15 Diamond Head Tours on Oʻahu We Would Put on an Itinerary

1.Diamond Head Crater

★★★★★★★★★★5.0 · 943 reviews · 3 hours (approx.) · from $39Our pick

You’ll ride from Waikiki to Diamond Head, then hike the 1.6-mile loop at your own pace with a map, water, and entry fees covered. Drivers such as Matthew, Tommy, and Orlando provide helpful commentary before leaving you to tackle tunnels, stairs, and the 760-foot summit. Early pickup helps beat the heat, though the trail can still be busy.

“Great guide. Hike isn't as hard as you think but really busy so bring your patience. Views are insane but opt for the early tour as can get quite warm”

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2.Waikiki Trolley Green Line Diamond Head Shuttle

★★★★★★★★★★5.0 · 606 reviews · 1 hour (approx.) · from $22Best value

Take E Noa Tours’ Green Line trolley from Waikiki toward Diamond Head, passing the zoo, Kapiolani Park, local eateries, and resort districts. Guides such as Daniel, Chuck, Dino, Deno, and Rae Rae have been praised for lively commentary. The ride lasts about an hour, but check the final departure before booking your hike.

“We had a wonderful time. We picked the last tour of the day. The trade winds were blowing the the driver was entertaining and affable. We just hit a great time. It was perfect. We got to see a lot without having to walk and walk and it just was a great hour and a half for a great price. Very satisfied”

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3.Diamond Head Hike with Roundtrip Transportation

★★★★★★★★★★4.3 · 354 reviews · 3 hours · from $63

Start with a 5:00 to 5:10 AM Waikiki pickup, ride to Diamond Head, and hike independently toward a sunrise view over Waikiki and the Pacific. Entrance fees, roundtrip transport, and gratuities are included. The hike is not guided in English, and the trail is unsuitable for visitors with mobility issues.

“Absolutely gorgeous views when hiking up Diamond Head. Transportation was prompt, clean and well organised. Just a note to say that you are on a tour that is designed for Japanese tourists so there was little information for other languages. Absolutely loved the views :)”

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4.Diamond Head Hiking and Oahu Island Experience feat. North Shore

★★★★★★★★★★5.0 · 319 reviews · 11 hours (approx.) · from $110

Start with an early Diamond Head hike, then ride an air-conditioned van around Oahu’s east and North Shore. You’ll stop at Halona Blowhole, Kualoa, Sunset Beach, Haleiwa, Dole Plantation, and local food stands. Guides such as Stephanie, Jonah, and John add island history and folklore. Lunch and shopping are separate costs.

“Our driver, Allen, was great! I wouldn’t say the tour is unnecessarily long, and we would I have preferred longer time at sunset beach in order to swim rather than stops to stores (macadamia, Dole, fruit stand etc) for us to spend money.”

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5.Diamond Head Hike Shuttle with Reservation Tickets Included

★★★★★★★★★★5.0 · 223 reviews · 2 hours 30 minutes (approx.) · from $39

This self-guided Diamond Head outing includes Waikiki pickup, round-trip transportation, and your state park reservation. Drivers such as Matthew, Matt, and Eric have earned praise for friendly service, local tips, and smooth driving. You hike at your own pace, but expect stairs, uneven ground, heat, and a narrow tunnel before the summit.

“Wonderful hike and Matthew was a terrific guide with a lot of options for us. It was nice to have a ride over to Diamond Head.”

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6.Diamond Head Crater Hike and North Shore Experience

★★★★★★★★★★4.7 · 189 reviews · 10 hours · from $125

Spend 10 hours touring Oahu by air-conditioned van, beginning with a 105-minute Diamond Head hike. With an English-speaking guide such as John, Stephanie, or Jonah, you’ll visit Halona Blowhole, Tropical Farms, Kualoa Regional Park, Kahuku Sugar Mill, North Shore beaches, and Dole Plantation. Hotel pickup, transport, and Diamond Head admission are included.

“So I‘m from Switzerland and always think it‘s funny when they say we are doing a hike - to me it was really a walk. :) But it was soooo worth it to see the sunrise from up there! You will see all the shore-highlights on that day too.. She gave us a couple of minutes everywhere so we could take pictures. You will see really a lot in just one day. It was fun and I would do it again. Mahalo.”

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7.Diamond Head Bike to Hike and Local Lunch

★★★★★★★★★★5.0 · 181 reviews · 4 hours (approx.) · from $159

Start at 7 a.m. in Waikiki with guide Kelly, then ride a provided 7-speed bike past Kapiolani Park, Makalei Beach, Diamond Head Lighthouse, Shangri-La, and Hawaii Five-O studios. After a 1.5-hour crater hike, stop for a local lunch before returning to Waikiki. Expect 9 to 12 miles of cycling, hills, stairs, snacks, water, and photos.

