Oahu North Shore itinerary: 5 days for a first trip
A 5-day Oahu itinerary built around the North Shore and its surf culture. Two days are on the North Shore itself: Sunset Beach and Giovanni's shrimp truck, then Haleiwa shave ice and a Waimea Bay sunset. The rest of the trip gets you there and shows the other side of the island: Waikiki and Diamond Head first, then Kualoa Ranch, the Kaneohe sandbar, the Lanikai Pillbox hike and Kailua town.
You'll want a car for the drives, and a boat or kayak for the sandbar. It's one of the sample trips inside the Wanderjoy app, so you can open this exact plan on your iPhone with code HAWA1 and change anything. Check the state park sites before you go.
The whole plan on one map
One color per day. Pick a day to see just its route.
Day by day
Day 1Waikiki Beach · Diamond Head State Monument · Kalakaua Avenue
Waikiki Beach Morning Surf7:30 AM
Catch small morning waves perfect for beginners.
Diamond Head Summit Trail11:00 AM
1.6-mile round trip with steep stairs near the summit. Bring water and sunscreen.
Kalakaua Avenue Shopping & Dinner4:00 PM
Day 2Kamehameha Highway · North Shore · Giovanni's Shrimp Truck
Scenic North Shore Drive8:00 AM
Take H-2 north then Kamehameha Hwy along the coast. Stop at the Dole Plantation for pineapple whip on the way.
Sunset Beach11:00 AM
One of the most famous surf breaks in the world. Watch pro surfers from the wide sandy beach in winter.
Giovanni's Shrimp Truck, Haleiwa2:00 PM
The original garlic shrimp truck since 1993. Get the scampi—messy but legendary.
Day 3Kualoa Ranch · Kualoa Regional Park · Kaneohe Bay Sandbar
Kualoa Ranch Tour8:30 AM
Filming location for Jurassic Park, Lost, and Hawaii Five-0. Stunning valley surrounded by cliffs.
Mokolii (Chinaman's Hat) Viewpoint12:00 PM
Mokolii Island looks like a pointed hat from the shore. Best photos from Kualoa Regional Park.
Kaneohe Sandbar (Ahu o Laka)3:00 PM
Best at low tide when you can stand waist-deep in turquoise water.
Day 4Kaiwa Ridge Trail · Kailua · Kailua Town
Lanikai Pillbox Hike7:00 AM
Go at sunrise for jaw-dropping views of the Mokulua Islands. Short but steep trail (1.8 miles round trip).
Lanikai Beach10:30 AM
Consistently rated one of the world's best beaches. Powder-soft sand, crystal-clear water, Mokulua Islands backdrop.
Kailua Town Afternoon2:00 PM
Charming windward town with local boutiques and great food. Grab acai at Lanikai Juice and relax.
Day 5Wahiawa · Haleiwa Town · Waimea Bay Beach Park
Dole Plantation9:00 AM
Try the Dole Whip—pineapple soft serve that's worth the hype.
Haleiwa Town & Shave Ice12:00 PM
Laid-back surf town with art galleries, surf shops, and food trucks. Get shave ice at Matsumoto's (since 1951)—add condensed milk and azuki beans on the bottom.
Waimea Bay Sunset5:00 PM
One of the best sunset spots on the island. Peaceful way to end the trip.
Plan your own Oahu North Shore 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 HAWA1: 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 North Shore plan in Wanderjoy?
- Install Wanderjoy, then import trip code HAWA1. 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 North Shore plan for me?
- Yes. Give Wanderjoy your dates and how you like to travel, and it drafts a day-by-day Oahu North Shore itinerary on a map for you.
