Diamond Head Tours: The 15 Easiest Ways Up the Crater

1.Diamond Head Crater

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

Ride from Waikiki to Diamond Head for a self-guided hike with park entry, a trail map, and bottled water included. You set your pace on the 1.6-mile route, passing through old military tunnels and climbing steep steps near the 760-foot summit. Drivers such as Matthew, Tommy, and Orlando have shared island tips on the ride.

“This was the third time I climbed diamond head and it is a to do while in Waikīkī. Seemed like more stairs than the last time but also 7 years later so a little older. Lol”

Check availability →Read our full review

2.Waikiki Trolley Green Line Diamond Head Shuttle

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

Take E Noa Tours’ Green Line trolley from Waikiki toward Diamond Head, KCC Farmers’ Market on Saturdays, and Kahala Lookout. The roughly one-hour ride passes the Duke Kahanamoku Statue and Kapiolani Regional Park. Drivers such as Daniel, Chuck, and Rae Rae have been praised for lively commentary, but check the final departure time and buy any Diamond Head trail pass separately.

“The tour guide was very informative and accommodating. Great personality. I was travelling solo and he offered to take pics of me. Too bad I forgot his name. I would've liked more instructions on where exactly to get the trolley. Was told Ikiliaka hotel, didnt see any signs posted. Almost missed it. Thanks again to the driver...think his name is Jerry?”

Check availability →Read our full review

3.Diamond Head Hike with Roundtrip Transportation

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

Start with a 5:00 to 5:10 AM pickup at a designated Waikiki point, ride to Diamond Head and hike the summit trail on your own. Entrance fees and roundtrip transport are included. You can catch the early light and panoramic views, but expect limited English commentary on some departures and no hiking guide on the trail.

“If you're looking for an adrenaline rush and a breathtaking view, you should definitely do this tour! The guide Jun picked me up and dropped me off on time. He was not only an experienced hiker but also a great motivator and running partner! Together we stormed the summit and were rewarded with an unforgettable sunrise. I was the first to enjoy the sunrise over the mountains! Thanks to Jun! I definitely come back. 💪🏼🤙🏼 Greetings, Linh”

Check availability →Read our full review

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

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

Start early with the steep Diamond Head hike, then ride an air-conditioned van around Oahu’s east coast and North Shore. Stops include Halona Blowhole, a macadamia nut farm, Kahuku food trucks, Sunset Beach, Haleiwa, and Dole Plantation. Guides such as Stephanie and Jonah are praised for island stories and a flexible, friendly approach.

“Our driver, Stephanie, did a great job showing us many sights and giving us some history. The food truck area was great and delicious. We had the perfect amount of time at each stop.”

Check availability →Read our full review

5.Diamond Head Hike Shuttle with Reservation Tickets Included

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

This Waikiki shuttle takes you to Diamond Head with a park reservation ticket included, then gives you time to hike independently. Expect a scenic drive, a steep trail with stairs and a short tunnel, and wide views from the summit. Drivers such as Matthew and Matt share local context, though the level of commentary can vary.

“Matthew was great, He was a wealth of information and willing to answer any questions we had. I really appreciate how informative, professional and friendly he was!”

Check availability →Read our full review

6.Diamond Head Official Self-Guided Narrated Audio Tour

★★★★★★★★★★3.0 · 212 reviews · 1 to 3 hours (approx.) · from $8Best value

Walk Diamond Head’s 1.6-mile summit trail with a self-guided audio tour covering Hawaiian traditions, military history, geology, plants, and wildlife. You get a digital guide, earphones, and a four-color map, plus help setting up the audio. The $8.99 tour does not include the park reservation, entry fee, or parking.

“Me and my grandson decided to do it and definitely worth the hike.He took a couple of breaks but eventually made to the top and what a view loved it so beautiful from the top.”

Check availability →Read our full review

7.Diamond Head Crater Hike and North Shore Experience

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

Spend 10 hours exploring Oahu by air-conditioned van, with hotel pickup, a 105-minute Diamond Head hike, coastal stops, a Kahuku food-truck lunch break, and Dole Plantation. Your English-speaking driver shares local history and island tips. Guides such as John, Jonah, and Stephanie have been praised, though your guide may differ.

“Absolutely amazing experience! Our guide was phenomenal! Definitely recommend this to anyone! Pickup was easy, directly from our hotel and our guide was so knowledgeable, had great energy and gave us a day to remember.”

Check availability →Read our full review

8.Diamond Head Bike to Hike and Local Lunch

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

Ride 9 to 12 miles from Waikiki toward Diamond Head on a provided 7-speed bicycle, with a local guide, helmet, water, snacks, and photos. Stops include Kapiolani Park, a small beach with green olivine crystals, and the Diamond Head Lighthouse Lookout. Then hike to the crater summit and stop for lunch before returning to Waikiki.

