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Bike Tour of Diamond Head

Location: Waikiki, Oahu

Peddle your bike through the streets of Waikiki on your way to the beautiful Diamond Head crater hike. Along the way roll through the wealthy mansion district of Kahala and past historic WWII sites. Your bike tour guide will keep you interested and having fun while explaining fun facts and historical information along the way to give you a better appreciation of the beautiful Waikiki.

What to Expect

We meet early at the Kuhio Beach Banyan Tree, Waikiki Beach 7:30 am to avoid crowds and the heat on the crater trail.

After your bike fitting and safety instruction, we roll onto Kapiolani Park to discover its history then we head down to the WW1 Natatorium Memorial to see where famed Duke Kahanamoku and others trained for the Olympics.

You’ll get to visit a secluded green sand beach at the base of Diamond Head; see the Disney house and roll past other homes from the marvels of wealth.

We then pedal up 150 feet to the Diamond Head Light House Lookout. From this advantageous view, you can see the surfers enjoying the placid waters of Paradise.

From here, we observe Doris Duke’s Shangri-La located in the wealthy Black Point neighborhood. After a short 100' elevation gain, we arrive near the Hawaii FIVE-O studios where they film this ongoing series. Next, we head into Diamond Head Crater 150' climb and park our bikes for a 45 minute to 1-hour hike, 300' climb filled with lots of Hawaiian and WWI history. Along the way, you’ll experience incredible views of Oahu’s south and east facing shores.

After the hike and photos, we descend to a healthy local lunch on us. Sunscreen, water, sports-drink, and snacks provided.

**NOTE: This tour has a hilly terrain and includes a walking hike to the top of Diamond Head. Bike Tour Ride and Hike total, 10 Miles.


  • Friendly Knowledgable Bike Tour Guide
  • Quality Bicycle and Helmet
  • Photo-Shoots at Every Location
  • Healthy Local Lunch
  • Sunscreen
  • Water, sports drinks, and snacks
  • We don't accept any children under 12 years old or shorter than 4.3ft


4 hours


Meet at the Kuhio Beach Banyan Tree, Waikiki Beach

Cancellation Policy

Full refund if canceled within 24 hours of your tour departure.