5-Day Journey Through Oahu

Advisor - Holly Huff
Curated By

Holly Huff

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  • Oahu

  • Hawai'i

  • Active Travel

  • Adventure Travel

  • Coastal

  • Local Food

  • Sightseeing

  • Outdoors

Sunset on beach.
Curator’s statement

Oahu is the third-biggest of the Hawaiian Islands and is where Honolulu, the state capital, is located. Oahu is also the most popular of the Hawaiian Islands to visit. A visit to Oahu will provide you with incredible beaches and other activities to do and see. Bonus is that the weather is incredible year-round. So, this is a great place to go if you're trying to escape the cold in the winter months. There is less than a 10-degree difference between the summer and winter, so any time of year is terrific.

The Fora Difference

Book with Holly to access exclusive perks and experiences on your trip.

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Killer perks

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Insider knowledge

Expert advice from people who’ve actually been there

Where to stay

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The Royal Hawaiian, a Luxury Collection Resort, Waikiki

Iconic pink-walled property on Waikiki Beach with 528 warmly decorated rooms and suites.

Fora Perks
  • $100 hotel / resort credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

The Moana Surfrider

In the heart of Waikiki Beach, a low-rise original with lush oceanfront gardens and outdoor restaurants.

Fora Perks
  • $100 hotel / resort credit.

  • Welcome amenity.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

Outrigger Reef Waikiki Beach Hotel

Immerse yourself in the spirit of aloha, where the gentle rhythm of the ocean harmonizes with warm Hawaiian hospitality.

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Advisor - Holly Huff

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Day 1: Arrival


After you arrive in Oahu and check in to one of the incredible hotels located in Waikiki, I'm sure you'll be hungry after the flight. It's time to try some incredible restaurants on the Island—a visit to Dukes, located in the Outrigger Waikiki Beach Resort, is a great start. Not only will you enjoy incredible food, but the view is also incredible. Afterward, you can take a walk on the beach and enjoy the sound of the waves or have a cocktail at one of the many beach-side bars.

Day 2: Waikiki Beach


Start your day on Waikiki Beach with a morning swim.

For lunch, take a trip to the famous Helena's Hawaiian Food restaurant, and you won't be disappointed. In 2000, Helena's received a James Beard award and no trip to Honolulu is complete without a visit. Make sure you go early since seating is limited and the restaurant is always busy.

Time to explore Waikiki! There are so many options of things to do! You can spend your afternoon relaxing on the beach, swimming in the ocean or exploring the many shops on Kalakaua Avenue. If you want to shop, visit the Ala Moana Center or the Royal Hawaiian Center for luxury items.

Day 3: Pearl Harbor Memorial


No visit to Honolulu is complete without a visit to the Pearl Harbor Memorial. You can spend a whole day exploring and learning the history of what happened on that tragic day.

After your long day at the Pearl Harbor Memorial, enjoy a Mai Tai at the Mai Tai bar in the Royal Hawaiian Hotel in the evening. This is where we stayed and the service and location are incredible. The pink hotel is an iconic landmark in Waikiki and even if you choose not to stay there, a visit to the Mai Tai bar will make an enjoyable evening as you sip a Mai Tai and listen to the waves.

Day 4: Diamond Head

Diamond Head

After enjoying the view of Diamond Head while visiting Waikiki Beach, it is time to climb it. The hike up Diamond Head is about 1.6 miles, so make sure you are prepared and wear comfortable shoes.

If hiking isn't your thing, take a trip to the Aquarium or Zoo located in Honolulu. Multiple animals are not native to Hawaii and when it's discovered that someone illegally smuggled one in, it ends up at the Honolulu Zoo. In the evening, take a drive to the North Shore to stay overnight so you have a full day to enjoy it.

Day 5: Polynesian Cultural Center

Big Island Hawaii

After a morning visit to the beach, head to the Polynesian Cultural Center to learn the history of the Hawaiian people. You'll spend a day exploring the different cultures and then enjoy a traditional Luau. After the Luau, you'll enjoy a show that tells the story of the Hawaiian people. Make sure you make reservations before you leave for Hawaii, since tickets sell out quickly. A visit to the Polynesian Cultural Center is an all-day event.

Need to Know

If relaxing on the beach is something you dream about, include a couple of extra days to enjoy the North Shore or Waikiki beaches. Also, no trip to Hawaii is complete without visiting one of the many shrimp trucks all over the Island or getting shaved ice. Both are incredible.

Looking for more inspiration on adventures in Hawai'i? Find more guides about traveling to Hawai'i written by your favorite travel experts (aka Fora Advisors).

Advisor - Holly Huff

Travel Advisor

Holly Huff

Get in touch with Holly

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This guide is part of our ongoing series on travel to Hawai'i.