I lived on Oahu, Hawaii for years, and I know that it is so much more than Waikiki in Honolulu! Spend 5 days on the island and explore the varied landscapes, eats, and activities. 

Hawaii, USA

Kailua, HI, USA

Haleiwa, HI, USA

Honolulu, HI, USA

5 Days on Oahu: Beyond Waikiki!

Headed to Honolulu/O'ahu for the first time? This is a great 4 day itinerary for you highlighting great things to see, beautiful beaches, amazing eats, and hits the stuff I feel like all first timers should see. It's jam packed, so if it's too much, save some for your next visit! You'll be back.

O'ahu for First Timers

Oahu. Home of white sand beaches, amazing hikes, epic surfing, the historic Pearl Harbor memorial, and a. lot. of. traffic. It’s the most visited island as well as the most populous which does lead to more crowds and traffic than you will see on the other Hawaiian islands.

BUT, don’t let this deter you from visiting. It’s busy for a reason. There are so many fun things to do and see that a vacation to Oahu will soon be one of your favorites. This guide will show you how to spend ONE weekend on Oahu. In my (slightly biased) opinion it’s the best 3-day Oahu itinerary for adventure lovers.

Kahuku

Kailua

Haleiwa

Waimānalo

Waikiki

Kaneohe

Diamond Head

Honolulu

One Weekend on Oahu: A Complete 3-day Itinerary 

If you're looking for the perfect island getaway that offers a mix of breathtaking natural beauty, rich history, and modern amenities, look no further than Oahu, Hawaii.

This stunning island boasts some of the most beautiful beaches in the world, like Waikiki Beach and Lanikai Beach, where you can soak up the sun, surf, or snorkel in crystal-clear waters.

But Oahu is much more than just beaches; it's also home to iconic hikes whether you're a beginner or an expert. And with its vibrant nightlife, incredible food scene, and world-class shopping, Oahu has something for everyone.

👉 Save yourself hours of research and planning by choosing from my list of recommendations.

Includes daily:
- Breakfast
- Activity
- Lunch
- Activity
- Dinner
- Activity

✨  This guide is perfect for families, small groups, and solo travelers.

Highlights:
☕️ 2 cafes
🍳 3 breakfast
🐟 3 poke spots
🥘 9 lunches/dinners - that are not poke
🍨 7 shave ice & sweets
🏖️ 12 beaches to relax at
🤿 2 beaches for snorkeling
🏛️ 4 landmarks/sites
🛍️ 3 shopping
🌃 5 hotel recommendations - including every budget
🚊 Transportation tips
📍 5 Customizable Google Maps 

Kaneohe, HI, USA

Insider's Guide to Oahu - Full Itinerary 5 days

Embark on an unforgettable Hawaiian adventure with this comprehensive guide. Delving into the unique charms of each major island. From the bustling city life of Oahu to the lush landscapes of Maui, the dramatic cliffs of Kauai, and the diverse wonders of the Big Island, we offer Where to Stay, What to Eat & Drink, and What to Do recommendations tailored to each island's distinctive character. Immerse yourself in the aloha spirit, from romantic beachfront resorts to local culinary delights and breathtaking adventures. Make your trip an unforgettable journey through the enchanting Hawaiian archipelago with this expertly curated guide.

Hawaiian Island Guide

O'ahu, Hawaii

Aloha! Welcome to my comprehensive guide of what to do, see & eat on the island of Oahu! 🌺

Includes a mini guide to the North Shore! 
The best beaches, food trucks & more! 


Waikiki, Honolulu, HI, USA

Oahu, Hawaii, USA

Ultimate Guide to O'ahu, Hawaii (includes North Shore!) 

Laie

Kapolei

Koolauloa

Waipahu

North Shore

O’ahu, Hawaii

O‘ahu, Hawaiʻi | On a budget | Backpacking | November

North Shore, Waialua, Hawaii, USA

Hawaiʻi on a budget

A detailed itinerary for 5 days in Oahu, made with personal experience and hours of research. It includes the following:

✨where to stay - hotel and airbnb recommendations for all budgets

✨where to eat and drink - a wide array of eateries for all three meals, plus coffee shops and dessert spots 

✨what to do - plenty of activites for each day, including beaches, hikes and botanical gardens 

This itinerary is perfect for all travelers - including couples, solo travelers and families!

North Shore, Waialua, HI, USA

5 days in Oahu, Hawaii - Itinerary 

O'ahu, Hawaii is a paradise for nature lovers seeking the perfect island getaway. This 5-day itinerary is crafted for travelers who want to immerse themselves in O'ahu’s stunning natural landscapes. From its world-famous beaches to lush mountain hikes, this guide takes you through the best of the island's outdoor adventures and serene natural attractions. Whether you're exploring the scenic trails of Diamond Head, basking in the beauty of Lanikai Beach, or diving into the crystal-clear waters of Hanauma Bay, you’ll find endless opportunities to connect with nature.

Each day of this itinerary is packed with nature-based experiences, including hikes to panoramic coastal views, thrilling water activities, and gorgeous beaches for sunrise and sunset. In 5 days you'll be able to truly take in the island’s breathtaking diversity—from rainforests to volcanic craters—while also finding time to relax and enjoy the tranquil beauty of Hawaii’s unique ecosystems. Perfect for those who seek both adventure and serenity, this itinerary is your guide to experiencing O'ahu’s rich natural wonders at your own pace.

This itinerary is fully built out so you don't have to plan a thing once you touch down. It includes hotel recommendations, places to eat, drive times and directions, and tours. This itinerary is perfect for the solo traveler, couples, or families with children as there are multiple options provided for the hotels and tours.

Be sure to read through all of the notes for the places you plan to visit, as some tourist spots require booking a certain timeframe in advance (such as the USS Arizona Memorial, Diamond Head, and Hanauma Bay Nature Reserve). 

Looking to stay less than 5 days on the island? This itinerary will still work for you! You can absolutely pick and choose which recommendations to visit whether you want more relaxation or adventure. 

Looking to stay more than 5 days? Contact me on my Thatch profile or send me an email (michelle@sandmanntravels.com) and I can work with you to build out a longer itinerary based on your unique travel style.

O'ahu, Hawaii: 5 Epic Days for Nature Lovers

5 Days in Hawaii

After you have spent time with all the sealife, start packing up around 1 or 2 pm and head to your next stop: the famous Diamond Head hike!

Side note: You also need a reservation for this hike and it can be done here up to 30 days in advance.

Diamond Head is an easy (and busy) 1.8-mile round-trip hike to some of the best views of Waikiki Beach and the city. There’s even an old bunker you can go inside!

Bring proper sneakers--it's a rugged trail. It tends to get VERY crowded, so bring your patience, some water, and some sunblock and be prepared for amazing views of Waikiki at the top! PRO TIP: If small places aren't your jam, take a left at the 99 step staircase and stay outside.

Open from 7 am to 3:30 pm. $5 per person and $10 per vehicle. 

Non-Hawaii residents must book in advance and reservations may be made up to 30 days in advance.

Hike up to this stunning viewpoint of Waikiki and Honolulu 

A classic! One of the most recognized landmarks in Hawaii 

Diamond Head

What people say

Mentioned in these guides

About Diamond Head