If you’ve never been to Oʻahu, Hawaii—it can be overwhelming to know where to start. Honolulu, the North Shore, Pearl Harbor, Diamond Head… how do you fit it all in?
This 4-day itinerary is based on the exact one I built for a real client and polished with personal recommendations.
🏝️ Day 1: Arrival + Waikiki
- Check into your hotel (ask me about ones that work best for families!)
- Walk the beach, grab shave ice, watch the sunset
- Dinner at Duke’s or Monkeypod
🏛️ Day 2: Pearl Harbor + Downtown
- Morning visit to Pearl Harbor (reserve tickets in advance!)
- Explore Iolani Palace or the Bishop Museum
- Optional: Trolley tour through historic downtown
🌋 Day 3: Diamond Head + East Shore
- Early hike up Diamond Head
- Scenic drive to Hanauma Bay or Makapu’u
- Afternoon swim or relax back in Waikiki
🌊 Day 4: North Shore Adventure
- Visit the Dole Plantation (briefly)
- Explore Haleʻiwa town, grab garlic shrimp
- Sunset at Waimea Bay or Laniakea Beach to spot turtles
🎁 Bonus tip: Want this in a printable? DM me HAWAII
Ready to plan your Hawaii trip without overwhelm? Schedule your free vacation planning call today or email me at melissa@thesingingsuitcase.com:
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