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Plan Your Trip to Oahu, Hawaii

Waikiki beach

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When to go

Visitors flock to the island all year long, but the busiest (and most expensive) time to visit is during the winter holidays, with summer months a close second. The first few months of the year offer smaller crowds, slightly cooler temperatures, and whales, although rain is more likely during this time and ocean conditions tend to be more erratic. Spring is a good time to visit, but try to avoid the spring-break crowds. Fall months typically offer better deals and fewer visitors (September and October are great months, for example) but remember that the rainy season begins in November. While average temperatures in Hawaii only vary slightly — highs in the high 80s in summer and in the low 80s and high 70s the rest of the year — the presence of trade winds makes the difference between balmy and sticky.

Because of the distance from the mainland, Hawaii visitors prefer to settle in for a week or two — or even longer. For those not constrained by work and school schedules, timing a visit around long weekends like Thanksgiving, Labor Day and Memorial Day can offer decent deals and fewer visitors sharing your slice of the beach. On such occasions, you’re likely to happen upon a backyard or beach luau, or a holiday pot luck with local families enjoying a day off.

Ways to save: For the best prices, book during low-season dates. Don’t overlook the combined fly-and-stay deals offered by many airlines, but check them carefully to be sure you can’t do better on your own. 

Where to stay

Oahu may be small — a scant 30 miles wide by 44 miles long — but it offers several distinct areas with unique offerings and appeal to visitors. Urban Honolulu, the state capital on the southeastern coast that includes Waikiki Beach, the downtown business district and lively neighborhoods like Chinatown and Kakaako, is steeped in surf, sand, dining and culture. On the island’s windward (east) side, gorgeous beaches define the region’s sleepy towns, with just enough shopping and dining to keep you from spending all day in the water. Surfing is the North Shore’s claim to fame, with iconic beaches known for massive waves (in winter) and epic views, as well as a smattering of food trucks and local hangouts. The Leeward (west) Coast is home to Ko Olina, a self-contained resort and golf community, plus a long stretch of beaches and rural communities that’s home to some of the most authentic native Hawaiian experiences on the island.  

Oahu’s 300 hotels — mostly clustered in Waikiki with some along the North Shore and Leeward Coast — offer 58,000 rooms ranging from budget to pure luxury. Add timeshares and rental properties like Airbnb and VRBO to the mix, and simply deciding where to lay your head might be the decision most deserving of a mai tai upon arrival.

The historic Royal Hawaiian and Moana Surfrider hotels were the first two properties built along the 2.5-mile stretch of sandy beach in Waikiki, and they remain iconic as ever today among the myriad newer luxury, beachfront hotels. Living large comes at a high price in Hawaii, however, with rates starting from the mid $300s to $700-plus per night for a garden or restricted view.

Less pricey Waikiki options include the Hilton Hawaiian Village, a wandering complex where Elvis Presley filmed Blue Hawaii, with 18 restaurants, cafes and bars, a spa, a children’s program for the grandkids, entertainment, hula performances, fire dancers and a Friday-night fireworks show. (It has many ADA-compliant rooms and provides closed-captioned TV for the hearing impaired.) Or check out the Sheraton Princess Kaiulani (directly across from the Moana Surfrider) and the several Outrigger hotels and condos. You can find rooms for under $200 a night at the DoubleTree by Hilton Hotel Alana, the funky Surfjack Hotel, the Holiday Inn Resort Waikiki Beachcomber and the Courtyard by Marriott Waikiki Beach.

If your ideal vacation includes a little golf surrounded by pool and beach days, Oahu’s North Shore offers Turtle Bay Resort as well as the budget-minded Courtyard by Marriott Oahu North Shore. North Shore locals live by the phrase, “keep the country country,” so don’t expect the nightlife and buzz of Waikiki. On the western side of the island, golf, spas, fine dining, luxury and Disney-style pampering can be found in the resorts of Ko Olina, including a newly completed Four Seasons, the Disney resort Aulani (with a complimentary kids club for grandkids) and condo villas boasting up to three bedrooms. 

Vacation rentals can be found all over the island, from the North Shore’s surf town, Haleiwa, to Kailuaon the east coast, a blooming beach town boasting a three-mile stretch of sandy beach considered one of the world’s best. Airbnb, HomeAway and VRBO offer hundreds of excellent selections, from small cottages to luxury homes — many perfect for a big ohana, or extended family. Make sure you know what’s in the area near the property; sometimes that great price may anchor you a long way from the beaches, markets, restaurants and places of interest. Your best bet is to stick with known areas like Ko Olina, Kailua, Waikiki and Haleiwa. 

Ways to save: Always ask about age-related discounts (some start at 50 years old), extended-stay deals (especially with vacation rentals), fifth-night-free promotions in select hotels, and package specials.

