36 Hours on Oahu: Surf, Sunsets and Serenity

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Advisor - Joelle Massari
Curated By

Joelle Massari

  • Oahu

  • Active Travel

  • Beaches

  • Hawai'i

  • Honolulu

  • Islands

Beach on a sunny day.
Curator’s statement

Oahu weaves a spellbinding tapestry of natural beauty and cultural richness, where azure waters lap against golden shores and verdant mountains beckon adventurers. Its blend of ancient traditions and modern delights creates a captivating mosaic that promises endless exploration and unforgettable moments under the Pacific sun.

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Insider knowledge

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Where to stay

Day 1: Discovering Oahu's North Shore

Beach on a sunny day.

Begin your journey early in Honolulu, starting with a captivating sunrise at Sandy's Beach. Schedule your departure to ensure arrival in plenty of time to watch the sky slowly illuminate. This serene location is a favorite among locals for its stunning morning views over the Pacific Ocean. Remember to secure your belongings due to occasional thefts in the area.

After soaking in the sunrise, venture towards Oahu's North Shore. Along the way, stop at Kaiwi State Scenic Shoreline for a picturesque coastal hike. The rugged cliffs and expansive ocean views provide a perfect introduction to the island's natural beauty.

As you continue your drive, stop at Kalapawai Market in Kailua for delightful picnic items for breakfast or brunch. Indulge in their freshly made sandwiches, smoothies and other local specialties to fuel your day.

Next, head to Lanikai Beach, renowned for its crystal-clear turquoise waters and the iconic Mokulua Islands in the distance. While parking can be limited, the tranquil ambiance and breathtaking scenery make it well worth the visit.

In the afternoon, journey to Nu'uanu Pali Lookout for sweeping panoramic views of Oahu's Windward Coast. The lookout offers a spectacular vantage point, ideal for capturing memorable photos of the island's lush landscapes.

As evening approaches, arrive in Hale'iwa on the North Shore. Treat yourself to a refreshing Matsumoto Shave Ice, a local favorite that's perfect for cooling off after a day of exploration.

Depending on your timing and interests, consider visiting Shark's Cove for snorkeling or Sunset Beach for a leisurely stroll along the shoreline. Both spots offer unique experiences and stunning views of Oahu's renowned North Shore.

Conclude your day with a relaxing dinner at one of Hale'iwa's charming restaurants, such as Kua'Aina Sandwich Shop or Giovanni's Shrimp Truck, where you can savor the flavors of Hawai'i in a laidback setting. After dinner, reflect on your day's adventures as you return to Honolulu for a well-deserved rest.

Day 2: Exploring Waikiki's Hidden Gems

Filled malasada donuts in a cardboard box on a blue table.

Begin your second day in Waikiki by renting bicycles and exploring the vibrant stretch along Waikiki Beach. This iconic area is dotted with shops, cafes and beautiful oceanfront views, perfect for a morning of leisurely exploration. After riding bikes, go to Leonard's Bakery for scrumptious malasadas.

Afterwards, head to Duke Kahanamoku Beach for a surf lesson led by a local instructor. Whether you're a novice or experienced, the beach's gentle waves and welcoming atmosphere provide an ideal setting to learn or refine your surfing skills.

For lunch, indulge in Hawai'ian plate lunch or fresh poke bowls at a local eatery in Honolulu. Options like Poke by the Pound or The Pig and The Lady offer delicious dishes that showcase the authentic flavors of Hawaii.

In the afternoon, embark on a hike up Diamond Head Crater Trail. This moderate trek offers panoramic views of Honolulu and the surrounding coastline, making it a must-see attraction for outdoor enthusiasts and photographers alike.

As evening approaches, enjoy a leisurely dinner at a restaurant such as Tiki's Grill and Bar, Monkeypod Kitchen or Hana Koa Brewing Co., where you can savor Hawai'ian-inspired cuisine and refreshing cocktails.

Cap off your day with a memorable sunset cruise departing from the marina. Alternatively, if it's a Friday, don't miss the vibrant fireworks display at 7:45 pm, illuminating Waikiki's skyline and providing a perfect conclusion to your unforgettable journey through Oahu's North Shore and Waikiki.

Need to know

These two days offer a perfect blend of relaxation, adventure and cultural exploration, allowing you to experience the best of what Oahu has to offer.

Have additional time? Explore Waimanalo Beach, visit Pu'u 'Ualaka'a State Wayside for a view of Honolulu or reserve a time at Hanauma Bay for snorkeling.

This guide is part of our ongoing series on travel to Oahu. For more travel tips, check out my trip report, A Love Letter to Lovers Beach: Los Cabos' Ultimate Escape.