Best Island to Travel to in Hawaii: 5 Picks Compared

Oahu squeezes the state's biggest variety into the shortest distances. You can snorkel at Hanauma Bay in the morning, stand at the USS Arizona Memorial at Pearl Harbor after lunch, and watch winter surf at Waimea Bay on the North Shore before dinner. It is also the island that asks the least of you: Honolulu has the rental cars, the buses, the guided day tours and the restaurants, so a first trip doesn't collapse if one plan falls through.

The trade-off is company. This is the busiest island, Honolulu traffic is slow, and Waikiki hotels charge a premium for rooms that would be mid-range elsewhere. Base yourself in Waikiki for convenience and add two nights on the North Shore if you want the slower version.

Maui is the safest bet for a single-island week. You can catch sunrise from the Haleakala summit, drive the Road to Hana through rainforest and waterfalls, snorkel the Molokini crater, and still be on the sand at Kaanapali or Wailea by mid-afternoon. Resorts are polished, food is genuinely good, and the island is small enough that nothing feels like an expedition.

The catch is that the headline experiences are booked, not improvised: Haleakala sunrise entry, popular restaurants and the Road to Hana on a busy weekday all reward planning. Accommodation is the most expensive of the five on average. Base in South Maui for calm water and shorter drives, or West Maui for resort facilities and sunsets.

The Island of Hawaii is larger than all the other islands combined, and it behaves like a small country: dry lava fields around Kona on one side, rainforest around Hilo on the other, and Hawaii Volcanoes National Park in between, where Kilauea ranks among the most active volcanoes on earth. Add the Mauna Kea summit (four-wheel drive required, and you should acclimatise at the visitor station first), Punaluu's black sand, Kona coffee farms and manta ray night snorkelling, and you get the most varied week in the state.

The weakness is logistics. Distances are long, so a single base means hours in the car; split your stay between the Kona and Hilo sides. White-sand swimming beaches are fewer, and many shoreline entries are rocky.

Kauai is the scenery island. The fluted green cliffs of the Napali Coast, the red rock of Waimea Canyon, Hanalei Bay and the rain-soaked high ground of Mount Waialeale deliver landscapes the other islands can't match. Hikers have the Kalalau Trail — permits required, and the first section to Hanakapiai Falls is the realistic day walk — while everyone else sees the coast by boat or helicopter, because there is no road along it.

Development is low-rise and the pace is slow, which is the point. It is also the rainiest of the five, especially on the north shore in winter, and the island's lack of a coastal loop road means you commit to one side each day.

Molokai is Hawaii without the sheen: Kaunakakai's low-slung main street, the three-mile sweep of Papohaku Beach, the Halawa Valley, and the Kalaupapa peninsula, which you can only reach on a guided tour and which carries the history of the Hansen's disease settlement and Father Damien. There are no high-rise resorts and very little organised for you, which is precisely the appeal.

Come for hiking, fishing, empty sand and a pace that feels a generation behind. Don't come for nightlife, snorkelling infrastructure or a first Hawaii trip. Book your rental car and any Kalaupapa tour before you fly — inventory is small and it does sell out.