Island Guide: How to Choose the Right Hawaiian Island

by Shellie Bailey-Shah

Don’t know which island to choose for your family vacation? Here’s our island-by-island guide.

The Hawaiian archipelago, consisting of eight main islands, sits 2285 miles off the USA mainland in the Pacific Ocean. Five of these islands are idyllic settings for family vacations. Like the Hawaiian people themselves, each island has its own distinct personality. Don’t know which one to choose? Here’s a guide that explains what each has to offer families with kids in terms of activities, resorts, and food.

Wave coming in on the Big Island of Hawaii
Photo: Tor Johnson, Hawaii Tourism Authority

1. Big Island of Hawaii

Why go to the Big Island?

As the name implies, the Big Island is the largest and most diverse of the Hawaiian Islands. I’d recommend spending the majority of your visit on the Kona side (west) with its stark lava fields and mega resorts but also book a few days on the Hilo side (east). It’s wetter, more lush, and closer to Volcanoes National Park. The Big Island is one of the only places in the world where you can see rivers of molten lava running into the sea!

Where to stay on the Big Island?

Surprisingly, not every beachfront hotel has beach access on the Big Island. Fairmont Orchid near Waikoloa does. Green sea turtles bask on its sugar sand beach every afternoon. The hotel has a pool, outrigger canoes, paddleboards, snorkeling, tennis, and golf. The Keiki Aloha children’s program caters to kids (ages 5-12). The hotel offers archeological hikes to the nearby petroglyph fields. Starts at $239/night.

On the Hilo side, consider a stay at Hawaii Volcanoes Treehouse. Perched 20-feet high in a rainforest canopy, this one-of-a-kind resort for adventure-seeking families is just outside the national park. Children must be at least 6 years old to stay. Starts at $225/night.

What to do on the Big Island?

A visit to Volcanoes National Park is a must. Kilauea has been erupting since 1983. The red-hot lava flows are sometimes visible, especially after dark. When hiking here, make sure to wear closed-toe shoes. And don’t pocket any lava rocks or Pele, the goddess of the volcano, will curse you with bad luck!

Tour the Kona Coffee Living History Farm near Captain Cook to understand why coffee is king on the Big Island.

Take the twisting Saddle Road to the top of Mauna Kea for stargazing at the observatory. From Hilo, it’s a 90-minute drive. Keep in mind, you’ll be driving back down in the dark. Dress warmly; it’s cold at the 13,796-foot summit.

Kid playing in the surf on a beach in Maui

2. Maui

Why go to Maui?

A popular destination for visitors, the Valley Isle of Maui is the perfect playground for an active family. With sailing, snorkeling, surfing, and exceptional resort pools, pack your swimsuits and sunscreen for this island paradise.

Where to stay on Maui?

For pampered luxury, it’s hard to beat the Ritz-Carlton Kapalua. This high-end property is best for families who plan to stay at the resort to enjoy the pool and beach rather than explore other attractions. Rates start at around $391/night. Read our full review here.

Also lovely, the Hyatt Regency Maui Resort and Spa, located in Ka’anapali, offers a kid-friendly pool with slides and a lazy river, hula lessons, and lei-making classes. Or your kids can boogie board the day away on the hotel beach. Rates start at $212/night. Read our full review here.

Also in Ka’anapali, you’ll find family favorite Westin Maui Resort and Spa. The pool area here is killer with five pools and two slides, but it also boasts a sandy beach. Rates start at $359/night. Read our full review here.

In contrast to the high-rise resorts, Napili Kai Beach Resort offers plantation-style suites with ocean views. From its crescent-shaped and reef-protected beach, you can swim with turtles. Rates start at $335/night. Read our full review here.

Finally, Kamaole Sands in south Kihei on Maui’s southwestern shore is budget-friendly option. The sprawling, beautifully-landscaped condo complex is less than half the price of other condo properties, in addition to being close to shopping, dining, and island activities. Starts at $161/night. Read our full review here.

What to do on Maui?

For families with kids of any age, take a snorkeling trip with Four Winds II out of Ma’alea Harbor to Molokini, a submerged crater and marine preserve. The catamaran has a water slide and glass bottom viewing room. In addition to beautiful fish and turtles, you may see a pod of Humpback whales on your trip! Of snorkel Black Rock near the Hyatt Regency on your own.

Hike the Twin Falls Trail, featuring waterfalls, swimming holes, and one of the better snack stands on the road to Hana.

Looking for some truly authentic Hawaiian experiences? Read our top 6 picks.

Read what our KidTripster Teen thinks of Maui.

Where to eat on Maui?

Much of the food at Maui’s best restaurants is sourced locally, so get ready for fresh from the sea and farm fare. Oh, and don’t worry, we know where the best shave ice on the island is, too. Check out our favorite 7 spots.

Aerial view of Waikiki Beach in Oahu
Photo: Tor Johnson, Hawaii Tourism Authority

3. Oahu

Why go to Oahu?

From Pearl Harbor to Waikiki to Diamond Head, Oahu promises a legendary Hawaiian holiday. Nicknamed the “Gathering Place,” the island is the most urban and most visited of the Hawaiian Islands. Along with history, it offers families a hefty dose of Hawaiian hospitality.

Where to stay on Oahu?

Let’s start in Honolulu’s Waikiki area. If you’re looking for luxury, head to the Royal Hawaiian Hotel or Halekunlani. But why not save a little money and opt for budget-friendly and recently-renovated Courtyard Waikiki Beach or Aqua Aloha Surf Hotel. Rates start at $269 and $99, respectively. Read our reviews here.

Then there’s the famed North Shore for a quieter, more authentic Hawaiian experience. Here we recommend the Courtyard Oahu North Shore, a newer hotel with a fabulous resort feel. Rates start at $220. Read our full review here.