“We enjoyed this tour very much. Our guide Kelly was a plethora of information on the bike tour and hike. It was a great day of exercise and natures beauty.”

Check availability →Read our full review

9.Waikiki and Diamond Head Parasailing Experience

★★★★★★★★★★5.0 · 168 reviews · 1 hour (approx.) · from $34

Take a one-hour shared boat ride off Waikiki, then fly in a tandem or triple harness for up to eight minutes above the ocean. Choose a line length advertised up to 1,000 feet and look back toward Honolulu and Diamond Head. No experience is needed, and crew members such as Kyle, Sundance, Marty, and Lieutenant Dan have helped keep the ride lively and reassuring.

“Amazing time with Kyle very funny and professional, and LT Dan was an amazing pilot made for an awesome experience”

Check availability →Read our full review

10.Electric Bike Ride & Diamond Head Hike Tour

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

Ride an electric bike from Waikiki toward Diamond Head, pausing for local sights and a coastal beach park before hiking to the crater rim. Guides such as Ryan and Dave share island history, help with the bikes and often take photos along the way. The ride is followed by a steep, rewarding hike, so bring water, sunscreen and closed-toe shoes.

“Ryan and Ayano are the best tour guides! We had so much fun riding the e-bikes. They are very personable and knowledgeable about Waikiki and diamond head. Definitely recommend 808eventures!!”

Check availability →Read our full review

11.Diamond Head Hiking Tour with Ticket and Reservation Inclusion

★★★★★★★★★★4.5 · 103 reviews · 3 hours (approx.) · from $50

This 5:30 a.m. outing pairs pickup with a reserved entry to Diamond Head State Monument and time to hike its 1.5-mile trail. Expect switchbacks, stairs, a tunnel, and broad views over Waikīkī and the Pacific. Drivers such as Jonah and Johnna have shared local history and food tips on the ride; the hike itself is independent.

“This was such a great way to enjoy the Diamond Head trail early in the morning. Easy transportation back and forth from Waikiki. We got there right when the park opened. Our driver Jon made sure we had water and flashlights for when we needed them!”

Check availability →Read our full review

12.1-Hour Diamond Head Sail of Waikiki Beach

★★★★★★★★★★5.0 · 56 reviews · 1 hour (approx.) · from $52

Ke Kai Catamaran takes you from Waikiki Beach into Mamala Bay for an hour of coastline views, music, and complimentary drinks. Expect a casual sail with a friendly crew and a close look at Diamond Head from the water. Crew members named on past trips include Kyle, Jesse, Nick, Brandon, Justin, Alek, and Aidan, though staffing can vary.

“The crew was fun and very welcoming. The drinks were good and the views spectacular. Definitely a must do while in Oahu”

Check availability →Read our full review

13.Diamond Head Electric Bike Scenic Tour

★★★★★★★★★★5.0 · 47 reviews · 2 hours (approx.) · from $149

Set out from Waikiki with a guide such as Ryan or Dave for a roughly two-hour e-bike ride past Kapiolani Park, coastal viewpoints and Diamond Head. You’ll get time to practise before riding, stop for views and photos, and return via the Ala Wai Canal and Kalakaua Avenue. The tour does not include a hike to the crater summit.

“Ryan is a great tour guide, he worked around our HNL layover to make the tour work for our schedule. His shop is less than 30min from the airport, so very doable on a layover. The tour itself was about 2 hours. Very friendly and knowledgeable.”

Check availability →Read our full review

14.Diamond Head Sunrise Hike with Acai Bowl and Malasada

★★★★★★★★★★4.4 · 44 reviews · 4 hours · from $99

Start before dawn with hotel pickup and a climb up Diamond Head, where you can watch sunrise over Waikiki and take in 360-degree views. The four-hour outing includes park entry, a mini acai bowl at Bogart’s Cafe, a malasada, and return transport. A driver speaks English or Japanese; a tour guide is not included.

“The hike was incredible! My husband and I did this as part of our 20-year wedding anniversary trip. The views and sunrise were stunningThe Malasadas and açaí bowls - absolutely delicious! Our driver was great and everyone was so nice. I definitely recommend!”

Check availability →Read our full review

15.Diamond Head Segway Tour

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

Start outside the Honolulu Zoo for Segway training, then follow a small-group route past Kapiolani Park, historic Coconut Avenue homes, Leahi Beach Park, the lighthouse and coastal lookout points. Sidewalk Surfing Tours guides, including Japanese-speaking instructor Timo, share local history along the way.

Check availability →Read our full review