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Incentive Travel Pro: How about Hawaii for the next President’s Club Trip or Sales Incentive 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…

There are Different Island Experiences

Every Hawaiian island offers a vastly different experience. Do not think you’ve seen all of Hawaii after one visit. Oahu has Waikiki and Pearl Harbor.  On the Big Island, see an active volcano, and check that off the bucket list.  Kauai and Lanai offer seclusion and nature.  And, Maui is not too big and not too small with loads of luxury and delicious dining.

A prominent software company goes to Hawaii every year for its sales incentive trip.  It’s become their company culture.  Aloha and mahalo (thank you)!  We recommend using Hawaii in a regular rotational every 3rd year, such as Hawaii, Caribbean (or Mexico), Europe, and then back to a different Hawaiian island.

Hawaii is the Most Motivational

Another reason to repeat Hawaii is trip achievers love it!  An Incentive Research Foundation survey of sales reps eligible for sales incentive trips ranked Hawaii as the #1 most motivating destination.  Leisure travels always rank it high too.

2023 Update: For the third straight year in the IRF research, Hawaii was the clear winner as the place program participants would most like as an incentive award.  While Hawaii remains very popular, it declined in actual bookings from 2021, which is likely caused by heavy travel to Hawaii when international destinations were restricted and rising airline prices.

The Top-Rated Islands of the World

Conde Nast Traveler Awards Logo
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 ranked Maui #1 in the world for 20 consecutive years at one stretch of time. That’s a winning streak! The T+L World’s Best Awards list of Top 25 Islands includes Maui, Kauai, and The Big Island. Bottom line: the Hawaiian islands are popular choices – and motivational to top-selling sales reps.

The Best Hawaiian Sales Incentive Trip Locations

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, Marriott’s Wailea Beach Resort, and the Andaz Maui from the Hyatt brand family. Kapalua on the north side has the Ritz-Carlton and a Montage resort 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.

Four Seasons Resort

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 Marriott’s Luxury Collection) or Halekulani (from the Leading Hotels of the World brand family). 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, sunset cruises, and learning to surf with a beach boy on Waikiki Beach.

Hawaii Aerial Hotel Beach

Waikiki Beach

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

The Big Island  is next on our list because Brightspot has managed several unique 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, the Auberge Mauna Lani, Mauna Kea (from Marriott’s Autograph Collection), 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, including 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.

Hawaii Volcano Lava

Kilauea Volcano

Kauai  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 – kayaking the Wailua River, snorkeling around Poipu Beach, hiking into the green valleys, ziplining, and ATV tours. 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.” The top group hotels are Grand Hyatt Kauai, Royal Sonesta Kauai (formerly Marriott Kauai), Koloa Landing Resort (an all-suite resort from Marriott), and Sheraton Kauai.

Hawaii Sunset Beach Palm Trees

Hawaiian Sunset

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 the ultra-luxurious Four Seasons Resort Lanai.  Best of all, groups feel like they own the island 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!

Looking for More Recommendations

My sales incentive trip 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 

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Mike May

Author Mike May

Mike is a wearer of many hats. President of Brightspot, author of 12.5 Steps to a Perfect Incentive Program, past Chairman of the Incentive Research Foundation (IRF), and recognized as one of the Top 25 Most Influential People in the Incentive Industry. His expertise includes 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. Mike maintains his certifications in many specialties including Certified Meeting Professional (CMP), Certified Incentive Travel Professional (CITP), and Incentive Professional (IP).

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