Incentive Travel Pro: How about Hawaii for the next President’s Club Trip?
Prospect: Hmm. We’ve been to Maui. I don’t think we want to go to the same place.
Incentive Travel Pro: I understand. Here’s something else to think about…

Different Island Experiences

Every Hawaiian island offers a vastly different experience from the other. You shouldn’t think you’ve seen Hawaii after one visit. See island differences below.

Top-Rated Islands of the World

The best of the best lists from Travel + Leisure, Conde Nast Traveler, and TripAdvisor make for good daydreaming – and a good proxy for incentive travelers’ preferences. The CN Readers’ Choice Awards rank Maui #1 in the world for the 20th consecutive year. That’s a winning streak! Kauai is #2; Oahu #8; and The Big Island #10.   The T+L World’s Best Awards list Maui #3 and Kauai #7. Oahu and The Big Island would be #11 and #12 if the T+L list kept going. Bottom line: the Hawaiian islands are popular choices.

Hawaii Incentive Highlights

Maui is the first place to go. It’s rated #1. It gives you a sampling of everything. Not too big; not too small. The Wailea area offers 5-star luxury with the Four Seasons Resort, Fairmont Kea Lani, Grand Wailea, and the new Andaz. Kapalua on the north side has the Ritz-Carlton and a new Montage offering 5-star luxury in a more secluded environment. 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. Famous attractions include sunrise at Haleakala, biking down Haleakala (peddling only 20 times in an hour), the scenic road to Hana, and snorkeling at Molokini Crater.


Oahu will be the most budget-friendly choice. You have lots of 4-star hotel choices on famous Waikiki with Hilton Hawaiian Village, the historic Westin Moana Surfrider, 2 Sheratons, 2 Outrigger hotels, and a few high-end resorts, like the famous “Pink Palace” (Royal Hawaiian Hotel from Starwood’s Luxury Collection). Vast shopping and nightlife options are within short walks. Honolulu airport has the most lift and lowest fares for big groups. Top attractions include USS Arizona Memorial at Pearl Harbor, “Mighty Mo” (USS Missouri), Polynesian Cultural Center, Dolphin swims, Submarine Exploration, snorkel, and sunset cruises, and learning to surf with a beach boy on Waikiki Beach.

Now the variety really gets to swaying in the Pacific breeze. Few travelers have visited these next three islands, so they’re all fresh choices for group incentive travel.

The Big Island is next on my list because we’ve done several incentive club trips here. Resort options include The Four Seasons Hualalai (often rated #1 in all Hawaii and a top 5 resort in North America), Fairmont Orchid, Mauna Lani, Mauna Kea, Waikoloa Beach Marriott, and Hilton Waikoloa Village. It’s called “Big” because it’s largest in landmass and grows by a hundred acres every year as molten magma collides with the ocean in a cloud of steam. Ten of 13 climate zones exist here – such as tropical rainforests, volcanic deserts, sunny black sand beaches, and even a snow-capped mountaintop. Remember how those Arizona golf courses look in the desert? Here, the desert is replaced by black lava fields framing beautiful tropical landscaping, resorts, and golf courses. At some point, everyone should see an active volcano (from a distance!) at Kilauea. Other group activities include Dolphin Quest, sunset cruises, and top luaus.

Kauai_Na_Pali_raftKauai is called the “Garden Isle” with steep cliffs, lush tropical rainforests, and tons and tons of fantastic waterfalls. Jurassic Park was filmed here, which may tell you everything. Kauai has the most outdoor adventures – with kayaking the Wailua River, snorkeling around Poipu Beach, hiking into the green valleys, ziplining, and ATV tours. My personal favorites are the Na Pali Coast motorized raft tours (especially the sea caves) and a helicopter tour over Waimea Canyon, called “The Grand Canyon of the Pacific”. Top group hotels are The St. Regis Princeville, Grand Hyatt Kauai, and the new Koa Kea Resort.

Lanai is away from the crowds and bustle of everyday life. Lanai is the Hawaiian destination of untouched tranquility.  Very few groups, or leisure travelers for that matter, have visited the smallest island that is home to 2 Four Seasons Resorts.  Best of all, it’s less expensive than other Hawaiian islands because of the lower tourism traffic. And, did you know Larry Ellison, CEO of Oracle, just bought 98% of the island? He is pumping millions into Lanai, so it’s getting even better!


My incentive travel recommendation: visit a different Hawaiian island every 3 years… for top-ranked islands popular with your employees and a varied mix of world-class experiences. Decide which of these islands is the perfect fit for your group with these comprehensive guides:

Read eBook: Maui Incentive Travel Guide
Read eBook: Oahu Incentive Travel Guide
Read eBook: Lanai, Kauai, and The Big Island 


incentive trip expert advice hawaii

Mike May

Author Mike May

President | Author of 12.5 Steps to a Perfect Incentive Program and recognized as one of the Top 25 Most Influential People in the Incentive Industry. 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.

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