Recommended 30-Day Itinerary for Exploring the North Shore of Oʻahu

Below is a 30-day detailed itinerary for exploring Haleʻiwa and the North Shore of Oʻahu, focusing on the dining, shopping, and activity locations you’ve provided. This plan is designed so you can explore leisurely, see a variety of local attractions, taste some of the North Shore’s best food, and shop at unique local boutiques and galleries. Feel free to shuffle or swap days as you see fit!

Day 1 – Arrival & Haleʻiwa Introduction

Morning

Afternoon

Evening

Day 2 – Surf Culture & Beach Time

Morning

Afternoon

Evening

Day 3 – Haleʻiwa Store Lots & Galleries

Morning

Late Morning & Afternoon

Evening

Day 4 – Haleʻiwa Art & Boutiques

Morning

Afternoon Art Tour

Lunch

Evening

Day 5 – Shrimp Trucks & Historic Haleʻiwa

Morning

Lunch

Afternoon

Evening

Day 6 – Stand-Up Paddle & Watersports

Morning

Lunch

Afternoon

Evening

Day 7 – Gallery & Shop Hopping in North Shore Marketplace

Morning

North Shore Marketplace (66-250 Kamehameha Hwy)

Lunch

Evening


Day 8 – Boutique Day & Local Crafts

Morning

Shopping

Lunch

Afternoon

Evening


Day 9 – Historical & Cultural Exploration

Morning

Midday

Lunch

Afternoon

Evening


Day 10 – Beach & Food Truck Fun

Morning

Lunch

Afternoon

Evening


Day 11 – Outdoor Adventures & Snorkeling

Morning

Lunch

Afternoon

Evening


Day 12 – Relaxed Shopping & Sunset Dinner

Morning

Afternoon

Lunch

Evening


Day 13 – Explore Waimea Valley & Surrounds

Morning

Lunch

Afternoon

Evening


Day 14 – Art & Custom Jewelry Day

Morning

Afternoon

Lunch

Evening


Day 15 – Local Weddings & Events

Morning

Midday

Afternoon

Evening


Day 16 – Explore Haleʻiwa Shopping Plazas

Morning

All-Day Shopping (66-145 Kamehameha Hwy area):

Dinner


Day 17 – Local Style & Accessories

Morning

Afternoon

Lunch

Evening


Day 18 – Photos & Local Keepsakes

Morning

Afternoon

Evening


Day 19 – Health & Wellness

Morning

Afternoon

Lunch

Evening


Day 20 – Arts & Crafts (Second Round)

Morning

Afternoon

Lunch

Evening


Day 21 – Beach Gear & Swimwear Finds

Morning

Afternoon

Lunch

Evening


Day 22 – Leisurely Beach & Food Day

Morning

Afternoon

Evening


Day 23 – Pearl & Jewelry Day (Second Round)

Morning

Afternoon

Evening


Day 24 – Water Adventures (Second Round)

Morning

Afternoon

Lunch

Evening


Day 25 – Spend Time in Pupukea

Morning

Afternoon

Lunch

Evening


Day 26 – Relaxation & Personal Favorites

Morning

Afternoon

Lunch

Evening


Day 27 – Last-Minute Shopping & Gifts

Morning

Afternoon

Lunch

Evening


Day 28 – Scenic Drive & Photo Day

Morning

Afternoon

Lunch

Evening


Day 29 – Final Rounds of Food & Souvenirs

Morning

Afternoon

Lunch

Evening


Day 30 – Farewell North Shore

Morning

Before Leaving

Depart


Additional Tips & Reminders

Enjoy your extended stay exploring the best shopping, dining, and ocean activities that Haleʻiwa and the North Shore have to offer! Aloha!