Oahu Diamond Head & Manoa Falls: Hike with Guide + Pickup

Summary

Diamond Head Crater & Rainforest Waterfall Walk

You’ll hike Oahu’s famous Diamond Head crater with a local guide and take in sweeping views over Waikiki before refueling with breakfast at a local spot. Then wander through bamboo forests to reach Manoa Falls’ cool misty pool. With hotel pickup included and stories from your guide along the way, it’s an easygoing day that lingers long after you leave Hawaii.

What’s the experience like?

I still remember the first few minutes after our driver picked us up in Waikiki — the city was just waking up, but by the time we reached Diamond Head, the air already smelled faintly of plumeria and sunscreen. Our guide, Kaleo, handed out water bottles and grinned when he saw my old sneakers (“they’ll do,” he said). The hike up wasn’t as tough as I’d feared, but those last steps to the top made my legs wobble. Standing there, wind in my face and Waikiki spread out below — it’s hard to describe. I kept thinking about how many people have stood right here, squinting into that same bright blue.

Afterwards, we grabbed breakfast from this tiny spot Kaleo recommended (I can’t pronounce the name — Li laughed when I tried), then ate it at a lookout where some locals were setting up for a picnic. The spam musubi was salty and warm; I’m not sure if it was the food or just being outside that made everything taste sharper. We had time to just sit and watch the waves before heading to Manoa Falls. That part surprised me — how quickly you go from city to jungle on Oahu.

The trail at Manoa was muddy in places, bamboo creaking overhead whenever the wind picked up. It felt quieter there, except for birds and someone’s distant laughter echoing through the trees. When we reached the waterfall, everyone got quiet for a minute — maybe tired, maybe just taking it in. I touched the cold spray on my face and thought about how different this felt from any other day trip I’ve done. On the way back, Kaleo pointed out places we could visit if we wanted — parks, statues (he told a story about Duke Kahanamoku that stuck with me), even a shopping mall bigger than any I’ve seen at home.

Step-by-step itinerary

Day 1 — Waikiki and Diamond Head Hikes

• Hotel pickup in Waikiki
• Visit Waikiki Beach volleyball area
• Hike Diamond Head crater
• Hike to Manoa Falls
• Pass by Ala Moana Center
• See Duke Kahanamoku Statue
• Visit Kapiolani Park

Top questions

How long does the Diamond Head hike take?

The round trip hike up Diamond Head takes about 90 minutes.

Is hotel pickup included for this tour?

Yes, hotel pickup and drop-off are included for all Waikiki hotels.

Do I need special hiking shoes?

No special shoes are required; comfortable sneakers are fine for both hikes.

How difficult is the Manoa Falls hike?

The Manoa Falls trail is family-friendly and takes around 60 minutes round trip.

Is breakfast included on this tour?

You’ll stop at a local spot to grab breakfast to-go (cost not specified in reference).

Are guides local Hawaiians?

Your guide is local and shares stories about Oahu’s history and culture during the tour.

Can I customize stops on this private tour?

If time allows after both hikes, your guide can show you more spots based on your interests.

Is an audio guide provided at Diamond Head?

Yes, an audio guide is included for your self-guided hike up Diamond Head.

What’s included

Your day includes hotel pickup and drop-off in Waikiki, entry fees for both hikes, a professional local guide sharing live commentary along the way, plus an audio guide for Diamond Head so you can go at your own pace before rejoining your group for breakfast and more exploring.