We recently returned from an unforgettable Hawaii adventure, and our two nights in Waikiki set the tone perfectly. If you’re heading to Hawaii for the first time and thinking about how to kick it off with style, here’s how we did Oʻahu—and what I’d recommend to make the most of your stay.
✈️ Arrival Day: Limo Surprise & Waikiki Vibes
We landed in Honolulu at 3:45 PM HST, and I had a surprise waiting: a pre-booked limo service to whisk us to our hotel. It was a small splurge that made a big impact—especially with the fresh leis I pre-arranged for everyone. The kids were totally surprised and loved it!
Arrival Tip: A pre-booked transfer (especially after a long flight) is worth it. It’s not that much more than an Uber, and the leis made it feel extra special.
🏨 Where We Stayed: Hyatt Regency Waikiki
The Hyatt Regency Waikiki gave us the perfect home base—just steps from the beach and the iconic King Kamehameha statue. Our city-view room on the 30th floor gave us beautiful views of the mountains and Diamond Head in the distance.
🍹 First Night: Monkeypod + Sunset Magic
After checking in, we strolled through a few shops (can’t resist those ABC stores!) and walked to Monkeypod for dinner. This is a fun, casual spot—and my husband crowned their Mai Tai the best on the island (he taste-tested many).
We ended the evening with a gorgeous Waikiki sunset before crashing—hello jet lag!
Day 2: Pearl Harbor, Surfing, and Sunset Views
We started early with a visit to Pearl Harbor, pre-booked for the morning. We took an Uber, but I recommend giving yourself extra time—Honolulu traffic is no joke.
We explored the Arizona Memorial and exhibits at the visitor center—powerful and educational.
Back in Waikiki, we grabbed a quick bite at the International Marketplace food court (perfect for families with picky eaters), then… surf’s up!
The kids had a surf lesson, and it was a major highlight. Waikiki is perfect for beginners thanks to its long, rolling waves—both kids caught multiple waves and were grinning from ear to ear.
Dinner that night was at Deck., known for its happy hour and incredible views of Diamond Head.
Travel Tip: Book your Pearl Harbor tickets in advance (56 days before the date you want to visit) and plan for early morning while still on East Coast time. Surf lessons in Waikiki are super family-friendly and unforgettable.
🌄 Day 3: Sunrise Hike + Malasadas
Another early start! We had a 6 AM reservation to hike Diamond Head. Ubered there, and while the crowds picked up near the summit, we were treated to an incredible sunrise view. Most people were looking at the sunrise, so we had the Waikiki views nearly to ourselves.
Post-hike reward: a stop at Leonard’s Bakery for their famous malasadas (hot, sugar-dusted heaven).
Back at the resort, we took a hula class, chilled by the pool, and then caught an inter-island flight to Kauaʻi.
🌟 Oʻahu Tips & Takeaways
2-3 days is perfect for Waikiki and key experiences.
Don’t skip: Pearl Harbor, Diamond Head, and surfing lessons.
If you have more time:
Rent a car and head to the North Shore for a more authentic vibe and food trucks.
Visit Bishop Museum—the planetarium show is a hidden gem!
Consider a visit to Kualoa Ranch (Jurassic Park, anyone?) or Gunstock Ranch for horseback rides and adventure.
For water lovers: look into a catamaran ride, snorkeling at Hanauma Bay, or paddleboarding on the North Shore.
Travel Tip: Waikiki is walkable and bustling—great for first-timers. But don’t be afraid to venture out for more culture and nature!
✨ Planning a Hawaii trip and not sure where to start? I’d love to help you design the perfect itinerary—relaxing, adventurous, or a little of both. Let’s make your Hawaii dreams a reality.
Priceless Gem Travel 