Peddle your bike or zoom on an electric 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, established in 1877 by King Kalakaua and named after Queen Kapiolani, is Honolulu's oldest public park, to discover its history. Then we head down to the Waikiki Natatorium, a war memorial constructed in 1927, featuring a saltwater swimming pool and stadium, dedicated to the Hawaiian servicemen who served in World War I. Here, you will see where famed Duke Kahanamoku trained for the 1912, 1920, and 1924 Summer Olympics. Duke won gold medals in the 100-meter freestyle in both the 1912 Stockholm Olympics and the 1920 Antwerp Olympics.

As the tour progresses, you'll be treated to a visit to a secluded green sand beach, rich with the mineral olivine, which is eroded from volcanic rocks at the base of Diamond Head, offering a rare view of an extraordinary coastal landscape. Along the route, you'll catch glimpses of opulent residences showcasing the architectural marvels dotting this affluent area known as the "Beverly Hills of Hawaii".

The ride continues with a climb to the Diamond Head Lighthouse Lookout, situated 150 feet above sea level, where you can enjoy panoramic views of surfers riding the crowded waves of the surf breaks known as "Cliffs" and "Lighthouse". Further exploration leads to views of Doris Duke’s Shangri-La Mansion in the exclusive Black Point neighborhood, followed by a short climb to a vantage point near the former Hawaii Five-O studios.

The centerpiece of the tour is a guided hike into the heart of Diamond Head Crater. This 45-minute to 1-hour trek up 300 feet offers an in-depth look at Hawaii's natural history and its role in WWI. The summit provides awe-inspiring vistas of Oahu's southeastern coastline.

For this portion of the tour, guests are required to secure their own hiking permits for a 9:00am entry into Diamond Head, which can be booked 30 days advance. It's recommended to take a screenshot of the QR code from the permit and text it to the tour operator for seamless entry. If the 9:00am slot is full, any available time slot can be booked as part of the VIP experience.

Lunch is included! Following the hike, the tour winds down with a well-deserved, nutritious local lunch. Throughout the day, sunscreen, water, sports drinks, and snacks are provided to keep you energized and protected from the sun. This tour is not just a cycling adventure but a comprehensive cultural and historical immersion into the heart of Oahu.

**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.

Click here to reserve your Diamond Head Crater entry separately.

E-Bike Tour Option

For the Diamond Head Bike to Hike tour, electric bikes (e-bikes) are available, offering pedal assistance to help participants easily manage the ride's terrain and enjoy the scenic climb. These e-bikes are equipped with various power settings, ensuring a comfortable and accessible experience for riders of all fitness levels.

Included

• Friendly Knowledgable Bike Tour Guide
• High Quality Bicycle and Helmet
• E-Bike Tours available
• Guide talks to you throughout ride via Bluetooth speaker on your bike
• 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