When to go
Visitors flock to the island all year long, but the winter holidays are the busiest (and most expensive) time to visit, with summer months a close second. The first few months of the year offer smaller crowds, slightly cooler temperatures and whales. Spring is also a good choice but try to avoid the spring-break crowds. Fall months typically offer better deals and fewer visitors also, but when the winds die down, the days can get warm. While average temperatures in Hawaii only vary slightly — highs in the high 80s in the late summer and fall and in the low 80s 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. If you’re lucky, you might even happen upon a backyard luau or 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 areas like Chinatown, 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 and epic views, as well as its 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 rarely visited by tourists but 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 time shares and rental properties 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 along Waikiki’s 2.5-mile stretch of sandy beach harken back to the 1940s when airmen stationed at Pearl Harbor or Hickham Air Force Base met their dates and danced under the stars on a Saturday night. For luxury with a more modern twist, the five-star Halekulani’s elegant open-air lobby and grounds surround you with luxury and understated decadence, from the lei greeting to the sharply dressed staff attentive to your every need. For something a bit edgier, the Modern Honolulu offers a sleek boutique that eschews the tiki décor for an atmosphere of hip luxury and white minimalism. History and luxury come with a price, however, with rates ranging from the mid $300s to $700-plus per night for a garden or restricted view up to $900 to $1,200 for partial and full ocean views.
Less pricey Waikiki options include the Hilton Hawaiian Village, a wandering complex where Elvis Presley filmed Blue Hawaii, with 20 restaurants 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 the tony 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 Kailua, a sleepy coastal 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 (if you don’t mind a rural setting) the North Shore.
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.Over 27 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, particularly 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 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. 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 $10, a fraction of the cost of a cab.
Activities to arrange before you go
Frequent visitors know the secret: The best of Oahu is discovered once you arrive. 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, two special places require advance booking due to limited capacity: the famed Doris Duke Estate, Shangri La, a museum of Islamic art, culture and design, and the Iolani Palace, the only royal palace in the United States and a must-visit for history lovers. In addition, tours on the 4,000-acre Kualoa nature reserve should also be booked ahead.
If you plan to rent a car, be sure to reserve it in advance since companies often run out of various options, and occasionally even run out of cars. (Unlike on the mainland, where cars can be driven across state lines when there’s a shortage, rental car companies have a set inventory, and that’s it until one is returned.)
If you’re looking to renew your vows (or even tie the knot), you’ll want to plan well in advance. Oahu records close to 1,000 weddings per month. It’s one of the most popular destination-wedding locations in the world, with both U.S. couples and those from China, Japan and other Asian countries planning elaborate ceremonies here. 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 Hawaii Five-0’s cast (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 and plenty of sunscreen. Ladies usually enjoy a skirt or sundress for dinner, and guys fit right in with a collared shirt, slacks and a pair of loafers.
Violent crime on Oahu is relatively rare and incidents of larceny-theft dropped by 34 percent in 2015 (the most recent year reported) versus 10 years prior. However, property crime in Honolulu is 25 percent higher than the national average, while violent crime is 13 percent lower. 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).Oahu’s trails, beaches and natural attractions can pose danger if not respected. Know your limits and come adequately prepared with water, sunscreen, cellphone 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. 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, finding themselves in need of rescue when things go awry. Common sense and following the lead of experienced locals is always your best guide. Ask about the trails in advance — how steep they are, what the footing is like, whether they are shaded or open to the sun.