Less hectic than Honolulu, the Ko Olina resort area on the leeward (east) coast of Oahu boasts several properties including Marriott’s Ko Olina Beach ClubFour Seasons Resort Oahu at Ko Olina, and Beach Villas at Ko Olina. All of these resorts are located along kid-friendly, beachfront lagoons that are great for swimming and snorkeling. Read our full review here. Also in this area, you’ll find Disney’s Aulani with a mind-boggling list of kid amenities, plus a dizzying number of pool and water features. Starts at $449/night. Read here why it’s not just for little kids. And more insider tips for getting the most out of your Aulani vacation, click here.

Where to eat on Oahu?

We know where to get the best shave ice on this island, too. Read about all of our 7 top picks.

What to do on Oahu?

Visit the historic sites of Pearl Harbor to fully understand the events that pulled the USA into World War II. Remember to buy your tickets in advance online.

The most popular hike on Oahu is the Diamond Head Summit Trail, but it may be too strenuous for young families. Alternatively, consider an easier trek to Pali Lookout for panoramic vistas or Makapu’u Point Lighthouse Trail for tide pools and possible glimpses of whales breaching offshore.

Famed Waikiki Beach boasts the best weather on the island, but the white sands of Kailua Beach offer something for everyone without the huge crowds. Read about all of Oahu’s best family beaches here.

Canyon in Kaui

4. Kauai

Why go to Kauai?

Once a secret paradise, Kauai – also known as the “Garden Island” – has been discovered! If your family is looking for unparalleled natural beauty and nature experiences, Kauai is your destination.

Where to stay on Kauai?

Grand Hyatt Kauai Resort and Spa is an ideal family retreat. While it doesn’t have a swim beach, it does have a saltwater lagoon and gorgeous pool with waterfalls and slide. There are also kayaks, tennis, golf, and Camp Hyatt with its colorful parrots. Rates start at $475/night. Read our full review here.

Sitting along Kalapaki Beach, Kauai Marriott Resort is a full-service resort for families who are completely content to spend their vacation in one spot. Case in point, the weekly activity guide here is four pages long – double-sided, no less! Read our full review here.

Centrally located in KapaaWaipouli Beach Resort and Spa by Outrigger is a more budget-friendly option. These well-appointed condos offer separate bedrooms, separate bathrooms, living room, laundry, and full kitchen. (There’s a grocery store across the street.) It has a meandering swimming pool with water slides and a toddler area plus beach access. Starts at $229/night.

What to do on Kauai?

If you’re going to take a helicopter tour, Kauai is the island to do it, as most of Kauai’s beauty can only be seen from the air. Fly over Waimea Canyon, the Grand Canyon of the Pacific, and the breathtaking Na Pali coast. Alternatively, you can take in the breathtaking views of the gorge from Waimea Canyon Lookout.

KidTripster Tip: Many operators offer a zodiac boat ride along the Na Pali coastline, originating in Waimea or Princeville. While these small rafts offer access inside sea caves, the ride is too long and too bumpy to actually be enjoyable. To be honest, I was far too panicked about my 12-year-old’s ability (and my own, frankly) to hold on and not fall off to enjoy the stunning scenery. I wouldn’t do this activity again and can’t recommend it for families. Alternatively, if you want to see the Na Pali coast, choose a company that uses large boats. Also make sure there’s a snorkeling opportunity for the kids as a reward for all that sightseeing.

Tunnels Beach near Princeville is a perfect beach for small children, as the water is very shallow. But be aware: parking can be a nightmare. Go early.

For the best price and selection, rent bikes (kid sizes, too) at Hele On Kauai Bike Rentals in Kapaa. Then cycle the eight-mile Kapaa Bike Path that hugs the coast.

We’re not done! Here are 7 more must-dos in Kauai, including a one-of-kind tubing adventure that I guarantee your kids will love!

Where to eat on Kauai?

What? More shave ice? Yes! On Kauai, you must try Waikomo Shave Ice plus these other spots that round out our Top 10.

Green water and rocky coastline in Lanai
Photo: Don Riddle

5. Lanai

Why go to Lanai?

Lanai is the smallest Hawaiian island open to visitors. In 2012, Larry Ellison, founder of Oracle, purchased 98-percent of the island with the remaining 2-percent owned by the State of Hawaii. If you family has been to Hawaii multiple times before and is feeling like, “been there, done that,” then this may be the island for you. A quiet, no-crowds vacation, Lanai will serve as your own private island.

Where to stay on Lanai?

In my opinion, the only luxury family choice is the Four Seasons Resort Lana’i at Manele Bay. Perched atop a red lava cliff, the hotel caters to families with a kids’ camp, teen center, snorkeling, tennis, and golf plus gifts for the kids. Rates start at $875/night.

What to do?

Take a free shuttle to Manele Bay’s sister property, Four Seasons The Lodge at Koele. In this countryside setting, enjoy horseback riding, golf, miniature golf, and croquet.

Getting there

It’s best to combine a trip to Lanai with Maui. From Maui, you take a 40-minute ferry to the island. If you travel from December to April, you’ll have an excellent chance of spotting whales along the way.

bright red flower in Hawaii

Best times to visit Hawaii

High season is generally from mid-December to mid-April. Expect more crowds and more expensive rates. Low seasons are spring and fall; that’s when Hawaii enjoys its best weather. If you do go during the winter, pack a wetsuit for the kids, as water temperatures can be a bit nippy. But never fear, there’s also a healthy dose of golden sunshine.

This writer received some complimentary stays, activities, and meals for the purpose of this review. However, all opinions expressed are solely her own.

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