Hawai‘i is more than just a tropical paradise—it’s a place where history, culture, and natural beauty come together in powerful ways. Once an independent kingdom ruled by Native Hawaiian monarchs, the islands became the 50th U.S. state in 1959, but they’ve held tightly to their rich cultural identity. From the ancient traditions of hula and the spiritual significance of ʻāina (land), to the legacy of voyaging canoes and the aloha spirit that shapes daily life, Hawai‘i offers a deep and vibrant cultural experience. Whether exploring sacred heiau (temples), enjoying a lūʻau, or learning about the islands’ complex past, visitors will find that Hawai‘i’s story is as layered and meaningful as its landscapes.

The Same

From romantic cliffside sunsets to kid-friendly snorkeling coves, here’s how we rank the four major Hawaiian Islands—Kauai, Big Island, Maui, and Oahu—with summaries and our take from both travel phases of life.

Kauai

Kauai is the oldest and lushest of the Hawaiian Islands, known for its jaw-dropping natural beauty, remote beaches, waterfalls, and the dramatic cliffs of the Na Pali Coast. It’s a slower-paced, nature-heavy escape—ideal for hiking, kayaking, and scenic solitude. Kauai is a perfect blend of relaxation and natural adventure for both couples and families. It earns the top spot.

• SEE: Helicopter tour over the Na Pali Coast was the ultimate romantic thrill. Calm beaches like Poipu and Salt Pond made ocean time stress-free. A catamaran cruise let everyone enjoy the Na Pali views without the hike
• EAT: Kaua‘i Shrimp – Sustainably farmed on the island, these sweet, plump shrimp often show up in garlic butter plates or poke bowls. They’re fresher here than anywhere else.
• DRINK: Kauaʻi Beer Company – A laid-back Līhuʻe brewery serving small-batch craft beers with a local twist, perfect for unwinding after exploring the island.

Get both of our full take on this beautifuly island

Two Different Takes on Kauai, Hawaii

Big Island (Hawaii)

Twice the size of all the other Hawaiian Islands combined, the Big Island offers raw, powerful landscapes, from active volcanoes to black sand beaches to lush rainforest and even snow-capped mountains. It’s the most geographically diverse island. Incredible for exploration and older kids, but requires more planning and stamina than the other islands.

Get both of our full take on this adventurous island

• SEE: Volcanoes National Park and lava flows were otherworldly; Green Sand beach
• DRINK: Kona Coffee on a farm tour or Kona Brewing Company: Experience Hawaii’s world-famous coffee at its source, strolling through lush plantations and tasting fresh brews straight from the roaster. A Big Island favorite, Kona Brewing offers tropical-inspired beers and a breezy pub setting just steps from the Kailua-Kona waterfront
• EAT: Macadamia Nuts – While they grow across the islands, the Big Island produces them in the largest quantity. Stop by the Mauna Loa Macadamia Nut Factory for flavored varieties and treats like chocolate-covered nuts.

Double Take on Hawaii’s Big Island: Adventures, Relaxation & Family-Friendly Escapes

Maui

Maui blends natural beauty with resort luxury. Home to the famous Road to Hana, Haleakalā sunrise, and world-class beaches, it’s a balanced option—somewhere between raw adventure and curated comfort.

• SEE: Road to Hana – waterfalls, bamboo forests, and epic views all day. Romantic sunrise atop Haleakalā and sunset dinners in Wailea
• EAT: Banana Bread on the Road to Hāna – Tiny roadside stands along this scenic drive sell warm, fragrant banana bread—moist, sweet, and sometimes made with local additions like coconut or macadamia nuts
• DRINK: Ocean Vodka & Maui Brewing Company – A scenic upcountry Maui destination where you can tour an organic vodka distillery and sample award-winning island-brewed beers in one stop.

Get both of our full take on this amazing island

Two Takes on the Road to Hāna(Hawaii): Waterfalls & Other National Wonder

Oahu

Oahu is home to the state capital of Honolulu, the iconic Waikiki Beach, and historical landmarks like Pearl Harbor. It’s the most populated and accessible island, great for first-timers and those wanting a blend of beach and city life. Perfect for families, especially first-timers. Less relaxing or romantic for couples wanting seclusion.

• SEE: Surfing Waikiki and sipping cocktails with Diamond Head views. Escaping to the North Shore helped break up the hustle. So many kid-friendly attractions: Honolulu Zoo, Dole Plantation, Polynesian Cultural Center
• EAT: Garlic Shrimp from the North Shore, Spam Musubi, plate Lunch at Rainbow Drive-In, and Malasadas from Leonard’s Bakery
• DRINK: Waikiki Brewing Company – A lively Honolulu brewery known for its creative craft beers, casual atmosphere, and great people-watching near the beach.

Get both of our full take on this busy island

Two Sides of Oahu, Hawaii: A Guide to North Shore and South Shore Experiences

The Dinks

Hawaii is one of those destinations that sticks with you. Each island has its own vibe, strengths, and surprises. Here’s how we rank the Hawaiian Islands based on our experiences, with a little bias thrown in (because how could you not fall in love with paradise?).

