6 versions of paradise: How to choose the right Hawaiian island for you

Dec 25, 2019

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It’s Hawaii Week at TPG! The Hawaiian Islands have so much to offer travelers, from the sprawling city of Honolulu to quiet black-sand beaches to restaurants serving inventive island cuisine. And it’s possible to pull off a visit to the islands using miles and points. It just takes a little savvy planning and we’ll show you how. Visit TPG’s Hawaii destination hub for links to more stories about getting to the islands, staying on the islands and what to do while you’re there.

No matter where you go in America’s 50th state, Hawaii’s eight large islands (one discourages tourists and one is uninhabited) offer a wide variety of topographies, accommodations, activities and experiences.

But each island definitely has its own vibe. How do you choose between so many different versions of paradise? Here’s a short guide to finding the right Hawaiian island to visit on your next vacation.

Related: These are the best times to visit Hawaii

In This Post

Oahu

Oahu is Hawaii’s most bustling and urban island. It’s home to the state’s largest city and commercial center, Honolulu, which is known for an epic rush hour that sometimes rivals Los Angeles. Within the city limits, Waikiki Beach is the place to see and be seen — shop, dine and enjoy the amenities of huge high-rise resorts.

Oahu Waikiki from Air
The view of Honolulu and Waikiki Beach on takeoff from HNL. (Photo by Leslie Harvey.)

But Oahu’s offerings are more diverse than just Honolulu. The growing resort area of Ko Olina is not as built up and has a variety of accommodations, including Disney’s Aulani Resort and the Four Seasons Ko Olina. On the way to Ko Olina from Honolulu is Pearl Harbor, one of the most visited historic sites anywhere on the islands.

Related: 7 fun things to do on a rainy day in Honolulu

Oahu’s North Shore provides another vibe, downright chill with its beach hopping, food-truck loving, small-town surfer scene. Hikers can find plenty of trails all over Oahu, from the peaks of Diamond Head to less-traveled spots like Makiki Valley or Waimea Valley.

Oahu Waimea Valley Waterfall
Swim in a waterfall in O’ahu’s Waimea Valley. (Photo by Leslie Harvey.)

Oahu’s gateway for travelers, Honolulu International Airport (HNL), has the most air service of any location in the islands, making it the cheapest destination for travelers from the mainland. It also offers the most nonstop flights.

Related: Best ways to redeem points and miles on Hawaiian Airlines

Oahu is best for:

  • First-time visitors to Hawaii
  • Single travelers
  • Large groups
  • Budget travelers

For more Oahu research:

Maui

The second-most-visited island in the state and also its second-largest is Maui, home to the famed Road to Hana, Haleakala National Park and the best whale watching anywhere in the islands in winter months.

Haleakala National Park Maui Sliding Sands
Sliding Sands trail at Haleakala National Park. (Photo by Leslie Harvey.)

For many travelers, a vacation on Maui is the best of both worlds. The island offers some of the same infrastructure, conveniences and activities of Oahu without the traffic and urban sprawl. It’s possible to have an active vacation here and visit a lot of attractions or also just enjoy some island R & R at a resort.

Maui is my top pick for families with kids of school age because of its many activities. It works well for multigenerational groups, because it has experiences that grandparents and grandkids can enjoy, like the Maui Ocean Center or a sunrise at Haleakala National Park.

The island of Maui also has many amazing hotels and resorts at a wide variety of price points. Most are clustered in two major areas — on the Lahaina/Ka’anapali/Kapalua corridor on the northwest side of the island or in Kihei/Wailea farther south.

For its size, Maui offers an impressive variety of hotels for travelers to book a hotel stay with points. Most major chains are represented and many properties offer condo accommodations that work for families or larger groups. The Hyatt Regency Maui, Westin Ka’anapali Ocean Resort Villas, Westin Nanea, Grand Wailea (Hilton) and Andaz Maui have all scored well with TPG contributors and readers.

Hyatt Regency Maui
The Hyatt Regency Maui. (Photo by Leslie Harvey.)

