Hawaii 101 Guide

The definitive guide to choosing a Hawaiian island

By Editorial Staff

Few places satisfy the urge for a carefree tropical vacation like the islands of Hawaii. Indeed, the 50th state’s stunning beauty is no secret – nowhere else in the United States boasts the combination of white-sand beaches, lush green landscapes, pounding surf, and rich culture of these far-flung Pacific islands. But what’s less well known, especially for first-time visitors, is that there’s a lot more to the state than Oahu’s Waikiki Beach. In fact, of the eight islands in Hawaii, six are primed for tourists, each with different reasons to visit, from ecotourism and active volcanoes to beaches and nightlife.

At 2,300 miles from the contiguous United States, the Hawaiian archipelago is one of the most isolated places on earth. No wonder then that getting there is no trivial matter: From the West Coast, count on over five hours by plane to Oahu; from the East Coast, factor in a minimum of 11 hours in the air. With flight times like these, choosing the right island is imperative. The good news is that even though the islands span a seemingly huge distance – 1,500 miles in all – traveling between them has become so commonplace that, if time allows, you can definitely visit more than one on your vacation.

We’ve designed our Hawaii 101 to help you pick the island (or islands) that’s right for you. While the guide is by no means comprehensive, our overview of the six isles – Oahu, Maui, Kauai, Lanai, Big Island, and Molokai – does include a handful of can’t-miss local attractions to give you a sense of what to expect on each one, plus information on how to get there by plane or by sea. To start, we’ve proposed three basic itineraries that outline how much you can see based on your vacation time. We’ve also recommended the best islands by special interest – beach, price, golf, diving, culture, you name it – to help you further fine-tune your research. You can also get an overview of all six islands by watching our Hawaii slideshow.

HAWAII ITINERARIES
Tip: No matter how many days you plan to spend in Hawaii, you’ll need to use either Oahu or Maui as your base, as they have the most direct flights from the continental United States.

Two Weeks or More in Hawaii
Sample three different islands by air or by sea. From Maui, you can get to the Big Island and either Molokai or Lanai as your other stops; from Oahu, head north to Kauai and south to either Maui or the Big Island.

One Week in Hawaii
Explore two islands by air or by sea. We recommend pairing Oahu and Maui; Oahu and Kauai; Maui and Molokai; or Maui and the Big Island.

Long Weekend in Hawaii
Pick one island – Oahu or Maui – and stay put.

SHERMANSTRAVEL EXPERTS' FAVORITES

Most Affordable
Big Island; Oahu

Most Expensive
Maui

Best for Seclusion and Romance
Lanai; Kauai

Best for Families
Kauai; Maui

Best for the Chic Set
Kauai; Maui; Oahu

Best for the Beach
Kauai; Lanai; Maui

Best for Nature Lovers
Kauai; Molokai

Best for Culture/History
Maui; Molokai

Best for Diving/Snorkeling
Lanai; Maui; Oahu

Best for Golf
Maui

Best for Dining
Oahu

Best for Nightlife
Oahu

Best for Shopping
Maui; Oahu

Best for Surfing
Kauai; Maui; Oahu

OAHU
Affordable, Cosmopolitan, and Convenient
The third-largest Hawaiian island (after the Big Island and Maui, respectively), Oahu is the state’s most cosmopolitan destination, with a mix of skyscrapers, shops, and restaurants competing for attention with tropical rainforests and more than 100 miles of beaches. If you have time for just one island, rest assured that Oahu’s rich variety of cultural attractions and natural wonders provides a good representation of the best the islands have to offer. Lying south of Kauai and north of Molokai, the island is home to the state capital of Honolulu, world-famous Waikiki Beach, the surfing mecca that is the North Shore, and one of Hawaii’s most visited sites, Pearl Harbor, where 2,403 people died after being attacked by the Japanese on December 7, 1941 (tip: its $5 audio tour is excellent, as is the boat ride to the USS Arizona Memorial). Don’t miss the Polynesian Cultural Center, a 42-acre living museum with recreations of villages representing eight distinct Pacific island cultures. Of all the islands in Hawaii, Oahu receives the most flights from the continental US (in fact, over three times as many as its neighbors), granting it the greatest share of tourists and amenities. The result is an ideal choice if you’re looking for an affordable beach vacation with mainland amenities, but not if you’re keen to escape the masses. That said, the north side of Oahu does grant a bit of escapism, as its undulating green mountains and sapphire bays offer a quieter, more picturesque sense of the state. How to get there.

Skip to: Oahu; Maui; Kauai; Big Island; Lanai; Molokai

MAUI
A Bit of Beach, a Bit of Rainforest, a Lot of Luxury
Hawaii’s second-largest isle, Maui lies 30 miles north of the Big Island and about 70 miles southeast of Oahu; it’s also just a short distance (10 and 12 miles, respectively) from Lanai and Molokai. Whereas Oahu is the domain of beaches and surf, Maui offers a quieter blend of ecotourism and sandy shores, with dormant volcanoes, humpback whales, and a variety of black-, white-, and red-sand beaches to discover. Watching dawn break from atop the island’s 10,000-foot Haleakala Crater is one of the most memorable experiences you’ll have in Hawaii – if not your entire life. Down below, the historic whaling village of Lahaina, an absolutely delightful place chock-full of galleries, museums, shops, and restaurants, beckons (its weekly Aloha Fridays, when galleries open their doors late, creates a party atmosphere). The legendary 52-mile road to Hana, a town rife with Hawaiian folklore and traditions, is also found on Maui; expect dramatic scenery of waterfalls, lush greenery, and hairpin turns along the drive. Sights and experiences like these have tended to make Maui a more upscale destination than Oahu, with luxury resorts set on perfect beaches, and a quieter (almost nonexistent) nightlife scene, so if you’re looking for a high-end vacation that combines the best of beach and nature by day, with relaxed evenings under the stars by night, Maui is for you. How to get there.

