A Weekend Guide to 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, and where I always want to return 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.
Planning Your Trip to Oʻahu
A long weekend may not be enough – but it’s a start. First, here are some quick tips to help you plan:
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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.
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How to get from the airport: It’s best to rent a car at the airport. A rental car is necessary to explore the entire island, although the public bus system is great with stops all over Oʻahu. Rideshare options are also available, with an average cost from the airport to Waikiki (about 9 miles) around $30.
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Getting around: The city bus covers routes all over the island, stopping at popular visitor attractions. The Waikiki Trolley offers limited routes, and the city has a bikeshare program available in urban Honolulu. However, to fully experience all of Oʻahu, renting a car is recommended.
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Where to stay: Oʻahu offers the most diverse range of accommodations, from budget-friendly options to luxury resorts. It’s also the only island with a Disney-themed hotel, located in Ko Olina, complete with water slides and character-filled breakfast experiences.
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What to pack: Bring casual beachwear, something warm just in case, shoes for walking and hiking, something dressy for dinner, swimwear, flip flops (referred to as slippers), and reef-safe sunscreen.
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 café started by surfers. If you’re looking for a casual breakfast, head to Heavenly Island Lifestyle Waikiki, which offers a variety of brunch dishes. Morning is the best time to walk along Waikiki Beach and watch surfers catch early waves.
How to spend the day: Waikiki is the birthplace of surfing and is the best place on the island to learn the sport. A friendly intro to surfing in local waves is a must. Alternatively, jump in an outrigger canoe to experience an essential part of Hawaiʻi’s rich culture.
My go-to, post-surf lunch spot is Rainbow Drive-In, which serves hearty plate lunches and slush floats. For something lighter, an ahi poke bowl from nearby ʻOno Seafood is recommended. Don’t forget to try the boiled peanuts – a local specialty!
Dinner: Sip on handcrafted cocktails at sunset at Hau Tree, the oceanfront restaurant at the revamped Kaimana Beach Hotel. Share small plates or indulge in housemade pasta or fresh fish entrées. If you venture away from Waikiki, Chinatown boasts some of the island’s best restaurants with a variety of culinary options. Reservations are recommended for the most popular spots.
After dark: Oʻahu boasts a vibrant nightlife, with live music prevalent in Waikiki. Blue Note Hawaii is an intimate venue that hosts an array of musical talents. For a taste of traditional hula and live Hawaiian music until 10pm, check out Halekūlani’s House Without a Key.
Saturday
Morning: Begin your day with an early drive to the North Shore along Kamehameha Highway. The scenic route passes rural towns and picturesque beaches. Stop at local businesses for a snack or a treat along the way, such as Spam musubi or pie from Ted’s Bakery.
How to spend the day: If your visit falls during winter months, expect to witness breathtaking big waves and surfers showing off their skills. During summer, the beaches are more tranquil, ideal for relaxation and snorkeling. Laniakea Beach offers chances to see Hawaiian green sea turtles basking, while Shark’s Cove is popular for snorkeling.
Dinner: Experience farm-to-table dining at Roy’s Beach House, where you can enjoy spectacular ocean views and dishes crafted by a James Beard Award-winning chef. The menu includes inventive sushi rolls and signature desserts.
Sunday
Morning: Catch the sunrise at the top of the Kaʻiwa Ridge Trail, also known as the Lanikai Pillbox Trail. Enjoy the breathtaking views of the Nā Mokulua islands before heading to Over Easy for a delightful breakfast featuring pancakes and a variety of dishes.
How to spend the day: Stroll along Kailua Beach, which stretches for 2.5 miles, or enjoy watching local activities such as kiteboarding and canoe paddling. You’ll find plenty of shops and eateries, perfect for sampling local flavors, like shave ice at Island Snow Hawaiʻi.
Conclusion
If your time in Oʻahu must come to an end, make the brief drive back to the airport. However, if you’re able to extend your stay, delve into the many more offerings this beautiful island provides.
