A Guide to Hawaii’s Islands for Every Type of Traveler

PHOTO: Lanai
Courtesy Oyster.com

Hawaii attracts about 7 million visitors annually and it’s no wonder: with a beautiful natural landscape, rich culture, and vast range of activities, it is one of the most diverse destinations in the U.S. No two islands of the six-island chain are the same, and even different areas and coasts of a single island can vary drastically. This can make it difficult to choose an island for your vacation, but it also means that all kinds of travelers can find what they’re looking for — and fortunately, travel among the islands is relatively easy and stress-free. So whether you plan on island-hopping throughout your trip, or prefer to pick one island that’s best suited to your needs, our handy island guide will make planning your Hawaiian getaway a breeze.

If you want…

PHOTO: The Big Island
Courtesy Oyster.com
A little bit of everything: The Big Island

It makes sense that the largest island (larger, in fact, than all the other islands combined) would be the most diverse, and those who seek a well-rounded experience will love the Big Island. Between fiery volcanoes, cascading waterfalls, white-sand, black-sand, and even green-sand beaches, blossoming meadows and snow-capped mountains, the options are seemingly endless. Visitors can sunbathe and snorkel by day and stargaze from frigid mountaintops by night. Stay at Outrigger Fairway Villas. This clean, affordable condo property in Waikoloa Village on the Kohala Coast offers an uncommon level of privacy: It’s located inside a gated community and surrounded by a golf course. Ranch-inspired buildings house multi-room units, complete with full kitchens and washer/dryers, and property features include an attractive (if small) infinity pool and an open-air fitness room.

PHOTO: Lanai
Courtesy Oyster.com
Romance: Lanai

With not a single stoplight on the island, it really doesn’t need to be said that Lanai is a bit off of Hawaii’s beaten path, making it a perfect spot for secluded romance. For years, Lanai was just a tiny island covered by a pineapple plantation and it hasn’t changed much since — except that some of the pineapple trees have been traded in for a few high-end resorts (where celebrity couples will occasionally stay as guests). Even though its jaw-dropping natural beauty (which includes cerulean ocean and lush forests) is its best asset, visitors will also small-town coziness — which allows for a decidedly romantic feel — on this undeveloped isle. Stay at Four Seasons Resort Lanai at Manele Bay. Offering top-rated dining, a Jack Nicklaus-designed golf course, a pristine pool and spa, and exceptional service (easily some of the best in Hawaii, it includes a 24-hour concierge, numerous beach and pool attendants, and twice-daily housekeeping), this resort is a favorite among honeymooners.

PHOTO: Kauai
Courtesy Oyster.com
Adventure: Kauai

Kauai draws visitors with the wild grandeur of its lush, mountainous terrain. Its craggy shores and natural wonders are an adventure junkie’s playground; the 10-mile-long Waimea Canyon, the lava-rock seawater pool at Queen’s Bath, and the remote, towering cliffs of the Na Pali Coast are among the world’s most unique attractions, and adrenaline-spiking activities include hiking, surfing, kayaking, skydiving, and rock-climbing. Stay at Kauai Beach Resort. This private, quiet property has large rooms, gorgeous sunrises over a rugged beach, a waterslide and sand-bottom pool, and a romantic bar with live music.

PHOTO: Maui
Courtesy Oyster.com
Classic Beach Vacation: Maui

Hawaii’s second largest island, Maui arguably lives up to its boastful slogan “Maui no ka ‘oi” (“Maui is the best”). With hundreds of beachside resorts and hotels, as well as some of the most swimmable and surfable shores in the state, Maui offers the classic beach vacation experience. While there is plenty to satisfy those who like to keep active, there’s even more opportunity for leisurely pursuits such as sunbathing, golf, and spa-going. Stay at Marriott Wailea Resort. Situated on a rock between two beaches, the 22-acre, 546-room Wailea Marriott has panoramic ocean views and a serene vibe that’s missing from some of the more crowded, neighboring resorts. The hotel’s spiffy rooms, gorgeous adult-only infinity pool (where you can sip on a mai tai), reputable spa, and popular restaurant make it the best midrange option in ritzy Wailea.

PHOTO: Molokai
Courtesy Oyster.com
Culture: Molokai

Molokai is the second smallest island in the Hawaiian chain and many would argue that it feels even more secluded and untouched than Lanai. In fact, nearly half of its residents are of native Hawaiian descent, giving it its moniker “The Most Hawaiian Island.” In addition to the requisite white-sand beaches, Molokai has considerable historic charm and is rich in culture; it is home to Kalaupapa National Historical Park, a well-maintained historic seaside settlement, as well as numerous centuries-old churches, plantations, and coconut groves. While the island is beautiful and culturally rich, most choose to visit just for the day by ferry from either Maui or Lanai. Stay at The Plantation Inn. Less than a 10-minute walk from the dock where the ferry to Molokai takes off, The Plantation Inn is one of Maui’s most intimate properties, with 19 rooms and suites, a small pool, and free breakfast from the top-notch Gerard’s Restaurant.

PHOTO: Oahu
Courtesy Oyster.com
Family Time: Oahu

Oahu, and more precisely the touristy town of Waikiki, remains an obvious choice for those who want a Hawaiian vacation — sun, sand, luaus, hula – without sacrificing the creature comforts of home, which is often just what families are looking for. Complete with a mile-long stretch of shops, restaurants, and high-rise hotels (for every budget) with tons of family-friendly activities, Waikiki offers a curious blend of mainland suburban staples and local flavor. Along the coast, manicured lawns and palm trees lead to sunny white-sand beaches where children splash about in the shallow water near the shore, while surfers and paddle-borders patrol the outer waters. Stay at Hilton Hawaiian Village. The largest resort in Hawaii is a veritable village, with five towers, five pools, 20 bars and restaurants, 90 shops, direct beach access, and a separate lagoon. The crowds can get big and the lines long. But for families and other Waikiki vacationers looking for a self-contained resort with loads to do, the Hilton is a top choice.

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