Your guide to the perfect weekend on Oʻahu, Hawaii

Oʻahu truly lives up to its nickname, the Gathering Place – it’s the Hawaiian island that has it all.

Here, you’ll find vibrant restaurants, golden beaches, luxurious resorts, historical landmarks, walkable neighborhoods, chic boutiques, and hiking trails offering stunning panoramic views.

Having grown up on this island, Oʻahu is more than just home to me. It’s where I rode my first wave, discovered my love for hiking, and where I long to return after my travels. It blends the excitement of urban life with the relaxed island atmosphere of sun-soaked beaches, lush mountains, and mai tais by the pool.

A long weekend might be just a taste – but it’s a great start. Here are some quick tips to help you plan your adventure:

• Best time to arrive: Arriving on a Thursday morning is ideal, giving you a full day to relax and prepare for a long 3-day weekend.

• Airport transportation: Renting a car at the airport is recommended for exploring the entire island. While the public bus system is convenient with many stops across Oʻahu, a rental car is quicker. Rideshare options are also available, with an average fare of $30 from the airport to Waikiki (approximately 9 miles).

• Getting around: The city bus covers the island, stopping at many popular attractions. The Waikiki Trolley has limited routes, reaching as far as Sea Life Park, about 15 miles from Waikiki. Honolulu also has a bikeshare program, but to fully explore Oʻahu, a rental car is your best bet.

• Accommodation options: Oʻahu offers a wide variety of places to stay, from the budget-friendly Hotel Renew in Waikiki to the luxurious Four Seasons Resort Oʻahu in Ko Olina. It’s the only island with a Disney-themed hotel (also in Ko Olina), featuring water slides and character breakfasts.

• What to bring: Pack casual beach attire, a warm layer just in case, sturdy shoes for walking and hiking, something nice for dinners, swimwear, flip flops (locally called slippers), and reef-safe sunscreen.

Looking to enjoy the beach? Check out our guide to the best spots in Hawaii

Friday

Morning: If you're based in Waikiki, start your day early. Grab a bullet coffee or an acai bowl at Sunrise Shack, a charming café from the North Shore that’s popular with surfers and located in the Outrigger Waikiki Beach Resort. For a more casual breakfast, check out Heavenly Island Lifestyle Waikiki, known for its brunch options ranging from sweet bread French toast topped with local honey and fruits to a zesty tomato shakshuka. Morning is the perfect time to stroll along Waikiki Beach and watch surfers catch the early waves.

How to spend the day: Waikiki is the birthplace of surfing and the ideal spot to learn. Sign up for a 75-minute lesson with the locally owned Waikīkī Beach Services and enjoy the friendly waves where renowned Native Hawaiian Olympians Duke Kahanamoku and Carissa Moore learned to surf. Alternatively, experience outrigger canoe surfing, a unique cultural activity exclusive to this island.

My favorite lunch spot post-surf is Rainbow Drive-In on Kapahulu Ave. A beloved local eatery for over 60 years, it offers hearty plate lunches and slush floats that are a must-try. For something lighter, sample an ahi poke bowl from ʻOno Seafood. Don’t miss the boiled peanuts – they’re a local delicacy.

Dinner: Enjoy handcrafted cocktails at sunset at Hau Tree, the oceanfront restaurant at the renovated Kaimana Beach Hotel. Opt for a selection of small plates or indulge in the homemade pasta or fresh fish entrées. If you're up for a short trip from Waikiki, Chinatown, about 4 miles west, is home to some of the island's finest restaurants, including Fête Hawaiʻi, a trendy bistro offering cocktails and dishes that blend French, Italian, Korean, and Hawaiian flavors. Chef-owner Robynne Maii made history as the first female chef from Hawaii to win the prestigious James Beard Award in 2022. My favorites are the Chaz burger, local-style carbonara, and the Rocky Road to Hana ice cream. Reservations are a must.

