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Choosing the Perfect Hawaiian Island for Your Trip

Choosing the Perfect Hawaiian Island for Your Trip

We'll never forget our first time planning a trip to Hawaii. Staring at that cluster of islands in the middle of the Pacific, it's easy to feel a bit lost. Should you go to the one with the active volcanoes, the one with the legendary surf breaks, or the one famous for romance and waterfalls?

The truth is, each of Hawaii's main islands offers a completely different world. Picking the right one is the key to planning a trip you'll talk about for years.

After exploring them all, we've learned the unique personality of each island. This isn't just another list; this is a practical guide to help you choose the perfect island for your kind of travel. We'll break down the vibe, the must-do experiences, and who each island is best for, so you can plan your trip with confidence.

Oahu is for you if you want a mix of city life, world-famous beaches, incredible food, and important U.S. history. Maui is for you if you're looking for upscale resorts, a legendary road trip on the Road to Hana, and some of the best whale watching on the planet. Kauai is for you if you crave raw natural beauty, with dramatic cliffs, powerful waterfalls, and some of the most rewarding hikes in the state. The Big Island is for you if you're seeking diversity and adventure, from active volcanoes and black sand beaches to lush rainforests and epic stargazing. Lanai & Molokai are for you if you want an authentic, off-the-grid experience to truly get away from the crowds.

Oahu is energetic and bustling, with a vibrant mix of city life, world-famous beaches, and lush mountains. It's best for first-time visitors, families, foodies, and anyone who loves having endless activity options. Don't miss Pearl Harbor, the surf scene on the North Shore, and the iconic Waikiki Beach.

We weren't sure what to expect from Oahu, thinking it might just be the big city and crowded beaches. But we were wrong. We spent a humbling morning at Pearl Harbor, which is an experience that stays with you, and then drove up to the North Shore. Watching the legendary surfers at Waimea Bay, grabbing lunch from a shrimp shack… that's where we found the real soul of the island. It's a place of incredible contrasts.Beyond the city, Oahu boasts an incredible number of hiking trails for all skill levels, from easy coastal walks to strenuous mountain ridges.* Pay Respects at Pearl Harbor: A visit to the Pearl Harbor National Memorial is a moving and essential experience. It's a powerful reminder of a pivotal moment in history, and we think it's one of the most important sites to see in the entire state.* Hike Diamond Head: This is one of the most iconic hikes in Hawaii for a reason. The trail takes you to the rim of a volcanic crater, delivering incredible panoramic views of Waikiki and the turquoise coast. Just remember to book your spot in advance.* Explore the North Shore: Escape the energy of Honolulu and drive up to the legendary North Shore. In the winter, you can watch professional surfers tackle some of the biggest waves in the world. In the summer, the water is calmer, and the vibe is pure, laid-back surf town.* Experience Waikiki Beach: Yes, it's busy, but Waikiki is a spectacle you have to see at least once. It's a great place for a first-time surf lesson, to see the historic Duke Kahanamoku statue, and to just soak in the scene.For Luxury: Halepuna Waikiki by Halekulani - This hotel feels like a calm oasis just steps from the action of Waikiki. We liked the clean, modern design and the infinity pool is a great place to relax. It's a high-end choice that delivers on service and style.For a Social Scene: Polynesian Hostel Beach Club - If you are on a budget or travelling solo, this is a solid choice. It's not fancy, but the location is fantastic, just a few minutes' walk from the beach. It's a good place to meet other travellers.Maui is for you if you're looking for a mix of luxury, epic road trips, and unbelievable wildlife encounters. It has been voted the 'best island' by readers of Condé Nast Traveler for over 20 years, and it has a well-deserved reputation for world-class resorts and romantic getaways. While it's perfect for romance, Maui is also fantastic for families, with plenty of activities to keep both kids and adults entertained.
Maui was the first Hawaiian island we ever visited together, and it set an incredibly high bar. We did the Road to Hana, of course, but the moment that really stands out is from a whale watching tour. We were floating in a small catamaran when a massive humpback whale breached right off the bow. The sheer power and grace of it is something that photos can’t capture. It’s that mix of serene beauty and raw nature that makes Maui so special.Our Favourite Things to Do on Maui:• Drive the Road to Hana: This is one of the best road trips in the world, full stop. The highway twists along the island's north coast, taking you past countless waterfalls, through dense bamboo forests, and around hairpin turns with breathtaking ocean views.• Watch the Sunrise at Haleakala?: Driving to the summit of the dormant Haleakala volcano to watch the sunrise from 10,023 feet is an unforgettable experience. You are literally above the clouds. Reservations are required well in advance, but it is absolutely worth the early start.• Go Whale Watching: From December to May, thousands of humpback whales migrate to Maui's warm waters. Taking a boat tour to see them is a must. We found the best time to go is between January and March when sightings are practically guaranteed.Where to Stay on Maui:• For Luxury: Four Seasons Resort Maui at Wailea If you are looking to splurge, this is one of the best resorts on the island. Located in the upscale Wailea area, the service is top-notch, and the beachfront location is hard to beat.• For a Laid-Back Vibe: Paia Inn For something more boutique and less of a mega-resort, we enjoyed the town of Paia on the north shore. Paia Inn is a chic hotel right in the heart of this cool little surf town, making it a great base for exploring the Road to Hana.• We have a full accommodation guide for the island of Maui to help you plan your trip.Kauai: The Garden IsleThe Vibe:* Wild, untamed, and breathtakingly beautiful. This is where nature is the main attraction.Best for:* Adventurers, serious hikers, landscape photographers, and anyone looking to be humbled by nature.Don’t Miss:* The N?pali Coast (by boat or air), the vast Waimea Canyon, and the legendary Kalalau Trail.The Experience:Kauai is for the adventurers and nature lovers. This island is all about raw, dramatic beauty, and it’s noticeably less developed than Oahu or Maui. If your idea of a perfect day involves a challenging hike, discovering a secluded beach, or just marvelling at unbelievable scenery, Kauai is for you.We thought we’d seen dramatic landscapes before, but nothing prepares you for Kauai. We splurged on a doors-off helicopter tour, and it was worth every penny. Flying into the lush, green cathedral of the N?pali Coast, with its razor-sharp cliffs and countless waterfalls, is a core travel memory for us. It feels like a land forgotten by time. If you’re looking for true, jaw-dropping adventure, this is the island.

