The Best Island To Travel To In Hawaii (From My Own Trips)

I’m Kayla. I’ve gone to Hawaii six times. Different islands. Different seasons. I’ve gone with my husband, my mom, and once with my super-sandy toddler who tried to eat a lava rock. So, yeah, I’ve learned some stuff the real way.

Here’s the thing: there isn’t one “best” island for everyone. But there was a best island for me, and maybe for you too. Let me explain.
For the longer breakdown (with even more itinerary details), I put together this exploration of the best island to travel to in Hawaii from my own trips.

The quick answer by traveler type

  • First trip ever: Oahu
  • Nature and quiet: Kauai
  • Adventure with space to breathe: Big Island (Hawaiʻi Island)
  • Beach plus food and a little fancy: Maui
  • True escape, low crowds: Lanai or Molokai

Now I’ll tell you what I actually did, what worked, and what kind of mess I made.

Oahu: easy win for a first trip

Oahu is like a sampler platter. A little of everything, and it’s easy.

What I loved:

  • Lanikai Pillbox hike at sunrise. I parked on Kuailima Drive and walked up. Street parking is tight. I brought a headlamp. The view felt like a screensaver.
  • Hanauma Bay for snorkeling. I booked the reservation and showed up early. The water was calm, and I saw a parrotfish that looked like it was wearing lipstick.
  • Food. Helena’s Hawaiian Food. Giovanni’s shrimp truck. Matsumoto’s shave ice. ABC Stores saved me more than once with reef-safe sunscreen.

Before you go, it’s worth skimming the official Hanauma Bay Nature Preserve website for current hours, fees, and conservation rules.

What bugged me:

  • Waikiki gets packed. I liked staying one block back, so I had quiet at night but could still walk to the beach.
  • Parking costs add up. I used TheBus once to skip a lot.

Small note: Pearl Harbor hit me hard. I walked through the exhibits, and I just got quiet. It’s heavy, but it matters.

Maui: beach days and big views (with a footnote)

Maui is smooth and pretty. It feels like vacation on purpose.

What I loved:

  • Haleakalā sunrise. Yes, you need a reservation. Yes, it’s freezing on top. I wore a winter hat over a messy bun. Worth it.
  • Road to Hāna. I saved offline maps and left at 6 a.m. I stopped at Waiʻānapanapa’s black sand beach (also needs a timed entry). Banana bread at Aunt Sandy’s was still warm. My kid slept through half the curves—bless.
  • Ululani’s shave ice. Fine ice. Bold flavors. I still dream about lilikoi.

What bugged me:

  • Motion sickness on the Hāna road. Ginger chews helped. I also took breaks at waterfalls to breathe.
  • Prices. Hotel rates were high, and the “resort fee” was sneaky.

One more thing: West Maui is healing from wildfires. Follow local guidance. Be kind.

Big Island: my personal favorite

If I could pick only one island for a do-it-all trip, I’d pick Big Island. It’s big—drives are long—but the payoff is huge.

What I loved:

  • Hawaiʻi Volcanoes National Park. I walked through Nāhuku (Thurston Lava Tube) with my mom. It felt like stepping into the earth’s throat. We listened to steam vents hiss. It sounded like tea kettles.
  • Two Step near Hōnaunau. I floated over coral and saw a honu (sea turtle). I kept my space. Water shoes saved my toes on the lava rock.
  • Mauna Kea Visitor Information Station at sunset. We brought jackets and hot cocoa in a thermos. When the sky went dark, the stars looked close enough to grab.
  • Kona coffee farm tour at Greenwell Farms. I learned about cherry picking and tasted fresh pour-overs. Smooth and nutty.

What bugged me:

  • Long drives. Hilo to Kona feels like a work shift. I split stays: three nights in Volcano, four in Kailua-Kona. That helped.
  • Night manta snorkel was magical, but the ocean was jumpy. I used a snug rash guard and felt fine.

Bonus: Punaluʻu black sand beach had resting turtles. We gave them space. Please don’t touch or block them.

Kauai: slow, green, and honestly, kind of perfect for calm

Kauai is lush and calm. It hums, not shouts.

What I loved:

  • Hanalei Bay at sunset. I walked the pier, and the mountains looked painted. I ate poke from the Foodland deli and watched surfers thread the last light.
  • Waimea Canyon. It’s called the Grand Canyon of the Pacific. I took short trails with my toddler and carried him back in a soft carrier when he wanted snacks.
  • Nā Pali Coast boat tour from Port Allen. I took ginger early and wore a windbreaker. Sea caves, dolphins, and a lot of “wow.”

What bugged me:

  • Chickens. Cute at first. At 5 a.m., not so much.
  • North Shore can close when it rains. I booked a Haʻena State Park shuttle day and kept plans loose.

Lanai and Molokai: the quiet islands

Lanai:

  • I took the ferry from Maui and made it a day trip. Hulopoʻe Bay had clear, calm water. Tide pools were little worlds. I rented a Jeep and went to Garden of the Gods. Red dirt went everywhere. I still found dust on my camera a week later.
  • It’s pricey to stay the night. Food is limited, but calm feels rich.

Molokai:

  • Halawa Valley hike with a local guide. He shared stories and showed us kalo (taro). We swam by a waterfall and felt small in a good way.
  • Very few hotels. No big resorts. I liked the quiet. My phone stopped being the boss.

How I choose an island now

I use a simple grid in my head:

  • Short trip (4–5 days): Oahu or Maui
  • Long trip (7+ days): Big Island or split stay
  • Want food and city plus beach: Oahu
  • Want green and peace: Kauai
  • Want lava and stars: Big Island
  • Want true low-key: Molokai or Lanai

I also skim what's trending on Popdex to catch any big events or festivals that might sway my dates.

Nerd note: I also think about ADR (average daily rate). Oahu mid-range was friendlier for my wallet than Maui.

Real trip mistakes I made (so you don’t)

  • I forgot Hanauma Bay needs a reservation. I showed up and had to come back the next day. Still worth it.
  • I brought normal sunscreen. Coral-safe only, please. I switched to mineral. No sting in my eyes either. (Hawaii’s sunscreen ban and why it matters are summed up nicely in this overview.)
  • I left the car with a beach bag in view at a scenic stop. Not smart. Now I keep the trunk clear and carry the camera on me.
  • I wore flip-flops on lava rock. My foot said ouch. Water shoes forever.

Little packing list that saved my day

  • Rash guard (sun strong, water cool)
  • Water shoes (lava and reef are sharp)
  • Light rain jacket (Kauai showers roll in fast)
  • Ginger chews or motion tabs (Hāna and boat days)
  • Reusable water bottle and a small cooler bag
  • Headlamp for sunrise hikes
  • Cash for fruit stands and shave ice

Food notes, because I care about snacks

Switching gears from poke bowls to pastries: if your itinerary has you swapping palm trees for Paris streets on the way home, peek at PlanCul Paris—the site connects travelers with locals for casual meet-ups and up-to-date tips on the best late-night cafés and croissants so you can make the most of even a quick layover.

Adding another detour idea: if your post-Hawaii route drifts south to Australia and you find yourself with a night in Tasmania’s capital, Hobart’s compact waterfront is surprisingly lively. For travelers curious about vetted