After dark: Oʻahu boasts a vibrant nightlife scene, especially in Waikiki. Check out Blue Note Hawaii, located in the Outrigger Waikīkī Beach Resort. This intimate venue, with just 326 seats, features a full-service restaurant and bar, showcasing a variety of musical acts and comedy shows, from LeeAnn Rimes to Rob Schneider. Halekūlani’s House Without a Key offers traditional hula performances and live Hawaiian music until 10pm.

Saturday

Morning: Kick off your day with an early 30-mile drive to the North Shore via Kamehameha Highway (head east toward Kahuku). This journey is part of the charm, as the two-lane highway hugs the coastline, weaving through quaint towns, roadside farm stands, and stretches of untouched beaches. Make a stop at the family-owned Kaya’s Store in Hauʻula for a Spam musubi (rice block topped with fried Spam and wrapped in nori) and butter mochi, or enjoy a slice of chocolate-haupia (coconut) pie at Ted’s Bakery near Sunset Beach.

How to spend the day: If you're visiting Oʻahu during the winter months, you'll likely be treated to the thrilling sights of massive waves. Beaches are alive with surfers and onlookers eager to witness the winter surf. During the rest of the year, this coastline is much more serene. Laniakea Beach is a favored spot to see honu, or Hawaiian green sea turtles, soaking up the sun (just remember to keep at least 10ft away on both land and in the water). Alternatively, grab a snorkel from a nearby surf shop and explore Shark’s Cove, known for its natural rocky formations that shelter tide pools teeming with over 70 species of fish (best visited in summer when the ocean is calm). Don’t miss out on garlicky shrimp scampi from Giovanni’s Shrimp Truck or stop by the roadside cafe at Kahuku Farms for a smoothie, farm pizza, or acai bowl made with locally grown ingredients.

Dinner: There’s nothing quite like dining al fresco—especially when you’re enjoying farm-to-table creations by James Beard Award-winning chef Roy Yamaguchi. His restaurant, Roy’s Beach House at the newly renovated Turtle Bay Resort, boasts breathtaking ocean vistas and a menu filled with innovative sushi rolls, fresh seafood, and his renowned molten chocolate cake. If you're visiting on a Wednesday, don't miss the hotel's Paniolo Lūʻau, which is definitely worth experiencing.

Enjoy hiking? Check out our guide to the best trails in Hawaii

Sunday

Morning: Start your day by watching the sunrise from the summit of the Kaʻiwa Ridge Trail, commonly known as the Lanikai Pillbox Trail. This 1-mile, predominantly uphill hike leads to two concrete pillboxes constructed in early 1943. I usually park at Kailua Beach and walk to the trailhead, which is nestled in a residential area. You won't find a better vantage point of the iconic Nā Mokulua (“twin islands”) off Lanikai Beach. Afterward, head to Over Easy, a charming family-run restaurant that offers crispy pancakes, French toast crusted with Cinnamon Toast Crunch, and my personal favorite: potato ‘n’ eggs.

How to spend the day: I often stroll along Kailua Beach, which spans 2.5 miles and offers views of Popoiʻa Island (also known as Flat Island) and the Mokulua Islands. Whether you choose to take a leisurely walk or simply sit back and soak in the scene—kiteboarders, canoe paddlers, swimmers, and dog walkers abound—there’s plenty to enjoy. Swing by Kalapawai Market for a quick snack, sandwich, or fish taco. This coastal community is highly walkable, with delightful boutiques, trendy coffee shops, and popular restaurants all within reach. Treat yourself to shave ice at Island Snow Hawaiʻi, which serves all-natural syrups in island flavors like lilikoʻi (passion fruit), guava, Kona coffee, and dragon fruit. Don't forget to browse through Bookends, a beloved new and used bookstore where you can snag beach (or airplane) reads for under $5.

If it’s time to wrap up your Oʻahu getaway, make the 30-minute drive from Kailua to the airport. But if you can stay longer, explore the rest of this beach town—there’s so much more to discover on Oʻahu.

Continue planning your Hawaiian adventure:

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