“Getting to the Diamond Head in a different way: bike! Kelly is a great guide, and makes this a super enjoyable experience. You get to know places , you wouldn't pass by in another way. The bikes are great, the trails, hiking and views totally worth it. If you like to bike , you'll have a great time. Also super cool: the pics you get of yourself 🤩🚲🙌! Thanks!”

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8.Electric Bike Ride & Diamond Head Hike Tour

★★★★★★★★★★5.0 · 125 reviews · 3 hours 30 minutes (approx.) · from $199

Start near Waikiki with an English-speaking guide such as Ryan or Dave, ride an e-bike through beach parks and local streets, then hike Diamond Head State Monument. Expect a small group, helmet, included admission, coastal views, history, photo stops, and a moderately strenuous climb.

“Ryan was a great guide! Very attentive on bike ride and hike. We enjoyed all of the photo ops around Waikiki Beach. The hike at Diamond Head State Park had beautiful views at the top so worth the hike. What a great afternoon! Thanks Ryan”

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9.Honolulu: Diamond Head Segway Tour

★★★★★★★★★★5.0 · 37 reviews · 2 hours · from $155

Spend two hours riding a Segway from the Honolulu Zoo around Diamond Head. After hands-on training, your guide leads you past Kapiolani Park, the Waikiki Aquarium, Coconut Avenue, Leahi Beach Park, the lighthouse, Earhart Lookout, and Fort Ruger. English and Japanese guidance is available, including instruction from Timo.

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10.Diamond Head E-bike Scenic Ride

★★★★★★★★★★4.7 · 22 reviews · 1h 30m · from $149

Ride from Waikiki around Diamond Head with a small group of up to six. Your guide leads you past Kapiolani Park, Amelia Earhart Lookout, Kahala Lookout, the Ala Wai Canal, and Kalakaua Avenue. E-bikes handle the hills, while guides Ryan and Ayano add local context and take complimentary photos.

“Absolutely incredible! Our favourite tour we did on the trip. Our tour guide was the most loveliest Man.”

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11.Diamond Head Crater Trailhead Transfer & Entry Fee

★★★★★★★★★★4.5 · 21 reviews · from $50

Ride in an air-conditioned vehicle from Waikiki or Waialae-Kahala to Diamond Head State Monument. You get the admission fee, English-speaking driver, and return transport, then about 105 minutes to hike independently. Bring water, sunscreen, hiking shoes, and a hat. Pickup details arrive one day before departure.

“Super Trail für jedes Alter und wahnsinniger Blick auf die Insel”

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12.Honolulu: Diamond Head Hike with Transfers

★★★★★★★★★★3.2 · 13 reviews · 3 hours · from $75

Ride to Diamond Head with an English or Spanish-speaking driver, then follow the 1.6-mile round-trip trail to Oʻahu’s famous crater summit. You’ll pass lava rock, dryland plants, WWII bunkers, a dim tunnel, steep stairs, and a spiral staircase before reaching broad views of Waikīkī, the Pacific, and the Koʻolau Range. Sergio is one named driver praised for friendly service.

“Loved this! Such a fun day. The hike is fairly steep but totally worth it! Gorgeous views of the city and ocean. I’m glad we did this tour so we didn’t have to worry about hiking reservations or parking. Overall 10/10!”

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13.Parasail on Maunalua Bay with Diamond Head Views

★★★★★★★★★★4.7 · 9 reviews · 1h 30m · from $97

You’ll ride a speedboat from Honolulu to Maunalua Bay, hear a safety briefing, then rise 600 feet above the Pacific for a six-minute solo or tandem flight. Look for Diamond Head, Koko Head, Hawaii Kai, and the Ko’olau Mountains. The captain may dip you into the water before landing. Scotty and Rick are among the crew named in past bookings.

“Amazing staff and great view! Got a dolphin show today on group 8!”

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14.Honolulu E-Bike Ride and Diamond Head Hike

★★★★★★★★★★5.0 · 8 reviews · from $189

Start at Kuhio Village Tower for a guided e-bike ride from Waikiki along the beach and coast to Diamond Head. After locking the bikes, hike about 1.5 miles to the crater summit, with steep stairs and dramatic views. Guides such as Ryan and Dave share local history, take photos, and may finish with optional shaved ice.

“We had a really great time touring the area of Diamond Head with Dave, and then hiking up the crater. It took me a few awkward moments to learn how to ride the E bike, which is quite heavy. But I quickly got the hang of it and it was fine after that. The hike itself is quite strenuous. We are fit people, and it was challenging for me. I would not recommend for people who are out of shape or for families with very young children. The views from the top are spectacular and worth the hike up. Highly recommend!”

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15.Diamond Head Manoa Falls

★★★★★★★★★★5.0 · 5 reviews · 6 hours · from $245

Spend six hours on a private Oahu tour with guide Lucas or another English-speaking guide. Hike Diamond Head for Waikiki views, stop for an optional breakfast, then walk through bamboo forest to Manoa Falls. Admission and hotel pickup are included, while breakfast and gratuity are extra.

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