Our Favourite Things to Do on Kauai

  • Hike the Kalalau Trail: This is one of the most famous and difficult hikes in the United States, tracing the cliffs of the legendary N?pali Coast. You need a permit and plenty of experience, but for those who are prepared, the views are some of the best we’ve ever seen.
  • Explore Waimea Canyon: Known as the “Grand Canyon of the Pacific,” this massive canyon is a spectacle of red and green canyon walls. You can drive up to several lookouts for fantastic views or take one of the hiking trails down into the canyon itself.
  • Take a Helicopter Tour: So much of Kauai’s interior is inaccessible by road or trail. A helicopter tour is a big splurge, but it’s the only way to truly appreciate the scale of the island and see the waterfalls of Mount Waialeale.

Where to Stay on Kauai

  • For Luxury on the South Shore: Koloa Landing Resort at Po’ipu: Located on the sunnier south side of the island, this resort is a great upscale base. The pools here are fantastic, and it’s well-positioned for exploring Waimea Canyon.
  • For a North Shore Base: Hanalei Bay Resort: If you want to be closer to the lush landscapes of the north, this resort offers incredible views of Hanalei Bay and the mountains. It feels a bit more old-school Hawaii and is the perfect starting point for adventures along the N?pali Coast.
  • If you want more in-depth information about hotels on Kauai, check out our accommodation guide for the island.

Big Island of Hawaii: The Adventure Isle

Quick Summary

  • The Vibe: Diverse, dramatic, and constantly changing. A land of fire and ice, with active volcanoes, lush rainforests, and stark lava fields.
  • Best for: Road trippers, adventure seekers, and anyone who wants to see nature in its most raw, creative state.
  • Don’t Miss: Hawaii Volcanoes National Park, night snorkeling with manta rays, and the unique green and black sand beaches.

Of all the islands, The Big Island is for the true adventurer who wants to see nature at its most powerful. It’s twice the size of all the other islands combined, and you can find 10 of the world’s 14 climate zones here. If you want a trip that’s less about lying on a beach and more about exploring and being amazed, this is your island.

Dave & Deb’s Take

The Big Island is just that—big. You can drive from a sunny beach through a lush rainforest and into a cool, misty volcanic landscape all in one afternoon. But the most surreal experience for us was the night snorkel with manta rays. Floating in the dark water while these massive, graceful creatures glide inches below you is pure magic. It felt like something from another world. This island is all about those unforgettable, one-of-a-kind adventures.

Our Favourite Things to Do on the Big Island

  • Explore Hawaii Volcanoes National Park: This is the number one reason to visit the Big Island. It’s the only place in Hawaii where you have the chance to see active, flowing lava. We’ll never forget standing at the Kilauea caldera at night, watching the red glow of the lava lake pulse against the dark sky.
  • Snorkel with Manta Rays at Night: This sounds a little intimidating, but trust us, it’s one of the most magical wildlife encounters we’ve ever had. You hold onto a lighted raft while these gentle giants, with wingspans up to 15 feet, glide and somersault right below you.
  • Explore the Coloured Sand Beaches: The Big Island is famous for its unique beaches. The jet-black sand at Punalu’u, created by volcanic activity, is incredible to see. It is also home to Papak?lea, one of the few rare green sand beaches in the world. We loved seeing the massive honu (Hawaiian Green Sea Turtles) that often rest on the warm black sand at Punalu’u.

Where to Stay on the Big Island

  • For Volcano Access (East Side): Volcano Inn To make the most of the national park, we recommend staying nearby for a night or two. We loved the Volcano Inn; it’s a cozy spot tucked into the rainforest, just minutes from the park entrance. This makes it super easy to drive back to the caldera after dark to see the lava glow.
  • For Beaches and Resorts (West Side): The Westin Hapuna Beach Resort The sunny Kona-Kohala coast is the island’s resort hub. This hotel is situated on Hapuna Beach, which is one of the most beautiful white-sand beaches in all of Hawaii. It’s a great place to relax after a few days of volcanic adventure.

