Ever since my first trip to Oahu, I’ve been hooked on the island’s mix of tropical adventure and laid-back charm. Planning your own Oahu itinerary can feel a bit overwhelming—there’s just so much to see, from famous beaches and scenic hikes to historic sites and local eats. If you’re dreaming of turquoise water, lush mountains, and fresh poke bowls, you’re in the right place. In this guide, I’ll walk you through how I’d spend 5 days on Oahu: the must-dos, personal favorites, and a few low-key surprises. Whether you’re a first-timer or making a return visit, here’s how to make every day count on Hawaii’s most vibrant island.
Table of Contents
- Day 1: Waikiki Welcome & Diamond Head Hike
- Day 2: Pearl Harbor & Honolulu Culture
- Day 3: East Oahu Road Trip (Beaches + Views)
- Day 4: North Shore Surf & Food Trucks
- Day 5: Ko Olina Relaxation & Departure Tips
- Oahu Travel Tips
- FAQs
Day 1: Waikiki Arrival, Diamond Head, and Beach Time
There’s nothing quite like that first view of Waikiki Beach. I love starting my Oahu trip here: it’s lively, walkable, and a great home base for your first night or two.
- Morning:
Check into your hotel and wander down to Waikiki Beach. I always recommend grabbing a coffee from Island Vintage Coffee before dipping your toes in the sand. - Late Morning:
Head out early for the Diamond Head hike. It’s a classic for a reason—the views over Honolulu and the coastline are unforgettable. Go as early as you can to beat the heat and the crowds. The hike is about 1.6 miles round-trip, moderately steep, but the summit breeze is worth it. - Afternoon:
Cool off with a swim or rent a paddleboard at Waikiki. For lunch, I love heading to Marukame Udon for fresh, affordable noodles (yes, there’s a line, but it moves fast). - Evening:
Sunset is magical on Waikiki Beach. Grab a spot on the sand or head up to the rooftop at The Deck for cocktails and those classic sunset photos.
Where to Stay: Waikiki offers everything from boutique hotels to luxury resorts. I’ve enjoyed The Surfjack for its retro vibe and central location.
Day 2: Pearl Harbor History & Downtown Honolulu
Oahu’s past is as fascinating as its scenery. I always carve out a half day for Pearl Harbor and then balance it with something light and local in Honolulu.
- Morning:
Pearl Harbor National Memorial is essential for first-timers. Book your USS Arizona tickets in advance. The exhibits and memorial are moving and worth a few hours of your morning. - Lunch:
Head into downtown Honolulu. The Chinatown area is great for lunch—try The Pig and the Lady for modern Vietnamese, or hit up a poke bowl spot. - Afternoon:
Walk through the historic district to see Iolani Palace and King Kamehameha Statue. If you’re an art lover, don’t miss the Honolulu Museum of Art. - Evening:
Take it easy with a stroll through Ala Moana Beach Park, or shop at Ala Moana Center. If you’re craving Japanese food, Shirokiya Japan Village Walk is a unique food court experience.
Day 3: East Oahu Road Trip – Beaches, Views & Adventure
Today’s all about the coastline! I love renting a car and making my way up the island’s windward (east) side.
- Morning:
Start with a sunrise at Lanikai Beach (it’s worth the early wake-up). The sand is powder-soft and it’s rarely crowded in the morning. - Midday:
Take the scenic drive along Kalanianaole Highway, stopping at Halona Blowhole Lookout and Makapu’u Point. If you’re up for a short hike, the Makapu’u Lighthouse Trail is one of my favorites for sweeping ocean views. - Lunch:
Head to Kailua town for brunch or lunch at Cinnamon’s or Over Easy. Don’t skip the local farmers market if you’re there on a Sunday. - Afternoon:
Relax at Waimanalo Beach or, if you’re in the mood for more adventure, try kayaking to the Mokulua Islands from Kailua Beach. - Evening:
Circle back toward Waikiki or spend the night in Kailua for a quieter pace.
Day 4: North Shore Surf Towns & Food Truck Eats
No trip to Oahu feels complete without a day on the North Shore. Even outside of winter’s big wave season, this area has a totally different vibe from Honolulu.
- Morning:
Hit the road early and stop at the famous Dole Plantation for a pineapple whip treat and a quick tour of the gardens. - Midday:
Arrive in Haleiwa, a laid-back surf town. I always grab a coffee at Coffee Gallery and then stroll the shops. From here, follow the coast to Waimea Bay, Shark’s Cove (great for snorkeling), and the Banzai Pipeline (legendary surf spot, especially in winter). - Lunch:
North Shore is food truck heaven! Try Giovanni’s Shrimp Truck or look for a poke bowl at Aji Limo. - Afternoon:
Chill at Sunset Beach or head out for a hike at Waimea Valley (there’s a waterfall you can swim in, which is rare on Oahu!). - Evening:
Stay for sunset on the North Shore—it’s one of the best on the island.
Day 5: Ko Olina Relaxation & Departure Tips
Your final day is perfect for winding down, especially if you have a late flight. Ko Olina’s lagoons are ideal for a calm morning.
- Morning:
Head to Ko Olina Lagoons for swimming and a relaxed vibe. The walking paths here are beautiful, and it’s a great spot for families or anyone wanting a peaceful end to their trip. - Lunch:
Enjoy a leisurely brunch at Monkeypod Kitchen (their pies are worth saving room for). - Afternoon:
If time allows, stop by the Pearl Harbor Aviation Museum or do some last-minute shopping. - Departure Tips:
If you’re flying out late, keep in mind you can usually store your bags at your hotel. Give yourself extra time at Honolulu Airport—security lines can be long.
Oahu Travel Tips
- Getting Around: Renting a car makes exploring easy, but parking in Waikiki can be pricey. Plan ahead!
- Best Time to Visit: April–June and September–November for fewer crowds and pleasant weather.
- What to Pack: Reef-safe sunscreen, comfortable walking shoes, a rain jacket for sudden showers, and reusable water bottles.
Want more details on Oahu’s best beaches or where to stay? Check out my Ultimate Oahu Travel Guide for extra tips and personal picks!
Frequently Asked Questions (FAQs)
What’s the best area to stay on Oahu for first-time visitors?
I always suggest Waikiki for convenience, but the North Shore or Kailua are great if you prefer a quieter vibe.
Do I need a car to explore Oahu?
You can get by with shuttles and tours in Waikiki, but a rental car makes it much easier to visit the North Shore and East Oahu.
How many days do you need in Oahu?
Five days gives you enough time for beaches, hikes, history, and adventure—plus a bit of relaxation.
What are Oahu’s must-see spots for first-timers?
Diamond Head, Pearl Harbor, Waikiki Beach, North Shore surf spots, and at least one sunrise or sunset!
Are there good places to eat on a budget?
Definitely! Look for food trucks, local plate lunch spots, and casual poke shops all over the island.
Conclusion
Oahu is one of those places I find myself daydreaming about long after I leave—the island truly has a bit of everything. If you follow this 5 day Oahu itinerary, you’ll experience the perfect mix of adventure, culture, and pure relaxation. If you have questions or want more ideas for your trip, feel free to leave a comment or browse my other Hawaii guides on Travel with Zee. Safe travels, and enjoy every minute under those Hawaiian skies!
