Explore Oahu: A Complete Seven-Day Itinerary

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Advisor - Olivia Wilbur
Curated By

Olivia Wilbur

  • Beaches

  • Adventure Travel

  • Oahu

  • Tropical Vacations

  • Local Food

Advisor - Explore Oahu: A Complete Seven-Day Itinerary
Curator’s statement

Hawai'i has a special charm and culture that cannot be found anywhere else in the United States. The island of Oahu is filled with world-class beaches, activities, stunning landscapes and so much to do.

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Day 1: Waikiki

While I highly recommend you get out of Waikiki and explore the rest of the island, it's easy to spend time in Waikiki as there is so much to do and see! Walk around the city or walk along the beach, visit a market (I recommend Duke's Market), shop for souvenirs and explore the local cuisine. I highly recommend Island Vintage Coffee for good vibes and picture-perfect locally grown matcha and açaí bowls. Make your way to Ala Moana Beach Park for a stunning sunset, grab food from Paia Fish market for dinner and get a good night's rest to get your body back on track — no matter where you're coming from, you're probably jet-lagged!

Day 2: Southeast Oahu

Lanikai Beach

Start your day with a low-intensity, high-reward sunrise hike at the Makapu'u lighthouse trail. The hike is very short and the roads are paved, and the view is well worth getting up early! Depending on the time of year you visit, you may get lucky and spot some whales breaching the surface of the water as the sun comes up, so make sure to bring your binoculars.

If the tide is low enough and deemed safe, climb down and take a dip in the Makapu'u tide pools. Alternatively, if you are looking for a more challenging hike, Lanikai Pillbox, located just a bit north of the lighthouse is well-known for its incredible sunsets.

Either way, make your way north towards Kailua and stop in town for brunch at Sunrise Shack or Kono's. Afterwards, make your way to Lanikai Beach (my favorite beach on the island!) and take some time to just relax on the stunning beach and enjoy the sunshine and crystal clear water — you earned it!

After you've soaked up some sun, make your way along the coast back towards Waikiki, stopping at the Halona Blowhole to view a natural geyser and at Leonard's malasada truck for an authentic and delicious sweet treat.

Day 3: Honolulu

We went to Toa Luau in the North Shore!

Make your way into Honolulu. Explore Pearl Harbor, and grab some lunch in Chinatown. Head back towards Waikiki and entertain yourself at the Honolulu Zoo or Waikiki Aquarium, or take the rest of the day to lounge on the beach. After making your way back to your hotel and freshening up, head out to watch an authentic luau. Luaus take place every night all over the island, and include a dinner buffet, floral leis, an entertaining hula show often involving fire and cultural immersion.

Day 4: North Shore

Sunset Beach

Known for its world-class waves, the North Shore attracts surfers from all over the world. Even if you don't surf, there is no shortage of activities for everyone on the northern part of the island. On your drive up from Waikiki, stop at the Dole Plantation to try authentic Dole whip and to explore their insane gift shop with anything and everything pineapple-themed (and I mean everything). Right up the road, make sure to stop at GreenWorld Coffee Farm. See the beans growing on the trees in the only US state that grows its own coffee. Taste free samples, buy freshly made coffee and make sure to get some of your favorite coffee grounds to take hime with you.

On the North Shore, visit Kualoa Ranch to see where "Jurassic Park" was filmed and join a tour to experience the ranch from a different perspective. While on the North Shore, be sure to bring your snorkel to Shark Bay and Lanikea Beach to see wild see turtles and hordes of colorful fish! If you come in the winter, be sure to check out a surf competition at Banzai Pipeline. Watch the sunset at Sunset Beach, and visit the famous Giovanni's Shrimp Truck for dinner.

Day 5: North Shore

Acai bowls

Join a snorkeling or scuba diving tour — you won't regret it! Hawai'i is home to some truly incredible marine life, so take a day to spend on the water! If time permits, make your way into the historic Haleiwa town and just walk around and explore. Stop at Matsumoto for the best shaved ice, or Haleiwa Bowls for the best açaí. If you haven't already, try some Spam musubi!

Day 6: Head south

Ho’omaluhia Botanical Gardens

As you leave the North Shore and head back down south, make time to stop at the Ho’omaluhia Botanical Gardens — entry is free, and the views are simply breathtaking! Other things to do if you have the time include visiting the Kaneohe Sandbar, doing a waterfall hike (several options on different parts of the island), exploring the Diamond Head crater, visiting the Ko Olina lagoons on the west shore, going zip-lining through the palm trees, skydiving on the beach or whale-watching off the coast. If you stay for a Friday night, do NOT miss the beach fireworks show hosted by Hilton Hawaiian Village!

Need to know

Parking in Waikiki is very difficult.

Make sure to plan routes by plugging them into a GPS. Just because two points of interest look close on a map doesn't mean there isn't a huge mountain to navigate between the two.

Advisor - Olivia Wilbur

Travel Advisor

Olivia Wilbur

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