Lanai & Molokai: The Undiscovered Isles

Quick Summary

  • The Vibe: Quiet, authentic, and rugged. This is where you go to experience Hawaii as it once was, away from the hustle.
  • Best for: Getting off the grid, digital detoxes, and experiencing a slower, more local way of life.
  • Don’t Miss: Exploring the rugged landscape of Lanai with a 4×4; learning the profound history of the Kalaupapa Peninsula on Molokai.

The Experience

These islands are for the traveller, not the tourist. Molokai is best known for its authentic vacation experience, receiving just a fraction of the visitors that the other islands do. If you are looking to disconnect and experience a more intentional way of life away from any resort scene, this is your place.

Similarly, Lanai is for the traveller who truly wants to get away from it all. The island has a quiet, exclusive feel. If your goal is to unplug, explore rugged landscapes, and feel like you have an entire island to yourself, Lanai is the spot.

Visiting Lanai and Molokai feels like stepping back in time. We rented a Jeep on Lanai and spent the day driving rugged dirt roads to empty beaches without seeing another soul. It’s a different kind of Hawaii experience, one that’s less about resorts and more about quiet exploration and connecting with the land. These islands aren’t for everyone, but if you truly want to unplug and see a more authentic side of Hawaii, they are unforgettable.Our Favourite Things to DoRent a 4x4 and Explore: This is a must. Drive the unpaved roads to places like Keahiakawelo (Garden of the Gods), a bizarre and beautiful landscape of red rock formations.Relax at Hulopoe Bay: This protected marine reserve is the island’s best spot for swimming and snorkeling, and we saw a huge pod of spinner dolphins just offshore.On Molokai:Visit Kalaupapa National Historical Park: A visit here is a powerful history lesson about the former leprosy settlement. The landscape is hauntingly beautiful, and you must book a tour with a certified guide.Walk Papohaku Beach: At three miles long, this is one of Hawaii’s longest white-sand beaches, and you will likely have it all to yourself.Where to StayOn Lanai: Four Seasons Resort Lanai Perched on a cliff above Hulopoe Bay, it’s the definition of a five-star escape. For a more charming and affordable option, check out the Hotel Lanai in Lanai City.On Molokai: Hotel Molokai This is the island’s best-known place to stay. It’s a charming, rustic hotel with Polynesian-style bungalows that have a real old-school Hawaii vibe.Practical Tips for Visiting HawaiiA little planning goes a long way in Hawaii. Here are a few key things to keep in mind.A Note on Responsible TravelVisiting Hawaii has changed in recent years, and we think it’s for the better. There’s a big focus on regenerative tourism, which is all about giving back to the local communities and helping to protect the incredible natural environments you’re coming to see.How to Get Between the Hawaiian IslandsWith the exception of a passenger ferry that runs between Maui and Lanai, the only way to get from one island to another is to fly. Hawaiian Airlines is the main carrier and offers a busy schedule of short, frequent flights between all the main islands. We recommend booking these inter-island flights well in advance, especially during peak season, as they can fill up.

Do I Need to Rent a Car?

For every island except Oahu, the answer is a definite yes. To properly explore Maui, Kauai, the Big Island, Lanai, and Molokai, a rental car is essential. On Oahu, you can get by without one if you plan to stay exclusively in the Honolulu and Waikiki area, but you will need a car to explore the beautiful North Shore and the rest of the island.

While every island offers something special, the “best” one truly depends on your travel style. The purpose of our guide is to help you match your personal preferences—be it adventure, relaxation, or city life—with the island that delivers that experience best.

For most first-time visitors, Oahu is a great choice. It’s easy to fly into and offers a huge variety of activities. If you’re more of an adventurer, the Big Island is another fantastic option as it gives you a taste of everything: volcanoes, beautiful beaches, and lush rainforests.

Start by identifying your top priority. Are you looking for epic hikes (Kauai), nightlife and history (Oahu), luxury resorts (Maui), or volcanic adventure (Big Island)? Use our guide to match your travel style to an island’s personality.

Most people would give the title to Kauai. Its nickname is “the Garden Isle” for a reason. The dramatic, green-velvet cliffs of the Na Pali Coast and the sheer scale of Waimea Canyon are truly unforgettable.

Choose Oahu if you want more action, nightlife, restaurant choices, and historical sites. Choose Maui if you’re looking for a more laid-back, upscale, and romantic vibe with world-class resorts and incredible nature experiences.

This choice comes down to nature versus city. Choose Kauai if you want to be immersed in raw, natural landscapes and spend your days hiking and exploring. Choose Oahu if you want the amenities of a major city, famous surf culture, and a wider variety of dining and entertainment.

Choosing the right Hawaiian island is the first and most important step in planning your trip. There really is no single “best” one, only the island that’s best for you. Whether you’re looking for the city buzz of Oahu, the romance of Maui, the raw beauty of Kauai, or the volcanic adventure of the Big Island, Hawaii has an island that will feel like it was made for you.

We hope this guide has helped you find your perfect match.

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