Maui is best for:

  • Travelers with kids
  • Multigenerational travel
  • Anyone looking for resort-based condo properties

For more Maui research:

Hawaii (the Big Island)

Hawaii Big Island with Kids - Black Lava KOA Airport
Approach into Kona International Airport ( KOA) gives visitors a peek at the black lava of the Big Island. (Photo by Leslie Harvey)

The island of Hawaii, called the Big Island, is the largest and newest island in the chain. Because it’s so big, seeing everything requires close to a week but it offers many different travel experiences from day to day.

The vast majority of Big Island visitors stick to the western side of the island near the city of Kailua-Kona and the Kohala Coast, where the large resorts are located. Luxury seekers can enjoy high-end properties like the Four Seasons Hualalai, the Mauna Lani Bay Resort (about to reopen in early 2020 after a major renovation by Auberge Resorts) or the Mauna Kea Beach Hotel. Families on a moderate budget can find ample hotel offerings too. In particular, the Waikoloa Beach Marriott and Hilton Waikoloa Village cater to travelers with kids. Luaus and pool complexes are a big draw.

Hawaii Big Island with Kids - Mauna Kea Beach from Above
The Mauna Kea Beach Hotel’s magnificent white-sand beach. (Photo by Leslie Harvey)

Althoug it’s entirely possible to spend a week on the Big Island relaxing on the beach of a resort, the island can also be an adventure traveler’s paradise. On the northern part of the island, travelers can zipline, take ATV tours, jump into waterfalls, scuba dive or snorkel with giant manta rays, or flume down historic sugar cane irrigation channels.

On the southern part of the island, you can visit Hawaii Volcanoes National Park. The town of Hilo on the eastern side of the island has its own local vibe that can be a great getaway for travelers looking for an authentic Hawaiian experience.

The Big Island is best for:

  • Romantic couples getaways
  • Luxury travelers
  • Adventure seekers

For more Big Island research:

Kauai

Kauai’s lush greenery makes it the most beautiful of all the Hawaiian islands. It is home to waterfalls, hiking trails and a variety of eco-adventures. Most travelers seek out Kauai to avoid the hustle and bustle of Oahu and Maui and have a more unplugged vacation experience.

Kauai (Photo by Summer Hull / The Points Guy)
Kauai. (Photo by Summer Hull/The Points Guy)

Unfortunately, Kauai’s natural beauty also makes it less reliable as a vacation destination. The island’s greenery comes from the substantial rainfall it gets, which makes it possible that your vacation in paradise is a damp one. For that reason, it’s probably best to plan for a longer trip, just in case the weather doesn’t cooperate all of the time.

Hotel offerings on Kauai are ample. For families, the hands-down winner is the Grand Hyatt Kauai in Poipu, known for having one of the best waterslides and pools anywhere on the island. Poipu to the south is home to quite a few other major resorts; Princeville to the north has many others.

Kauai is best for:

  • Romantic couples getaways and babymooners
  • Adventure junkies
  • Relaxation seekers

For more Kauai research:

Smaller Islands: Lanai & Molokai

One of the most private beaches in the world at Kalaupapa National Historical Park in Molokai, Hawaii
One of the most private beaches in the world at Kalaupapa National Historical Park in Molokai, Hawaii. (Photo by Darren Murph/The Points Guy)

Although the vast majority of travelers to Hawaii visit Oahu, Maui, the Big Island and Kauai, there are two smaller islands that tourists can visit as well. Getting to both of them requires a little extra effort, as neither has air service from the mainland.

Lanai, the island owned by Oracle co-founder Larry Ellison, is accessible by boat from Maui. It has two Four Seasons resorts on the island, so it’s also luxurious and pricey.

Molokai, in contrast, has no name-brand accommodations, making it a place of refuge for local residents and travelers looking for authentic Hawaii travel experiences. Molokai has commuter air service from Honolulu International Airport (HNL) and Maui’s two airports: Kahului (OGG) and Kapalua (JHM).

I wouldn’t recommend that travelers head to either of these places until they’ve visited several of the larger Hawaiian islands first. You’ll likely get more out of them (and know which one is the right fit for you) once you have more context to appreciate them.

Hawaii’s smaller islands are best for:

  • Returning Hawaii visitors looking for new experiences

For more Lanai and Molokai research:

Are you planning a trip to Hawaii? Here’s some more advice:

Featured image by YinYang/Getty Images.

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