How to spend the ultimate weekend on Oʻahu, Hawaii

There’s a reason why Oʻahu is nicknamed the Gathering Place – it’s the Hawaiian island that has everything.

Here you'll enjoy buzzy restaurants, golden beaches, luxe resorts, historic sites, walkable neighborhoods, trendy boutiques and hiking trails with breathtaking panoramic views.

Born and raised on the island, Oʻahu is more than just my home. It’s where I surfed my first wave, where I fell in love with hiking, where I always want to come back to after traveling elsewhere. It combines the excitement of city life with the laid-back island vibe of sunny beaches, verdant mountains and mai tais by the pool.

A long weekend may not be enough – but it’s a start. First, here are some quick tips to help you plan:

• When to arrive: Arriving on a Thursday morning is perfect. That way you’ll have a full day to rest and unwind before an extended 3-day weekend.

• How to get from the airport: It's best to rent a car at the airport. You’ll need one to explore the entire island (the public bus system is great, with stops all over Oʻahu, but it’s faster to get around in a rental car). Rideshare is available, too; the average cost from the airport to Waikiki (about 9 miles) is $30.

• Getting around: The city bus has routes all over the island, with stops at the most popular visitor attractions on Oʻahu. The Waikiki Trolley offers limited routes, the farthest to Sea Life Park, about 15 miles from Waikiki. The city’s only bikeshare program is available in urban Honolulu. To see all of Oʻahu, though, you’ll need a rental car.

• Where to stay: Of all the islands, Oʻahu has the most diverse range of accommodations, from budget-friendly Hotel Renew in Waikiki to the luxe Four Seasons Resort Oʻahu in Ko Olina on the island’s west side. It’s the only island with a Disney-themed hotel (also located in Ko Olina), complete with water slides and character-filled breakfast experiences.

• What to pack: Bring casual beachwear, something warm just in case, shoes you can walk and hike in, something dressy for dinner, swimwear, flip flops (we call them slippers) and reef-safe sunscreen.

Want to spend time on the beach? Here's our guide to the best in Hawaii

Friday

Morning: Assuming you’re staying in Waikiki, wake up and head out early. Grab a bullet coffee or acai bowl at Sunrise Shack, a cute North Shore-based cafe started by surfers with a location in the Outrigger Waikiki Beach Resort. If you’re looking for a casual breakfast, head to Heavenly Island Lifestyle Waikiki; this laid-back spot has a variety of brunch dishes, from sweet bread French toast with local honey and fruits to a spicy tomato shakshuka. Morning is the best time to walk along Waikiki Beach and watch surfers nab early waves.

How to spend the day: Waikiki is the birthplace of surfing – and it also happens to be the best place on the island to learn the sport. Book with locally owned Waikīkī Beach Services for a 75-minute lesson in the friendly waves where Native Hawaiian Olympians Duke Kahanamoku and Carissa Moore both grew up surfing. Or jump in an outrigger canoe – an important part of Hawaiʻi’s rich culture – to catch waves. This is the only place on the island where you can experience outrigger canoe surfing.

My go-to, post-surf lunch spot is Rainbow Drive-In on Kapahulu Ave. This local favorite, around for more than 60 years, serves hearty plate lunches and slush floats, which I highly recommend. For something lighter, get an ahi poke (cubed raw fish) bowl from nearby ʻOno Seafood. Try the boiled peanuts – it’s a local specialty.

Dinner: Sip on handcrafted cocktails at sunset at Hau Tree, the oceanfront restaurant at the revamped Kaimana Beach Hotel. Share a bunch of small plates or splurge on the housemade pasta or fresh fish entrées. If you want to get out of Waikiki, Chinatown – about 4 miles west – boasts some of the island’s best restaurants, including Fête Hawaiʻi, a hip bistro with great cocktails and dishes inspired by French, Italian, Korean and Hawaiʻi flavors. In 2022, chef-owner Robynne Maii was the first female chef from Hawaii to win the prestigious James Beard Award, the state’s first in nearly 20 years. I’m obsessed with the Chaz burger, local-style carbonara and the Rocky Road to Hana ice cream. Reservations are required.