Skip to: Oahu; Maui; Kauai; Big Island; Lanai; Molokai

KAUAI
Tailor-Made for Active Types and Nature Lovers
The northernmost island in the Hawaiian chain, verdant Kauai, 70 miles northwest of Oahu, earned the moniker Garden Island for its lush, jagged mountain range, cascading waterfalls, and abundant flora. That’s not to say the island lacks beaches; in fact, Kauai is also home to some of Hawaii’s best sands, and you could easily spend your entire vacation laid out on secluded Lumahai beach, with its lush forest backdrop, or the golden crescents of Poipu Beach, where sightings of large green sea turtles and endangered Hawaiian monk seals are commonplace. Still, Kauai has more to offer active types and nature lovers than beach bums. One of the highlights of visiting here is doing the 11-mile hike along the spectacular Na Pali Coast and camping out overnight on Kalalau Beach. Another stupendous natural sight, Waimea Canyon, is a 3,500-foot deep canyon known as the Grand Canyon of the Pacific; at 10 miles long and one mile wide, it may not be as large as the Grand Canyon, but Waimea definitely equals (and some would argue, surpasses) it in beauty. Given the action-packed days you can count on in Kauai, chances are you’ll be so worn out come nightfall, that you’ll be relieved at the island’s lack of shopping and nightlife. How to get there.

Skip to: Oahu; Maui; Kauai; Big Island; Lanai; Molokai

THE BIG ISLAND
Hawaii’s Largest and Most Diverse Island
While its official name is in fact Hawaii, the state’s largest and southernmost isle is more commonly known as the Big Island (to avoid confusion with the name of the state it occupies). And, at nearly twice the size of the all the other islands combined, the Big Island deserves its name indeed. This remote destination packs a lot into its large expanse as well: snow-capped mountains (yes, there is snow in Hawaii!), lush rainforests, the world’s most-active volcano, arid deserts, bustling towns, and fascinating beaches, including the world’s only green-sand beach, South Point. Indeed, if there’s one place that really showcases the full gamut of Hawaii’s offerings, this eponymous island may well be it. While not quite the gushing, fiery liquid of your imagination, the lava at Hawaii Volcanoes National Park is impressive nonetheless; the eruption viewing area is best visited after nightfall, when, with the help of binoculars, you’ll be able to spot lava flowing into the ocean about 4.5 miles away. The lush landscapes and tropical flora you expect of Hawaii is found in Waipio Valley, or Valley of the Kings, the home of King Kamehameha I, who conquered the islands and united them in 1810; exploring its vast beauty is best done by horseback or four-wheel-drive. In contrast, the snow-capped mountain peaks of Mauna Kea, a dormant volcano at the island’s center that ranks as the world’s tallest sea mountain – it’s taller, even, than Everest – makes for prime stargazing thanks to the high altitude, clear air, and utter darkness. How to get there.

Skip to: Oahu; Maui; Kauai; Big Island; Lanai; Molokai

LANAI
Far-Flung and Luxurious Outpost
With two luxury resorts, two championship golf courses, and an off-the-beaten path feel, tiny Lanai gives Maui (just ten miles to the east) a run for its money in both the luxury and romance departments. Often referred to as Hawaii’s private island, Lanai is about as secluded as it gets – only nearby Molokai comes close to providing the same sort of ambiance. The vibe is due, in part, to its extended ownership by the Dole Food Company, which managed pineapple plantations here from 1922 to 1985; the island’s subsequent conversion to a tourist destination has been slow, with only 30 miles of paved road, but 100 miles of hiking trails, created. Accordingly, most visitors come to Lanai to simply relax and soak up the atmosphere. Still, a few worthy activities will entice you to get off the beach chair for a day or two. You can hike, bike, or four-wheel drive the 7-mile Munro Trail to the top of Mount Lanaihale, the island’s highest peak at 3,370 feet, for spectacular ocean vistas and views of Maui, Molokai, the Big Island, and Oahu. Alternately, head to Hulopoe Bay for snorkeling and sealife watching off a protected cove bordered by an expansive gold-sand beach; watch out for acrobatic spinner dolphins in the summer months and humpback whales during their annual winter migration. Teeing off at one or both of the Four Seasons-owned golf courses is a must for any golfer; the Jack Nicklaus-designed Challenge at Manele is built on lava outcrops and uses the Pacific as a water hazard on three holes while the Greg Norman-designed Experience at Koele offers stunning mountain and ocean views. How to get there.

Skip to: Oahu; Maui; Kauai; Big Island; Lanai; Molokai

MOLOKAI
Historic Atoll Rife with Local Charm
Despite its location smack dab in the middle of two tremendously popular islands (Oahu to the north and Maui to the south) Molokai ranks among Hawaii’s least-visited destinations. It’s certainly not for lack of beauty, beaches, or history, which Molokai has in spades, but because it lacks the tourist infrastructure found elsewhere in the state – in fact, there isn’t a single stoplight on the island. The result is a rare Hawaiian experience for the intrepid traveler as Molokai is not only the birthplace of hula, it’s also home to more native Hawaiians per capita than any of the other islands, allowing visitors to experience the kama`aina (island resident) way of life. Among its other pluses, Molokai’s relative lack of visitors means you’ll never feel crowded on the beach, and it’s here that you’ll find Hawaii’s longest stretch of white sand, the three-mile Papohaku Beach Park. Away from the water, you can take a scenic mule ride along the world’s highest sea cliffs, in Kalaupapa National Historic Park, or embark on various guided hikes through the Halawa Valley that focus on history, temples, or nature. How to get there.

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