5.0
(1)
1,806
riders
26
rides
Road cycling around Kailua, located on Oahu's windward coast, offers diverse terrain for cyclists. The region is characterized by coastal areas with ocean views and routes that extend inland towards the Ko'olau Range. These routes feature varied scenery, from flat stretches along the coast to climbs with significant elevation gains. The landscape provides options for different fitness levels, encompassing both scenic, easy rides and more challenging ascents.
Last updated: May 27, 2026
12
riders
41.8km
02:51
1,370m
1,370m
If you are looking for a truly challenging racebike adventure, the Luhia to Kaloko Drive delivers a difficult climb over 26.0 miles (41.8 km). You will gain an impressive 4494…
9
riders
19.3km
00:55
250m
260m
The Hillcrest to Keauhou loop is an easy 12.0-mile (19.3 km) road cycling route that you can complete in about 55 minutes. You will gain 831 feet (253 metres) of…

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490
riders
32.2km
01:19
180m
180m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
418
riders
Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.
133
riders
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Popular around Kailua
Founded in 1820, the church is the oldest church in Hawaii
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small museum in the former summer residence of the royal family
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Breathtaking landscapes, beautiful routes to tackle!
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Aliʻi Drive is one of the most beautiful snorkeling spots along the east coast to the east. A stop here is always worthwhile, as the postcard-famous blue ocean and small St. Peters Catholic Church is located here. The best time to cycle through is early in the morning, but during that time it is important be respectful of the surfers who get up early to surf here.
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There are over 20 road cycling routes around Kailua, offering a variety of experiences from easy coastal rides to challenging climbs into the Ko'olau Range. You'll find options suitable for different fitness levels.
Yes, Kailua offers several easy road cycling routes. For instance, the Hillcrest to Keauhou loop is an easy 12-mile ride with scenic views and moderate elevation gain. The area also features coastal paths like the Kailua Beach Path, perfect for a relaxing ride.
Kailua's road cycling routes offer diverse scenery. You can expect breathtaking ocean views along coastal paths, dramatic backdrops of the Ko'olau Range, and routes that traverse varied inland terrain, including volcanic landscapes. Some routes also pass by famous beaches like Kailua Beach Park and Lanikai Beach.
Absolutely. For those seeking a challenge, routes like Luhia to Kaloko Drive offer substantial elevation gains and traverse varied inland terrain over 26 miles. These routes provide a good workout with rewarding views.
Yes, many of the road cycling routes in Kailua are designed as loops. Examples include the Hillcrest to Keauhou loop and the Bicycle on Balcony – Lava Tube loop from Kailua-Kona, allowing you to start and finish at the same point without retracing your path.
While cycling, you might pass by significant landmarks and natural features. Near Kailua-Kona, you could encounter historical sites like Huliheʻe Palace or the St. Peter's Catholic Church. The scenic coastal routes often provide views of the iconic Mokulua Islands and access to famous beaches like Kailua Beach Park and Lanikai Beach.
The komoot community highly rates the road cycling experience in Kailua, with an average score of 3.0 stars. Cyclists often praise the diverse terrain, from stunning coastal views to challenging inland climbs, and the variety of routes suitable for all abilities.
Yes, some routes offer a unique experience through volcanic landscapes. The Bicycle on Balcony – Lava Tube loop from Kailua-Kona is a notable example, leading you through terrain shaped by the island's volcanic origins.
Route durations vary significantly based on distance and difficulty. Easy routes like the Hillcrest to Keauhou loop can be completed in under an hour, while more challenging routes such as Luhia to Kaloko Drive might take close to three hours.
While primarily focused on natural beauty, some routes in the broader Kailua area may bring you close to cultural or historical points of interest. For example, the Kailua-Kona – Kailua Bay loop from St. Michael the Archangel Parish passes by the historic St. Michael the Archangel Parish.
Kailua's road cycling routes offer a mix of terrain. You'll find flat stretches along the coast, moderate climbs, and significant ascents as routes extend inland towards the Ko'olau Range. The landscape transitions from sandy beaches to lush jungles and volcanic areas.


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