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Hawaii Island Hopping: How to Visit Two Islands in One Trip

Should you try to fit another island into your trip or stay put? Tough call. Although none of the islands are more than thirty minutes away from another by air, security hassles, transport, and check-in all swallow up precious vacation hours. If you’ve got less than a week, you might want to stay put. But if you’re considering a longer stay in Hawaii—and we hope you are—here are some ideas for ways to expand your trip.

Ideas for Side Trips from Oahu


With a week, you can give three good tour days to Oahu (Pearl Harbor, Honolulu, and one rural venture), then head to a Neighbor Island for some serious beach time and maybe an adventure or two.

“My normal vacation is a two island trip. While I not an Oahu fan, there is much to do there. My choice would be one week on the Isle of Hawii and one week Oahu. On oahu you get the meals, shopping, culture, history, some great beaches and a nightlife. On the BI you get pristine snorkeling, hiking, more hiking, great parks, gardens, and a volcano. A few nice beaches and many places to get away from the maddening crowd.” — wbpiii

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Ideas for Side Trips from the Big Island

Maui is the Big Island’s closest neighbor—on a sunny day you can see it clearly from the Kohala Coast—and the flight there is barely half an hour. For nightlife-deprived visitors, a weekend trip to check out the lively bars and restaurants on Maui might be the perfect solution. If you’re visiting in October, consider hopping to Maui for its famous Halloween party. Go, Aloha, and Hawaiian all offer island-hopping flights, usually at very low prices.

Ideas for Side Trips from Kauai

If you have a week or more on Kauai and you’ve never visited Pearl Harbor, the Arizona Memorial and U.S.S. Missouri, you may want to consider taking a day trip to Oahu. Catch the first flight out and head straight to the Arizona Memorial, or you may risk long lines and an hours-long wait.

If you want to travel to Maui to experience the Road to Hana or to the Big Island to see Volcanoes National Park, there are few convenient nonstop flights; most lay over in Honolulu, so you’ll have to plan an overnight.

Ideas for Side Trips from Maui

If you have a week or more on Maui, you may want to set aside a day or two for a trip to Molokai or Lanai. Tour operators such as Trilogy offer day-trip packages to Lanai, which include snorkeling and a van tour of the island. Ferries are available to both islands and have room for your golf clubs and mountain bike. (The Molokai channel can be rough, so avoid ferry travel on a blustery day.)

If you prefer to travel to Molokai or Lanai by air, and you’re not averse to flying on 4- to 12-seaters, your best bet is a small air taxi. Book with Pacific Wings for flights to Hana, Maui, or Kalaupapa and Molokai, as well as the main airports.

Photo credit: istock/Drew Stephens

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