walk along Kaanapali Beach. Whalers Village intersects the walkway with affordable shopping options.


Kapalua on the north side has two 5-star luxury resorts in a more secluded environment.  The trade winds often make Kapalua  3-4 degrees cooler than Wailea.

Ritz-Carlton Kapalua Maui

The Ritz-Carlton Kapalua

The Ritz sits by itself up north on Kapalua.  The plus: group rates are often very attractive, and it’s a retreat setting.  The minus: not much nearby.  The Ritz beach, P.T. Fleming, is award winning.  And, golfers love the PGA quality courses.

Montage Kapalua Bay Maui

Montage Kapalua Bay

What makes the Montage so unique is what it doesn’t have…lots of rooms filled with lots of people. The resort features only 50 suites – and each one is an exquisitely designed 1, 2, or 3 bedroom suite.  The result? An amenity-packed resort that offers exclusivity usually reserved for celebrities and rock stars.


Travaasa Hana Maui

Travaasa Hana

Most people know the famous “road to Hana” – but few ever stay the night.  For the right kind of group, this secluded and “chill” resort would offer a one-of-a-kind incentive trip.  The rooms are all cabins or bungalows.  The vibe and atmosphere feel like you have completely unplugged.

Here is an infographic highlighting the top incentive travel ideas for Maui.

Maui Infographic from Spear One

Mike May

Author Mike May

President | Author of 12.5 Steps to a Perfect Incentive Program. Expertise: bucket-list incentive trips, motivational incentive program design, matching event goals with the perfect destination & hotel, cost savings strategies, global channel reward programs, and targeted communications.

More posts by Mike May

Leave a Reply