On the Road Again: How to Spend Seven Days on the Hawaiian Island of Oahu

The Island of Oahu is the most populated and third-largest island in the Hawaiian Archipelago. Here’s how to make the most of your seven-day stay in “The Gathering Place.”

Day 1: Layover in Los Angeles

Unless you’re on a miserably long and hard-to-come-by non-stop flight from the east coast to Honolulu, most of your flight options will include a stop in LAX (Los Angeles International Airport). Keep in mind, if you’re checking a bag, make sure your layover is at least two hours long to increase the likelihood that your baggage is successfully loaded onto your plane to Honolulu’s Daniel K. Inouye International Airport (HNL). Once you arrive in Honolulu, you’ll want to rent a car and head to Waikiki to stay in the heart of the action. I suggest splurging on a convertible rental to make the most of your time in Oahu’s infamous traffic congestion when traveling to and from the Honolulu and Waikiki areas. Affordable self-parking in Waikiki is few and far between. In fact, most hotels only offer valet parking for a whopping average of $40 or $50 per day during your stay. Many Airbnb or Vrbo rentals in Waikiki are located in private condominium complexes, with owners providing one free assigned parking spot with their rentals. If you’re not willing to break the bank for valet parking (who could blame you?), a condo rental might be a better fit for your vacation.

Day 2: Waikiki Beach

Ease into your Oahu vacation by spending your first full day on the island relaxing on the famous Waikiki Beach. No matter where you stay in Waikiki, the beach will only be a few blocks away, making it easy to wander around the streets of  this well-known locale for a break from the sun, or to run back to your hotel room to grab more sunscreen. There are plenty of places to rent chairs, umbrellas, lockers, floats, surfboards, and paddleboards on Waikiki Beach, but be sure to note that no alcohol is allowed on beaches in Oahu. It’s also important to be mindful of your belongings while taking a dip in the ocean or walking along the shore, as Oahu has seen an increase in car break-ins and pickpocketing over the years. At night, enjoy drinking a Mai Tai with your oceanfront dinner at Duke’s Waikiki.

Day 3: Oahu’s North Shore

If you’re already feeling the pinch of crowded Waikiki, hop in your car and take a drive to Oahu’s North Shore for the day. The North Shore is notorious for its large swells and surfing, especially during the winter months, in addition to some of the island’s best food trucks. Stop by the iconic Sunrise Shack for a tropical acai bowl, or stand in line for a shrimp plate at Giovanni’s Shrimp Truck along Kamehameha Highway in the town of Haleiwa.

Day 4: Oahu’s History

Wake up early to grab a parking spot at nearby Waikiki’s Diamond Head State Monument and hike to the top of a volcanic cone for a stunning view of Waikiki. After lunch, take a brief history break and head over to the Pearl Harbor National Memorial for a vast array of WWII exhibits and memorials honoring those who lost their lives in the tragedy that took place in 1941.

Day 5: Beautiful Lanikai Beach

Snorkelers will revel in the pristine reefs, shallow waters, and sea turtles at Hanauma Bay Nature Preserve sitting east of Waikiki. After spending the morning snorkeling with sea life, drive to the windward side of the island for picturesque Lanikai Beach, known for its calm, turquoise waters. Kayak or paddleboard off-shore to Lanikai’s Mokulua Islands, the beach’s two islets making Lanikai a sight for sore eyes. However, pay attention to currents on windward beaches, as strong winds make currents stronger and blow in pesky Portuguese Man O’ War. These jellyfish-like sea creatures pack a powerful sting with their electric blue tentacles, and in rare cases, can even be fatal if a swimmer has an unlucky allergic reaction. Lifeguards post warning signs if dangerous marine life is found in the water, so be sure to heed any warnings seen on the island’s beaches before jumping in for a swim.

Day 6: Hike Koko Crater or Wiliwilinui Ridge

Spend your last full day in Oahu by increasing your heart rate on the family-friendly Koko Crater Tramway trail (1.6 miles roundtrip), or the Wiliwilinui Ridge Trail (4.7 miles roundtrip) for a more adventurous, off-the-grid hike. Remember, many regions of the Hawaiian Islands carry tropical rainforest conditions. For ridge and waterfall hikes, pay attention to the weather forecast (although conditions can and do change rapidly). If there are rain clouds in the sky, skip the hike to prevent being swept away in a deadly flash flood.

Day 7: Depart Honolulu

Most flights leaving HNL for the mainland depart later in the day. Arrange for a late checkout of your rental or hotel room so you can spend your last few hours on the island on the beach before returning your rental car to the airport and saying “Aloha” to Oahu.


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