I’ve hopped to Oahu, Maui, Kauai, the Big Island, plus Lanai and Molokai. I went with family once, with my partner twice, and solo when I needed quiet. I got sunburned. I ate too much poke. I got car sick on one very twisty road. So which island is “best”? Tricky. Each one sings in a different key.
Short answer:
- First trip or mixed group? Oahu.
- Couples or “treat yourself”? Maui.
- Nature and quiet? Kauai.
- Adventure and science nerd joy? Big Island.
- Off-grid calm? Molokai.
- Luxe and hush-hush? Lanai.
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Let me explain.
If you’re curious about every little test I ran on each island—cost spreadsheets, snorkel scores, and all—you can peek at my detailed trip diary right here.
How I Actually Tested Them
I stayed in condos and hotels. I rented small cars and one dusty Jeep. I snorkeled with my own Cressi mask. I used reef-safe zinc sunscreen (Kokua and Raw Elements worked). I ate local—Foodland poke, Leonard’s malasadas, shave ice pretty much everywhere. I booked a few tours, but I also wandered. That mix told me a lot.
Oahu: Big Energy, Big Variety
My first morning in Waikiki, I grabbed spam musubi from 7-Eleven and watched the surfers. It was busy, yes, but fun. Later, I ate a plate lunch at Rainbow Drive-In and hiked Diamond Head at sunrise. Not hard. Great view. Pearl Harbor moved me more than I expected. I left quiet, and grateful.
When I needed calm, I took the bus to the North Shore. I sat at Sunset Beach with a fresh garlic shrimp plate from a truck. In winter, the waves roared like a train. In summer, it was a pool. Beach-hunters can scope my candid rundown of the best beaches on Oahu for more sandy specifics.
Pick Oahu if:
- You want easy flights, lots of food, and nightlife.
- You have kids or mixed ages.
- You like museums and beaches in the same day.
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Heads up: Hanauma Bay needs a reservation. So does Diamond Head for parking. I learned that the sweaty way.
Maui: Love Notes and Long Roads
I went to Maui with my partner. We did the Road to Hana. It’s gorgeous and winding. I got a little green in the face after 300 curves, but the bamboo forest and the black sand at Waiʻānapanapa made me forget fast. We ate fresh banana bread from a tiny stand. Warm. Sticky. Perfect.
Sunrise at Haleakalā made me cry a little. I wore three layers and a beanie, and it was still cold. If you plan to catch that dawn glow, remember that the park now requires an advance permit—grab yours through the official National Park Service reservation system. After, we got pancakes in Kula with mac nut syrup. That syrup felt illegal, in a good way.
We snorkeled Molokini on a calm day. Clear water like glass. I saw a parrotfish that looked like it was painted by a kid with neon markers.
Pick Maui if:
- You want romance.
- You like long, pretty drives and a bit of luxe.
- You want soft sand and easy snorkeling.
Got a bachelorette party on the horizon? I rounded up my favorite celebratory spots (with some hits and hilarious misses) in this guide.
Note: Parts of Maui, including Lahaina, are healing. Be kind. Spend with local businesses. Ask before you share locations.
Kauai: The Green Quiet
Kauai felt like a deep breath. We stayed in Hanalei and woke to rain on the roof. I hiked the first part of the Kalalau Trail to Hanakapiʻai Beach. Mud found my socks in five minutes. Worth it. The cliffs looked like a movie. Actually, many movies.
One afternoon, we pulled over at Wailua Falls, then ate taro doughnuts from Holey Grail. They were crisp on the outside, tender inside. I still dream of the lilikoi glaze.
I kayaked the Wailua River with my cousin. We saw a sleeping turtle near the bank. We whispered thanks and left it be.
Pick Kauai if:
- You crave nature, waterfalls, and slower days.
- You don’t mind rain here and there.
- You like small towns and chickens everywhere. Yes, the roosters are your alarm clock.
Tip: Hāʻena State Park (for Keʻe Beach/Kalalau) needs a pass. Book it. Don’t wing it like I did once. We ended up getting poke and sitting on the pier instead, which was still sweet.
Big Island (Hawaiʻi Island): Lava and Stars
This island feels huge. We split time—Hilo side for lush, Kona side for sun. In Hawaiʻi Volcanoes National Park, I walked through steamy earth and felt the ground hum. Not scary. Just alive. We waited for sunset at the Jaggar area, then watched the sky go purple. I whispered, “Wow,” like five times. Couldn’t help it.
At night in Kona, I swam with manta rays. They swooped like huge velvet blankets. I held onto a float, breathed slow, and tried not to squeal through my snorkel.
We toured a Kona coffee farm. I learned the difference between medium and dark roast by taste, not by label. I liked medium. Who knew?
Pick Big Island if:
- You love geology, space, and science.
- You want black sand beaches (hello, Punaluʻu).
- You like variety: waterfalls in the morning, lava fields at noon, stars at night.
It’s spread out. Plan your drives. Bring snacks. My “hanger” was real on Saddle Road.
Lanai: Whisper-Level Luxury
I took a ferry from Maui to Lanai and rented a Jeep. We rattled down a red dirt road to Shipwreck Beach. The wind felt wild. We saw the rusted ship and a monk seal snoozing far down the shore. We kept distance, of course.
Lunch was quiet. Even the birds sounded soft. If you want hush and sand and maybe a splurge at the Four Seasons, this is your place.
Pick Lanai if:
- You want calm and comfort.
- You like light crowds and hidden corners.
Molokai: Real Slow, Real Strong
Molokai was the least touristy for me. I visited the Saturday market and bought banana bread from a grandma who asked about my family. We took a guided visit to Kalaupapa and learned hard history with care. I felt humbled and small and grateful to listen.
Pick Molokai if:
- You want community over resorts.
- You’re fine with simple stays, big heart, and few shops.
So… Which Island Do I Call “Best”?
For most folks, I say Oahu first. It’s the sampler plate. You can try city, surf, culture, and food, then come back for a deeper cut.
For my own heart? It’s a tie: Kauai for peace, Big Island for wonder. I know, that’s cheating. But trips aren’t math. They’re moods.
Little Things I Learned the Hard Way
- Book key spots early: Haleakalā sunrise passes, Hanauma Bay, Hāʻena State Park.
- Reef-safe sunscreen matters. Your skin and the fish say thanks.
- Bring water shoes. Lava is sharp, and hidden urchins are spicy.
- Respect closures and wildlife space. A selfie is not worth a fine—or a turtle’s stress.
- Motion sickness tabs saved me on the Road to Hana and the Molokini boat. Truly.
Quick Picks by Traveler Type
- Families: Oahu or Maui. Easy beaches, lots of food, plenty of shade.
- Hikers: Kauai. Pack for mud. Smile anyway.
- Science buffs: Big Island. Volcanoes, stars, coffee farms.
- Honeymooners: Maui (with a Lanai day).
- Introverts: Kauai north