Hawaii’s largest city looks like any other big metropolitan center with tall buildings. In fact, some cynics refer to it as “Los Angeles West.” But within Honolulu’s boundaries, you’ll find rainforests, deep canyons, valleys, waterfalls, a nearly mile-high mountain range, coral reefs, and gold-sand beaches. The city proper—where most of Honolulu’s residents live—is approximately 12 miles wide and 26 miles long, running east-west roughly between Diamond Head and Pearl Harbor. Within the city are seven hills laced by seven streams that run to Mamala Bay.

Finding Your Way Around, Oahu-Style

Mainlanders sometimes find the directions given by locals a bit confusing. Seldom will you hear the terms east, west, north, and south; instead, islanders refer to directions as either makai (ma-kae), meaning toward the sea, or mauka (mow-kah), toward the mountains. In Honolulu, people use Diamond Head as a direction meaning to the east (in the direction of the world-famous crater called Diamond Head), and Ewa as a direction meaning to the west (toward the town called Ewa, on the other side of Pearl Harbor).
So if you ask a local for directions, this is what you’re likely to hear: “Drive 2 blocks makai (toward the sea), and then turn Diamond Head (east) at the stoplight. Go 1 block, and turn mauka (toward the mountains). It’s on the ʻEwa (western) side of the street.”
A plethora of neighborhoods surrounds the central area. These areas are generally quieter and more residential than Waikiki, but they’re still within minutes of beaches, shopping, and all the activities Oahu has to offer.

Waikiki ★★—Waikiki is changing almost daily. There’s now a Ritz Carlton, and the nearly-new International Marketplace anchored by Saks Fifth Avenue. It’s a sign of Waikiki’s transformation: faded Polynesian kitsch giving way to luxury retailers and residences. Still, Waikiki tenaciously hangs on to its character: Explore just 1 block mauka of Kalakaua Ave., and you’ll find hip boutique hotels, hidden hole-in-the-wall eateries, and walk-up apartments and nondescript condos where locals still live.

When King Kalakaua played in Waikiki, it was “a hamlet of plain cottages . . . its excitements caused by the activity of insect tribes and the occasional fall of a coconut.” The Merrie Monarch, who gave his name to Waikiki’s main street, would love the scene today. Some 5 million tourists visit Oahu every year, and 9 out of 10 of them stay in Waikiki. This urban beach is where all the action is; it’s backed by 175 high-rise hotels with more than 33,000 guest rooms and hundreds of bars and restaurants, all in a 1 1/2-square-mile beach zone. Waikiki means honeymooners and sun seekers, bikinis and bare buns, an around-the-clock beach party every day of the year. Staying in Waikiki puts you in the heart of it all, but be aware that this on-the-go place has traffic noise 24 hours a day—and it’s almost always crowded.

Ala Moana ★★—A great beach as well as Hawaii’s largest shopping mall, Ala Moana is the retail and transportation heart of Honolulu, a place where you can both shop and suntan in one afternoon. All bus routes lead to the open-air Ala Moana Center, across the street from Ala Moana Beach Park ★★. The shopping center is one of Hawaii’s most visited destinations for its collection of luxury brands (such as Louis Vuitton and Chanel) and Hawaii-based stores (from Tori Richard to Town & Country Surf). 

Kakaako ★—This is Honolulu’s most rapidly developing neighborhood—a primarily industrial area giving way to new condo buildings, from workforce housing to the island’s most expensive penthouses. Sprouting up among the new construction are lively hubs of boutiques and restaurants, including Ward Village and Salt

Downtown and Chinatown ★★—Here you’ll find historic Honolulu, including Iolani Palace, the official residence of Hawaii’s kings and queens; its business center housed in high rises; and the Capitol District, all jammed in about 1 square mile. On the waterfront stands the iconic 1926 Aloha Tower.

On the edge of downtown is the Chinatown Historic District, one of the oldest Chinatowns in America and still one of Honolulu’s liveliest neighborhoods, a nonstop pageant of people, sights, sounds, smells, and tastes, though not all Chinese. Southeast Asians, including many Vietnamese, share the old storefronts, as do Honolulu’s oldest bar (the divey Smith’s Union Bar) and some of the city’s hippest clubs and chic-est boutiques.

Go in the morning, when everyone shops for fresh goods such as mangoes (when in season), live fish (sometimes of the same varieties you saw while snorkeling), fresh tofu, and hogs’ heads.

Manoa Valley ★—This verdant valley above Waikiki, blessed by frequent rain showers, was the site of the first sugar and coffee plantations in Hawaii. It still has vintage kamaaina (native-born) homes, one of Hawaii’s premier botanical gardens (Lyon Arboretum ★), the ever-gushing Mānoa Falls, and the 320-acre University of Hawaii campus, where 50,000 students hit the books when they’re not on the beach.

