Kaua'i is the oldest in the Hawaiian island chain. As a result it is the most lush, hence the nickname “The Garden Isle.” With only 60,000 residents, this is one of the least populous islands. There are gorgeous hotels here, but not much nightlife compared to Maui or O'ahu. Most locales outside of the hotels will close by 9pm. If hotels aren’t your thing, there are a lot of vacation rentals available as well. This is an outdoor-lover’s paradise: hiking, snorkeling, kayaking, surfing, waterfalls, rivers, beaches, canyons, sea caves… it’s all here. This is the island for thrill seekers: the Na Pali coast is one of the most spectacular outdoor adventure playgrounds in the world. Kaua'i is where Hollywood comes to film Hawaii, from South Pacific and Blue Hawaii to Jurassic Park and Six Days, Seven Nights. As a result, many celebrities have exclusive vacation homes here, and AOL founder Steve Case is the second-largest land-owner on the island. When pressed, we’ll admit that this is one of our favorite islands. Car rental recommended. Airport: Lihue, direct flights from the mainland available.
Kaua'i
O'ahu
Originally named “The Gathering Place” by the Hawaiians, O'ahu is the most crowded of all the islands. Honolulu is the 11th largest city in the U.S., so expect high-rises, freeways, and traffic. On the flip side, that also means fun nightlife, world-class restaurants, and lots of shopping—including the largest open-air mall in the world. Hotels range from 5-star luxury to seedy motels. Not into crowds? Simply get out of Waikiki. You can rent a house on a different part of the island (the North Shore is a great option) and enjoy O'ahu like we do. Hiking, waterfalls, surfing, diving… O'ahu is mega-equipped to provide just about anything you could wish for in a vacation. Car rentals recommended when taking day trips outside of Waikiki. Airport: Honolulu, direct flights to and from the mainland and international destinations.
Moloka'i
Without a doubt the most tranquil and remote of all the Hawaiian islands, only small propeller planes fly to Moloka'i. It’s often referred to as the most “Hawaiian” of all the islands, and indeed it is the only island of which the population is more than 50% native Hawaiian. Nightlife is practically nonexistent and it only has a few restaurants to choose from. But Moloka'i is incredibly beautiful and peaceful—and you can ride a mule down the tallest ocean cliffs in the world. There really are only two hotels on the island, but many condos and vacation homes are available for short- or long-term rental. You can take a ferry here from Maui, or fly in from one of the outer islands (no direct flights from the mainland). With only 75,000 visitors a year, “The Friendly Isle” is the spot for those looking for serious seclusion.
Lana'i
When we were kids, James Dole (as in Dole Food Co.) owned the entire island of Lana'i, and there was nothing here but pineapple fields. Now a development company owns over 90% of the island, and three hotels cater to tourists. Two of the hotels are upscale Four Seasons Resorts, but the third is cute and very "old Hawaii." There’s only one town on the island, and only about 3,000 residents call Lana'i home. Don't expect an action-packed vacation here—Lana'i is all about winding down. Go to the beach, play golf, sit by the pool at your resort and read a book. There are not many places to eat other than at the hotels. And no need to rent a car here: everything is accessible by the vans the hotels provide to get around, and there are only 15 miles of paved roads. Take a ferry here from Maui, or fly in on a prop plane from one of the outer islands. (Note from the editors: Lana'i used to be known as “The Pineapple Isle” but it has been renamed “The Most Enticing Isle.” We think that’s cheesy marketing drivel and refuse to promote it as such.)
Maui
Parts of Maui are crowded with tourists and bustling commercial centers, but much of island is still pristine and remote. Hana is a quirky and charming area on the east side of the island, away from the crowds. The narrow, winding “Road to Hana” is famous for its scenic views and white-knuckle curves. There is a luxury hotel and spa in Hana, but the town is small and only has around 200 residents. Maui, a.k.a. “The Valley Isle,” has beautiful waterfalls with swimming holes, black and red sand beaches, hiking, and some of the best windsurfing in the world. Haleakala, a 10,000 foot mountain that translates into “House of the Sun,” is one of the best places on the planet to watch a sunrise. The adventuresome can ride bicycles all the way down the volcano. Unlike some of the other more sleepy islands, there's plenty of nightlife in Maui. Lahaina, aside from being pretty touristy, is actually a quaint, historic whaling town. Maui is a great option for people who want a little of everything Hawaii has to offer. Car rental recommended. Direct mainland flights fly into Kahului airport; interisland flights are available to all islands.
Hawai'i (The Big Island)
On the Big Island you'll find almost every climate on earth, from rain forest to tundra to deserts. At 14,000 feet, the volcanic peaks of Mauna Loa and Mauna Kea are often covered with snow during winter. Although the Big Island has the second largest population after Oahu, the sheer size of this island makes it seem one of the least populous in the state. Two main towns cater to visitors, Hilo and Kona. Hilo is on the windward side of the island and it is known for being a bit rainy. However, because of its climate it is the most lush area on the island, and a world-renowned region for growing orchids. Kona is hot and dry, and boasts some of the best diving in the islands (a night dive with manta rays is not to be missed!). Because of its scale, the Big Island can offer completely different vacations to different people: from luxury resorts with waterslides and golf courses, to horseback riding on a working ranch, to lodging on the rim of an active volcano. This is a spectacular island, one of our favorites. Car rental is a must. Flights into both Hilo and Kona are available.
