4.3
(36)
426
riders
7
rides
No traffic touring cycling routes in Diamond Head State Monument feature a distinctive volcanic landscape, including an extinct tuff cone that defines a significant portion of Oʻahu's skyline. The area offers coastal routes with panoramic views of the Pacific Ocean, Honolulu, and Waikiki. Cycling routes often traverse urban and coastal areas, providing scenic rides past landmarks and along paved roads. While the monument itself features a challenging hike, the surrounding roads are well-suited for touring cycling, with some routes including significant elevation gains.
Last updated: July 9, 2026
4
riders
10.2km
00:42
140m
140m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
8.69km
00:33
80m
80m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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5.0
(1)
2
riders
10.2km
00:54
340m
340m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3.0
(1)
13
riders
14.6km
01:19
560m
560m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
31
riders
35.0km
02:43
910m
910m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Diamond Head State Monument
Measuring in at almost 500 acres, this state monument produces truly mind-blowing views out across the water and over Waikiki. Unless you are a Hawai'i resident with a Hawai'i ID, you must make reservations to enter the monument, for a small fee: https://gostateparks.hawaii.gov/diamondhead Diamond Head State Monument is only open from 6am-6pm, with the last hike starting at 4pm. Often, going earlier in the day means fewer crowds.
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Be sure to make a reservation in advance. Stairs also have to be managed. The view makes up for it
1
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Great views of Honolulu and Waikiki Beach
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1
The entrance to the park can be reached from Waikiki in about 15 minutes by public bus (The Bus - e.g. # 2, 23). One way 3$ as of Oct 2023.
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Waioli offers breakfast, lunch, and a variety of pastries. The building has a large patio for outdoor seating, or you can opt to sit indoors and enjoy the historic tea room. They do add a 3% "training fee" to orders (which they will remove upon request). The fee basically offsets their expenses to train staff, which seems like a ordinary business overhead cost, but why not pawn it off on unsuspecting tourists?! Weird fees, but good food.
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Waioli offers breakfast, lunch, and a variety of pastries. The building has a large patio for outdoor seating, or you can opt to sit indoors and enjoy the historic tea room. They do add a 3% "training fee" to orders (which they will remove upon request). The fee basically offsets their expenses to train staff, which seems like a ordinary business overhead cost, but why not pawn it off on unsuspecting tourists?! Weird fees, but good food.
0
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Tantalus Drive leads up to one of, if not the, best lookouts in O'ahu! There is a huge lawn you can roll a picnic rug out on and watch as the sun goes down over Diamond Head Crater and the entire Waikiki region. If you biked up here, this is a great resting spot before you get to enjoy the fun, twisty descent back into town!
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There are 7 dedicated no traffic touring cycling routes in and around Diamond Head State Monument. These routes offer a range of experiences, from easy coastal rides to more challenging climbs.
For those seeking an easier ride, routes like the Diamond Head via Kalākaua Avenue loop and the University of Hawaii to Waioli Kitchen loop are excellent choices. These routes are generally well-paved and offer gentle gradients, making them suitable for all fitness levels.
Yes, experienced cyclists looking for a challenge can tackle routes such as Tantalus via Tantalus Drive or the extensive Tantalus Lookout – Round Top Drive loop from Mānoa. These routes feature significant elevation gains and offer rewarding panoramic views.
Many routes offer stunning coastal views and vistas of the Honolulu skyline and Waikiki. Notable viewpoints include the Kahala Lookout and the Amelia Earhart Marker Lookout. From higher elevations, you can even spot neighboring islands on clear days.
Yes, several routes are family-friendly, especially the easier, well-paved coastal sections. The Diamond Head via Kalākaua Avenue loop is a good option for families, offering relatively flat terrain and scenic surroundings without heavy car traffic.
The area is highly rated by the komoot community, with an average score of 4.3 stars from 36 ratings. Reviewers often praise the stunning coastal scenery, the well-maintained paved paths, and the unique experience of cycling around such an iconic natural landmark.
Yes, many of the touring cycling routes around Diamond Head State Monument are designed as loops, allowing you to start and end at the same point. Examples include the Diamond Head via Kalākaua Avenue loop and the longer Tantalus Lookout – Round Top Drive loop from Mānoa.
Beyond the cycling itself, you can visit the iconic Diamond Head State Monument. Along the coastal routes, you'll pass by landmarks like the historic Diamond Head Lighthouse, Kapiolani Park, and the Waikiki Aquarium. The Fort Ruger Pathway also offers a paved, multi-purpose option.
Diamond Head State Monument is accessible by public transport, particularly TheBus, which has stops near the monument's entrance. This makes it convenient to reach the starting points of many cycling routes without needing a car.
Oʻahu generally enjoys pleasant weather year-round, making touring cycling enjoyable in any season. However, the cooler, drier months from November to May are often preferred for outdoor activities, offering comfortable temperatures and less humidity.
The areas surrounding Diamond Head, particularly towards Waikiki and Kaimuki, offer numerous cafes, restaurants, and convenience stores where you can refuel. Many cyclists incorporate stops into their rides, especially along routes that pass through urban fringes.
While the paved roads leading to the monument and around its base are excellent for touring cycling, the Diamond Head Summit Trail within the crater is a hiking-only trail and does not permit bicycles. Cyclists typically park their bikes at the base and then hike to the summit.


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