To the East: Kahala—Except for the estates of millionaires and the luxurious Kahala Hotel & Resort ★★★, there’s little out this way that’s of interest to visitors.

East Oahu

Beyond Kahala lies East Honolulu and suburban bedroom communities such as Aina Haina, Niu Valley, and Hawaii Kai, among others, all linked by the Kalanianaole Highway and loaded with homes, condos, fast-food joints, and strip malls. It looks like Southern California on a good day. You’ll drive through here if you take the longer, scenic route to Kailua. Some reasons to stop along the way: to snorkel at Hanauma Bay ★★ or watch daredevil body surfers and boogie boarders at Sandy Beach ★; or to just enjoy the natural splendor of the lovely coastline, which might include a hike to Makapuu Lighthouse ★★.

The Windward Coast

The windward side is on the opposite side of the island from Waikiki. On this coast, trade winds blow cooling breezes over gorgeous beaches; rain squalls spawn lush, tropical vegetation; and the fluted Koolau mountain range preens in the background. B&Bs, ranging from oceanfront estates to tiny cottages on quiet residential streets, are everywhere. Vacations here are spent enjoying ocean activities and exploring the surrounding areas. Waikiki is a 20-minute drive away.

Kailua ★★★—The biggest little beach town in Hawaii, Kailua sits on a beautiful bay with two of Hawaii’s best beaches. In the past few years, the town has seen some redevelopment, with a new Target, Whole Foods, condos, and newer, bigger digs for old favorite shops and restaurants. But in between, there are still funky low-rise clusters of timeworn shops and homes. Kailua has become the B&B capital of Hawaii; it’s an affordable alternative to Waikiki, with rooms and vacation rentals starting at $100 a day. With the prevailing trade winds whipping up a cooling breeze, Kailua attracts windsurfers from around the world. On calmer days, kayaking or stand-up paddling to the Mokulua Islands off the coast is a favorite adventure.

Kaneohe Bay ★—Helter-skelter suburbia sprawls around the edges of Kaneohe, one of the most scenic bays in the Pacific. After you clear the trafficky maze of town, Oahu returns to its more natural state. This great bay beckons you to get out on the water; you can depart from He‘eia Boat Harbor on snorkel or fishing charters. From here, you’ll have a panoramic view of the Koolau Range.

Kualoa/Laie ★[em]The upper-northeast shore is one of Oahu’s most sacred places, an early Hawaiian landing spot where kings dipped their sails and ghosts still march in the night. Sheer cliffs stab the reef-fringed seacoast, while old fish ponds are tucked along the two-lane coast road that winds past empty gold-sand beaches around beautiful Kahana Bay. Thousands “explore” the South Pacific at the Polynesian Cultural Center in Laie, a Mormon settlement with a temple and university.

The North Shore ★★★—For locals, Oahu is often divided into “town” and “country”—town being urban Honolulu, and country referring to the North Shore. This coast yields expansive, beautiful beaches for swimming and snorkeling in the summer and world-class waves for surfing in the winter. Laid-back Haleiwa ★★ is the social hub of the North Shore, with its casual restaurants, surf shops, and clothing boutiques. Vacation rentals are the most common accommodations, but there’s also the first-class Turtle Bay Resort ★★. Be forewarned: It’s a long trip—nearly an hour’s drive—to Honolulu and Waikiki, and even longer during the surf season, when tourists and wave-seekers can jam up the roads.

Central Oahu

Flanked by the Koolau and Waianae mountain ranges, the 1,000-foot-high Leilehua Plateau runs up and down the center of Oahu. Once covered with sandalwood forests (hacked down for the China trade) and later the sugarcane and pineapple backbone of Hawaii, Central Oahu is now trying to find a middle ground between farms and suburbia, from diversified agriculture in Kunia to the planned community in Mililani.  Let your eye wander west to the Waianae Range and Mount Kaala, at 4,020 feet the highest summit on Oahu; up there in the misty rainforest, native birds thrive in the hummocky bog. In 1914, the U.S. Army pitched a tent camp on the plain; author James Jones would later call Schofield Barracks “the most beautiful army post in the world.” Hollywood filmed Jones’s From Here to Eternity here.

Leeward Oahu: The Waianae Coast

The west coast of Oahu is a hot and dry place of dramatic beauty: white-sand beaches bordering the deep-blue ocean, steep verdant green cliffs, and miles of Mother Nature’s wildness. Tourist services are concentrated in Ko Olina Resort, which has a Disney hotel and a Four Seasons (new in 2016), pricey resort restaurants, golf course, marina, and a wedding chapel, should you want to get hitched. This side of Oahu is less visited—though that could change as Ko Olina lures visitors from Waikiki—except by surfers bound for Makaha Beach ★★ and those coming to see needle-nose Kaena Point ★ (the island’s westernmost outpost), which has a coastal wilderness park.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.