After your bike fitting and safety briefing, roll out through Kapiolani Park to uncover its fascinating history. From there, cruise down to the World War I Natatorium Memorial, where Olympic legends once trained. You’ll also stop at a secluded green sand beach nestled at the base of Diamond Head and pass the iconic Disney house along with other impressive homes showcasing Honolulu’s luxurious side.

Next, climb 150 feet up to the Diamond Head Lighthouse lookout for stunning views of surfers and the shimmering ocean. After the climb, stop near the Hawaii Five-0 studios before heading into Diamond Head Crater. There, you will park the bikes and set off on a 45-minute to one-hour hike through a path rich in Hawaiian and military history. Soak in panoramic views of Oahu’s southern and eastern shores before descending for a healthy, locally sourced lunch. 

Duration: Approximately 3 hours and 30 minutes