How to get there 

Oahu is a little over 2,500 miles from the U.S. West Coast. There are only two ways to get there: air or sea. Twenty-three U.S. and international airlines serve Honolulu International Airport (HNL), which sees an average of 20 million visitors each year and is located nine miles from Waikiki. Honolulu is also a favorite stop on many cruise itineraries, both those within Hawaii and those headed to Asia, Australia and New Zealand. Many ships dock overnight, allowing time to explore the island’s beaches and nightlife. There are several options for getting from HNL or the port to your destination. Cabs are readily available at the airport, costing around $30 (or more) to Waikiki, and twice that or more to windward Oahu and the North Shore. In late 2017, the state started allowing airport service by Uber and Lyft at two designated locations, which are reliably cheaper than traditional taxis. City bus service is also available at the airport. (Be aware, however, that the city bus doesn’t have storage space for luggage.)

Ways to save: Some hotels offer courtesy shuttles, so check at the time of booking. But numerous operators, including Go Hawaii Shuttle, Ohana Transit, Roberts Hawaii Airport Shuttle and the wheelchair-accessible Speedi Shuttle, offer shared transportation to Waikiki and other areas starting at $16 per person.

Activities to arrange before you go

Frequent visitors know the secret — the best of Oahu is discovered after you land. No need to pack your days with bookings and activities before you get a lei around your neck. Most activities can be booked once you arrive, particularly if you’re flexible.

However, some special places require advance booking due to limited capacity: the famed Doris Duke Estate, Shangri La, a museum of Islamic art, culture and design; the Iolani Palace, the only royal palace in the United States and a must-visit for history lovers; and Pearl Harbor, where you must reserve your spot for the Arizona Memorial tour ahead of time (tickets are available up to eight weeks in advance). In addition, tours on the 4,000-acre Kualoa Ranch should also be booked ahead due to popularity.

If you plan to rent a car, be sure to reserve one ahead of time, since companies often run out of various options and occasionally even run out of cars.  

If you’re looking to renew your vows (or even tie the knot), you’ll want to plan well before the date. Oahu records close to 1,000 weddings per month. It’s one of the most popular destination-wedding locations in the world. Couples who opt for a simpler, feet-in-the-sand-at-sunset celebration still require a bit of advance planning for license acquisition, securing an officiant and so on. Add vow renewals to those wedding numbers and that makes for a lot of brides lining up along the beaches.

What to pack

Not much! Remember the casual aloha attire of the casts Hawaii Five-0 (both the original and the 21st-century remake)? It’s what’s happening in Hawaii, no matter the season. Toss in shorts, T-shirts, flip-flops (or slippahs, as they’re called in the islands), a couple pairs of long pants and you’re set. Don’t forget comfortable shoes for walking and hiking, a light jacket or sweater for the cool ocean breezes, a rain jacket or poncho for passing showers, and plenty of sunscreen. Women usually wear skirts or sundresses for dinner, and guys fit right in with a collared shirt, slacks and a pair of loafers.  

Safety

Violent crime on Oahu is relatively rare, averaging 2.5 incidents per 1,000 people — significantly lower than the national rate of 4 per 1,000 people (2022 report data). Larceny-theft is the most common property crime in Hawaii (71 percent of all property crime), so caution is the watchword. Take care to keep your valuables close by. Don’t leave things unattended on the beach or in your rental car (including the trunk), even when parked in seemingly safe, busy areas like beach parks and trailheads (these are, in fact, the most common areas where break-ins occur).

Oahu’s trails, beaches and natural attractions can pose danger if not respected. Know your limits and come adequately prepared with water, sunscreen, cellphone, proper footwear, rain jacket or poncho, and other supplies. On the beach, always swim and snorkel with a buddy, and don’t get in the water if there are warning signs posted. Look up and down the beach, and determine if locals are getting in the water. If they aren’t, chances are they know something you don’t, so ask them if it’s safe. Of course, it’s always best to swim at beaches with lifeguards. Never turn your back to the ocean, and steer clear of tide pools, which can pose great danger. Follow the simple rule: When in doubt, don’t go out. Check Hawaii Beach Safety for real-time conditions and warnings.

When hiking, research the trail, its difficulty and whether it’s sanctioned for hiking. Before you go out to find that gorgeous vista you saw posted on social media, do your homework! Oahu’s hikes range from mild footpaths to heart-pounding, death-defying summits. People often underestimate the difficulty of trails, and find themselves in need of rescue when things go awry. Common sense, preparedness and an honest evaluation of your ability are always your best guides. Ask about the trails in advance — how steep they are, what the footing is like, whether they are shaded or open to the sun.

Editor's note: This article was originally published on February 23, 2018. It's been updated to reflect new information.

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