5 Days in Oahu for First-Timers

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Advisor - Dalila Calabrese
Curated By

Dalila Calabrese

  • Oahu

  • Beaches

  • Luxury Travel

  • Hawai'i

  • Adventure Travel

  • Relaxation

  • Islands

Diamond Head with the city of Oahu in the background and the ocean to the west.
Curator’s statement

Personally, when I think of paradise, Hawai'i comes alive in my head. I’ve been five times to this wonderful archipelago, but I just can’t get enough: the nature is wild, the sea is powerful yet calm and the people... the Hawai'ians are just the most welcoming, caring and wonderful people you will ever meet. If it’s your first time in Hawai'i and you only have a few days to spare, I would go and explore Oahu to make sure you’ll want to return and explore more and more and more of these amazing islands. If you’re looking for the comfort of having everything at your fingertips, from department stores to world-class restaurants, look no further than Waikiki and stay at the Westin Moana Surfrider: it’s an icon in Waikiki, just steps away from Duke’s Statue, and has possibly the best restaurant in the area. For a more relaxed and cool vibe in Waikiki, Kaimana is a great choice. My pick is, and will always be, the Four Seasons Ko’Olina: the impeccable service, the calm waters of the lagoon and the amazing spa make it the perfect stay in Oahu. If you’re on a romantic mission and want to splurge, however, head to the North Shore and stay at Turtle Bay!

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Day 1: Relax

A table set up with sandwiches and drinks on a patio overlooking the beach and blue umbrellas.

Settle into your hotel and relax at the beach. Head out to Waikiki for a stroll and dine at the Beach House at the Moana Surfrider. When in Waikiki, stop at the Christmas Store to buy unique ornaments and don’t miss the Honolulu Cookie Company: to die for!

Day 2: Lanikai & botanical gardens

A golden beach with blue waves and a mountain in the distance.

Start early your day and reach the beach of Lanikai before the wind rises, spend a few hours enjoying the sun and the beautiful settings, then head to the botanical gardens to admire the lush nature of Hawai'i. Stop for a late lunch at Duke’s Waikiki and enjoy the sunset at Diamond Head.

Day 3: Kaneohe & Kualoa Ranch

The Pali highway, a scenic road surrounded by palm trees and mountains.

Drive through one of the most scenic highways in the world, the Pali, and reach the harbor of Kaneohe from where you will sail to the sandbar: swim with turtles, sip your drink and lunch on board for a wonderful morning of sea and discovery.
Back on the land, head back to the jurassic era at Kualoa Ranch. Choose between one of the many tours available — don’t miss the Jurassic Park tour to get on the set of the blockbuster movie.

Day 4: Hanauma Bay & a luau

An aerial view of Hanauma Bay, with blue water encircled by green cliffs.

Spend the morning at the Hanauma Bay, a natural reserve where you will be able to swim with incredible marine life and enjoy a secluded beach in what it used to be a crater of a volcano. Spend your evening attending a traditional luau to discover more about the Hawai'ian culture.

Day 5: Waimea Valley

Shallow rock outcroppings next to the ocean.

Your adventure is almost over, so head to the North Shore and explore the Waimea Valley, swim under a waterfall and then head to Giovanni’s Shrimp Trunk for lunch. The garlic shrimps are to die for. Spend the afternoon hopping in between beaches and don’t miss the sunset at Waimea Beach Park. End your holiday with a dinner at Turtle Bay Resort, at the Beach House by Roy Yamaguchi, one of the greatest Hawaiian chefs.

Advisor - Dalila Calabrese

Travel Advisor

Dalila Calabrese

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This guide is part of our ongoing series on travel to Oahu. Looking for more travel inspiration? Check out my guide, 24 Hours in Napoli... With Kids!