Kaimana Tours · Waikiki
A van collects you from your Waikiki hotel early in the morning, Kaimana Tours covers the park fees, and you climb with a bottle of water and a trail map. It's the cheapest way to get the reservation and transport sorted, and the early start keeps you ahead of the heat.
Kaimana Tours has run this shuttle long enough to collect more reviews than any other Diamond Head trip. The format is simple. A white Ford Transit van picks you up at one of 12 points in Waikiki, the park fees and reservation are already paid, and at the crater the driver hands out bottled water and a map. Then you're on your own for the hike up the 760-foot summit.
The thing to know is time. The trip lasts about three hours door to door, and guests report roughly an hour and a half to hike: one wrote that the driver told them to be back by 9:45. That's enough for most fit walkers, who reach the top in 30 to 45 minutes. One guest who walks fast still found it tight, with no time left to read the signs. If you're slow on stairs, the Go Tours shuttle gives about two hours.
Kaimana is upfront about who it suits: the listing doesn't recommend the hike for children under 3, for anyone over 65, or for travelers with back or heart problems. Pickup times differ by hotel, so contact Kaimana after booking to confirm yours. Staying outside Waikiki? The operator lets you park free at 2805 Monsarrat Ave and walk to the Queen Kapiolani Hotel to board.
Pickup times vary by hotel. Contact Kaimana to confirm yours; one guest wrote that the company rang the day before to check the details.
A white van collects guests at up to 12 points and drives about 15 minutes to the crater.
The driver hands out water and a map and tells you when to be back. Guests report about 90 minutes.
Paved path, then uneven rock, switchbacks, stairs and the lit tunnel to the Fire Control Station.
The van drops guests back at their Waikiki pickup points. Some drivers have water waiting after the hike.
★★★★★This was a 10/10 experience. Mark was our shuttle driver, very kind and knowledgeable of the island. When you get there they provided us with waters and a map and told us to be back my 945! The hike isn’t too hard, there’s many points you can stop and take a break.
★★★★★My husband and I are in the 60 age group and never hiked before but we did it!! You have to be mentally prepared and have plenty of water and the correct shoes and clothing to complete this hike. Matthew our bus driver was great he gave us all a pep talk before we got off the bus and water at the end for a reward!!
★★★★★It is challenging...take water. But I'm an almost 50 year old who rarely exercises and I was fine by taking a few breaks up.
★★★★★This is a convenient way to get to Diamond Head and back if you don’t have a rental car. Includes entry and plenty of time to hike without rushing.
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Guests report about an hour and a half between drop-off and pickup at the trailhead. Most fit hikers reach the summit in 30 to 45 minutes, so it works, but slow walkers have found it tight.
Park fees and the entry reservation, round-trip transport from Waikiki, bottled water and a trail map. Gratuities aren't included, and nobody guides you on the trail.
The listing says Kaimana does not recommend the hike for people over 65. Plenty of guests in their 60s have done it, taking breaks, but the trail has steep stairs and uneven rock. If you're unsure, a tour with more time, like the Go Tours shuttle, is kinder.
At 12 points in Waikiki, with the time set by your hotel. Contact Kaimana to confirm it. Guests outside Waikiki can park free at 2805 Monsarrat Ave and walk to the Queen Kapiolani Hotel.
Ready to book
The lowest price with the reservation handled: hotel pickup, water, a map and about 90 minutes to hike.
Diamond Head Hike Shuttle with Entry TicketsYour park reservation booked, a trolley ride from five Waikiki stops and about two hours to climb at your own pace.★ 4.8 · 2.5 hours · from $40
Diamond Head Early Hike with Entry ReservationA 5:30 a.m. pickup and entry at the 6 a.m. opening. A summit sunrise is realistic from November to March.★ 4.7 · 3 hours · from $50
Diamond Head Summit Shuttle with ReservationEntry, an air-conditioned minibus from Waikiki hotels and snacks, with about two hours at the crater.★ 4.8 · 3 hours · from $49