Oahu itinerary: 5 days for a first trip
Five days on Oahu for a first trip: Waikiki and a sunset with live music; Diamond Head and a plate lunch; Pearl Harbor, ʻIolani Palace and a harbor-front dinner; a North Shore day in Haleʻiwa and Waimea Bay; then Hanauma Bay, the Makapuʻu Lighthouse Trail and the Nuʻuanu Pali Lookout.
It's one of the sample trips inside the Wanderjoy app, so you can open this exact plan on your iPhone with code MAHALO and change anything.
The whole plan on one map
One color per day. Pick a day to see just its route.
How a plan looks in the app
A Oahu trip being revealed in Wanderjoy, pin by pin.
Day by day
Day 1Waikiki Beach · Kalākaua Ave · Halekulani
Waikiki Beach Morning9:30 AM
Start with the classic — rent a board or just float with Diamond Head in view.
Duke Kahanamoku Statue12:00 PM
The lei-draped statue of the father of modern surfing, right on Waikiki Beach.
Sunset at House Without a Key5:30 PM
Live Hawaiian music and hula under the century-old kiawe tree while the sun drops behind the ocean.
Day 2Diamond Head State Monument · Kanaina Ave · Sans Souci Beach
Diamond Head Summit Hike7:00 AM
The 0.8-mile crater-rim trail ends at a WWII bunker with the best 360° view on the island.
Rainbow Drive-In Plate Lunch11:00 AM
A classic Honolulu plate-lunch counter five minutes from the crater.
Kaimana Beach Sunset5:00 PM
The locals' end of Waikiki — calm, uncrowded water by the Natatorium with a straight-on sunset view.
Day 3Pearl Harbor · Honolulu · N Nimitz Hwy
Pearl Harbor National Memorial8:00 AM
ʻIolani Palace1:00 PM
The only royal palace on U.S. soil, home of Hawaii's last monarchs.
Nico's Pier 38 Dinner5:30 PM
Harbor-front fish house right at the Honolulu fish auction pier — the furikake-crusted ahi comes off the boats you're looking at. Order at the counter and grab a dockside table.
Day 4Haleʻiwa · Sunset Beach · Waimea Bay
Haleʻiwa Town9:30 AM
Surf-town main street of boutiques and food trucks — the hour drive from Waikiki is worth it. Matsumoto Shave Ice with condensed milk is the mandatory stop.
Ted's Bakery Haupia Pie12:30 PM
The chocolate-haupia (coconut cream) pie that fuels the North Shore surf scene — grab a plate lunch and a slice, then eat across the road at Sunset Beach.
Waimea Bay Lookout3:00 PM
Glassy jump-rock swimming in summer, 30-foot big-wave arena in winter. If the surf is up, watch from the beach — and check Pipeline 10 minutes up the road too.
Day 5Hanauma Bay Nature Preserve · Makapuʻu Point · Pali Hwy
Hanauma Bay Snorkel7:30 AM
Oahu's best beginner reef — 400+ fish species in a sheltered volcanic bowl.
Makapuʻu Lighthouse Trail11:30 AM
No shade on the trail; bring water and a hat.
Nuʻuanu Pali Lookout4:00 PM
Sweeping windward-coast panorama from the cliff where Kamehameha won Oahu in 1795. It's seriously windy — hold your hat.
Plan your own Oahu trip
Different dates or a different pace? Wanderjoy drafts a plan around yours.
Get this trip on a map in the app
Install Wanderjoy and import trip code MAHALO: this exact plan opens in the app, ready to change.
On a computer? Open the trip page for a QR code to scan with your iPhone.
Questions
- How do I open this Oahu plan in Wanderjoy?
- Install Wanderjoy, then import trip code MAHALO. The same 5-day plan opens in the app with every stop on the map, and you can change it from there.
- Can I change the plan?
- Yes. Add, edit or reorder stops, switch days around, and keep trip notes next to the plan.
- Can Wanderjoy make a different Oahu plan for me?
- Yes. Give Wanderjoy your dates and how you like to travel, and it drafts a day-by-day Oahu itinerary on a map for you.