1. Maui – Where It All Began (for Us): We’re definitely partial to Maui, it’s where we got engaged, on the black sand beach along the iconic Road to Hana. But even without the personal connection, what’s not to love? Maui offers a stunning mix of natural beauty and resort luxury. From watching the sunrise atop Haleakalā to exploring upcountry farms and beaches that suit every mood, the island is romantic, adventurous, and effortlessly relaxing all at once. The Road to Hana may be a bit wild to drive, but it’s unforgettable in all the best ways.
2. Big Island – Volcanoes, Coffee & Pure Adventure: Where else can you visit an active volcano, sip world-famous Kona coffee, and snorkel with manta rays all in one trip? The Big Island truly lives up to its name, with dramatic landscapes that feel like stepping onto another planet. Volcanoes National Park is a must-see, and the black sand beaches and lava fields offer a raw, rugged beauty. Add in a thriving local craft coffee and beer scene, plus incredible stargazing from the summit of Mauna Kea, and you’ve got an island that delivers big on both nature and experience.
3. Oahu – Urban Energy Meets Island Beauty: It can feel a little hectic, but Oahu has it all; beaches, culture, nightlife, and history. Waikiki is iconic (if a bit crowded), while spots like Diamond Head and Pearl Harbor add meaningful depth to your visit. Oahu strikes a unique balance, offering a mix of bustling urban life in Honolulu with more laid-back vibes on the North Shore. It’s incredibly convenient for families, first-timers, or anyone wanting a little bit of everything without having to hop islands.
4. Kauai – A Quick But Gorgeous Glimpse: We only stayed two days on Kauai, so it didn’t get a fair shot—but what we did see was breathtaking. Known as the Garden Isle, it’s lush, green, and practically made for outdoor lovers. The cliffs, waterfalls, and scenery are nothing short of dramatic, with the Na Pali Coast offering some of the most jaw-dropping views in all of Hawaii. Kauai feels quieter and more remote, which makes it ideal for those seeking nature-forward adventures and a slower pace.

The Family

We visited all of the Hawaiian Islands before having kids, but as a family, we’ve only returned to Oahu, the Big Island, and Kauai with our children. Here’s how we rank the islands based on both our couple and family experiences.

1. Oahu: In general, Oahu stands out as the best Hawaiian island for families with kids thanks to its wide variety of activities that appeal to all ages. From beaches to cultural sites and kid-friendly entertainment, there’s something for everyone to enjoy together. One of our favorite resorts ever Aulani, A Disney Resort & Spa. While it’s not cheap, we found it to be a great value. The calm beach is perfect for little ones, with boogie boards and sand toys available. The pool complex is fantastic, featuring a lazy river, tube slides, splash zones, and one of the best kids’ clubs we’ve seen. The resort also offers a packed schedule of family-friendly entertainment and character experiences. Another bonus? There are affordable dining options nearby, which helps balance out the cost. And if you’re looking to save on flights, consider earning the Southwest Companion Pass and 110,000 miles—it’s a game-changer for flying to Hawaii for free.
   • Get the full details on how we make our trips to Oahu Affordable
2. The Big Island: The Big Island is a fantastic destination for families, especially if your kids are a little older and ready for more adventurous experiences. We’re glad we waited until ours were old enough to fully appreciate everything the island has to offer—from exploring active volcanoes and hiking through lava tubes to night snorkeling with manta rays and visiting coffee farms. The island’s size means more driving between attractions, but older kids tend to handle that better, especially when the reward is a black sand beach, a waterfall hike, or a glowing lava flow. There’s also great educational value here, with opportunities to learn about geology, Hawaiian culture, astronomy at Mauna Kea, and marine life. If your family is up for a bit more exploration and adventure, the Big Island delivers in a big way.
3. Kauai: Kauai offered our family the perfect setting to slow down and simply relax. We stayed at a resort on the beach, where the vibe was peaceful and laid-back—ideal for unwinding together. While Kauai is known for its outdoor adventures, we focused more on enjoying the resort’s amenities, lounging by the pool, and taking easy beach strolls. The natural beauty of the island surrounds you at every turn, so even a low-key day feels special. With a calm pace, fewer crowds, and lush scenery, Kauai was a refreshing change that allowed us to recharge as a family without a packed itinerary.

Summary

Hawaii isn’t just one destination . . . it’s a collection of island experiences, each with its own personality, pace, and appeal depending on your travel style and stage of life. Whether you’re planning a romantic escape, an outdoor adventure, or a family-friendly getaway, each of the four major islands—Kauai, the Big Island, Maui, and Oahu—offers something unique. From the lush tranquility of Kauai to the volcanic drama of the Big Island, the balanced luxury of Maui, and the bustling energy of Oahu, we’ve explored them all as both a couple and a family. This blog shares how our impressions have evolved over time and how each island ranks for us based on our personal experiences, with tips to help you decide which Hawaiian island might be the best fit for your next trip.