After dark: Oʻahu is the only Hawaiian island with a robust nightlife, and Waikiki is a great spot to find live music. Located in the Outrigger Waikīkī Beach Resort, Blue Note Hawaii is an intimate venue – just 326 seats with a full-service restaurant and bar – that hosts a range of musical and comedy talents, from LeeAnn Rimes to Rob Schneider. Halekūlani’s House Without a Key offers traditional hula and live Hawaiian music until 10pm.

Saturday

Morning: Get an early start with a 30-mile drive to the North Shore along the Kamehameha Highway (that means heading east toward Kahuku.) The drive is part of the experience. This two-lane highway hugs the coastline, passing through rural towns, past roadside farm stands and stretches of empty beaches. Stop for a Spam musubi (block of rice with a slice of fried Spam on top, wrapped with a strip of nori)
and butter mochi at the family-run Kaya’s Store in Hauʻula or a slice of chocolate-haupia (coconut) pie at Ted’s Bakery near Sunset Beach.

How to spend the day: If you’re on Oʻahu during the winter months, you’ll likely witness the spectacle surrounding the seasonal big waves. Beaches are packed with surfers and spectators, eager to catch the winter’s monster surf. During other times of the year, though, this stretch of coastline is quieter, the beaches less crowded. Laniakea Beach is a popular stop to see honu, or Hawaiian green sea turtles, basking on the beach (you have to stay at least 10ft away from them on land and in water). Or grab a snorkel – you can rent one from a surf shop – and hit Shark’s Cove, with natural rocky outcroppings that protect tide pools home to more than 70 fish species (this is a summer activity, as ocean conditions are calm). Feast on garlicky shrimp scampi from Giovanni’s Shrimp Truck or head to the roadside cafe at the family-run Kahuku Farms for a smoothie, slice of farm pizza or acai bowl, the ingredients of which are grown on-site.

Dinner: There’s nothing better than eating outdoors — except eating farm-to-table dishes crafted by James Beard Award-winning local chef Roy Yamaguchi. His restaurant, Roy’s Beach House at the recently updated Turtle Bay Resort, offers stunning ocean views and a menu that includes inventive sushi rolls, seafood and his signature molten chocolate cake. If you’re here on a Wednesday, the hotel’s Paniolo Lūʻau is worth checking out.

Like to walk? Here's our guide to the top hiking routes in Hawaii

Sunday

Morning: Catch the sunrise at the top of the Kaʻiwa Ridge Trail, better known as the Lanikai Pillbox Trail. It’s a 1-mile, mostly uphill trek to two concrete pillboxes built in early 1943. I park at Kailua Beach and walk to the trailhead, which is tucked away in a residential neighborhood. There’s no better view of the famous Nā Mokulua (“twin islands”) off Lanikai Beach. Then head to Over Easy, a casual family-run eatery that serves crispy-edged pancakes, Cinnamon Toast Crunch-crusted French Toast and (my favorite) potato ‘n‘ eggs.

How to spend the day: I regularly walk Kailua Beach, which stretches for 2.5 miles with views of Popoiʻa Island (aka Flat Island) and the Mokulua Islands. Enjoy a nice stroll or just sit and watch the action: kiteboarders, canoe paddlers, swimmers, folks walking their dogs. Stop at Kalapawai Market for a quick snack, sandwich or fish taco. This coastal town is very walkable, with cute boutiques, hip coffee shops and trendy restaurants all nearby. Treat yourself to shave ice at Island Snow Hawaiʻi; the shop (which Hawaiʻi-born President Barack Obama frequents) boasts all-natural syrups in island flavors like lilikoʻi (passion fruit), guava, Kona coffee and dragon fruit. Then wander through the aisles of Bookends, a beloved new and used bookshop, where you can find beach (or airplane) reads for under $5.

If you must now end your Oʻahu vacation, make the 30-minute drive from Kailua to the airport. If not, explore the rest of this beach town, to see what else Oʻahu has to offer. And trust me, there’s a lot more.

Keep planning your trip to Hawaii:

Figure out the best island for your trip
Learn the best times to avoid the crowds
Check out our first-timer's guide to Hawaiʻi Volcanoes National Park