Hike Diamond Head and Makapu'u with round-trip Waikiki transportation
Approx. 6 hours
Transport, water, park fees
Explore two of Oahu’s signature trails in one trip, with transportation between hikes and time for photos along the way. You’ll hike Diamond Head and the Makapu'u Lighthouse Trail over about 6 hours.
Not recommended if you are pregnant or have heart, neck, back, or joint problems, or a serious fear of heights. The hikes include stairs, uneven surfaces, inclines, and sections that may be slippery. Changing departure times may incur additional charges—confirm the amount with Greetwell before booking.
Cancellations or changes must be made at least 48 hours before the tour date. Cancellations within 48 hours are non-refundable. Tours booked within 48 hours of departure are final sale and cannot be modified or refunded.
Arrive a few minutes before your scheduled pickup time. Pickups can begin up to 10 minutes before the tour time, and your exact pickup time may be adjusted based on your location.
Be ready at the scheduled pickup time. The driver follows a strict schedule and can’t wait for late arrivals.
Wear comfortable clothing suitable for walking and sun exposure. Bring comfortable walking shoes, a camera or smartphone, and sun protection (hat, sunglasses, and sunscreen).
Queen Kapiolani Hotel (if you are not staying in Waikiki)
Rising above the eastern edge of Waikiki, Diamond Head draws you in with its unmistakable silhouette against the Pacific sky. The crater's sun-bleached slopes and the steady ocean breeze greet you well before you reach the trailhead. Once inside Diamond Head State Monument, the path winds through tunnels and up concrete switchbacks toward a summit that rewards every step with sweeping views of Oahu's southern coastline stretching in both directions.
Kaimana stands out for making popular Oahu activities genuinely hassle-free. Travelers consistently praise how the company removes the stress of parking, gear rental, and logistics at places like Diamond Head and snorkeling spots. The convenience factor is huge here: quality snorkel equipment, optional beach extras like chairs and umbrellas, and perfectly timed shuttle schedules that get you places early to beat the crowds. The guides really shine through in these reviews. Orlando, Tommy, Matthew, and Adam all get called out by name for being knowledgeable, friendly, and genuinely fun to travel with. They share local history and practical tips throughout trips, creating an experience that feels more personal than your typical shuttle service. One reviewer mentioned feeling a bit rushed with 2 hours at Diamond Head instead of the expected 3, but otherwise the timing seems to work well. The snorkeling crew, including Mary and Katie, earn special praise for making beginners feel comfortable and safe in the water. If you want Hawaiian adventures without the planning headaches, this is a solid choice.
I did the Diamond Head & Manoa Falls combo through Kaimana, and I highly recommend going with them. I was a solo traveler, so being able to get to, inside, and out of the parks without having to rent my own car or worry about spotty service for a ride-share was an amazing experience. The highlights of booking with them are effective communication (I knew exactly what was going on and where to be), punctual (driver picked me up exactly when my assigned time was), and above & beyond (free walking sticks to borrow for Manoa Falls, free water, and bug spray). My driver, Matthew, made the trip especially more entertaining during the drives and was super helpful with the fun facts he provided along the way. I would definitely book with them again! I just hope they add more excursions and more availability days/times to their selection.
Eric Zhao
June 14, 2026
I did the Diamond Head & Manoa Falls combo through Kaimana, and I highly recommend going with them. I was a solo traveler, so being able to get to, inside, and out of the parks without having to rent my own car or worry about spotty service for a ride-share was an amazing experience. The highlights of booking with them are effective communication (I knew exactly what was going on and where to be), punctual (driver picked me up exactly when my assigned time was), and above & beyond (free walking sticks to borrow for Manoa Falls, free water, and bug spray). My driver, Matthew, made the trip especially more entertaining during the drives and was super helpful with the fun facts he provided along the way. I would definitely book with them again! I just hope they add more excursions and more availability days/times to their selection.
Eric Zhao
June 14, 2026
Ride a Waikiki shuttle and hike Diamond Head at your own pace
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