4.6
(40)
746
hikers
20
hikes
Hiking around Kailua offers a range of trails primarily characterized by coastal paths and urban loops. The region features relatively flat terrain with minimal elevation gain, making it accessible for various activity levels. These routes often provide views of Kailua Bay and pass through local points of interest. The landscape is defined by its proximity to the ocean and developed areas.
Last updated: April 27, 2026
46
hikers
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
5.0
(3)
28
hikers
2.69km
00:42
20m
20m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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15
hikers
8.63km
02:18
90m
90m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
13
hikers
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
13
hikers
1.25km
00:19
10m
10m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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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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Come see the beaches of Kona and enjoy the renowned coffee, ride the same course as professional triathletes, and kick back at one of the many restaurants available within pedaling distance!
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In 1924 this historic building was in ruins and dilapidated. Like much of the low income housing in the midwest, this property could not even be seen from the road. The property was owned by the Daughters of the Territorial Legislature and even after pressure to sell the valuable land the building was on, they held strong and eventually the building was restored many years later. Inside, there are old artifacts and furniture to show Hawai‘i's royal past.
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Ali‘i Garden Marketplace is a great stop on a ride to grab a bite from one of the 20+ vendors available in this open-air market. In addition to food, there is plenty of shopping and free wifi!
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This beautiful spot is perhaps best known as the starting point for the grueling swimming portion of the annual IRONMAN World Championship triathlon. When not hosting this iconic sporting event, Kailua Bay dazzles with its postcard-worthy scenery. Whether you're a triathlete or a leisurely runner, you'll enjoy running along this charming bay nestled on the sunny shores of paradise.
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Kailua offers a variety of trails, primarily characterized by coastal paths and urban loops. The terrain is generally flat with minimal elevation gain, making it accessible for many activity levels. You'll find routes that provide views of Kailua Bay and pass through local points of interest.
There are 18 hiking routes available in Kailua, with 14 rated as easy and 4 as moderate. There are no difficult trails listed, making the area suitable for a wide range of hikers.
Yes, Kailua is well-suited for family-friendly and easy hikes. Most of the trails are rated as easy, such as the Mokuaikaua Church – Kailua-Kona loop from St. Michael the Archangel Parish, which offers a pleasant walk along the bay and through historical areas. These routes are generally flat and accessible.
While Kailua's immediate trails focus on coastal and urban views, the broader Oahu region is known for stunning natural features. For panoramic ocean views, the famous Lanikai Pillbox Hike (Kaiwa Ridge Trail) is a highlight. For lush rainforests and waterfalls, consider the Maunawili Falls Trail. These offer diverse natural experiences beyond the immediate Kailua urban paths.
The hiking routes in Kailua are highly rated by the komoot community, with an average score of 4.5 stars from over 30 reviews. Hikers often praise the accessible coastal views and the opportunity to explore historical areas within the town.
Yes, many of the routes in Kailua are designed as loops. For instance, the Kailua-Kona – Mokuaikaua Church loop from Puapuaʻa Point is a moderate 8.6 km trail that takes you through coastal views and the town center, returning to your starting point.
Several trails in Kailua pass by significant landmarks. You can explore sites like the Huliheʻe Palace, a former vacation home for Hawaiian royalty, or the historic St. Peter's Catholic Church. The routes often weave through the Kailua-Kona settlement itself, offering a glimpse into its rich history.
While the immediate Kailua trails are more coastal and urban, the broader Oahu region offers such experiences. The Maunawili Falls Trail, for example, provides a trek through a lush rainforest culminating in a picturesque waterfall and natural swimming hole, offering a deeper immersion into Hawaii's natural landscapes.
Kailua, located on the windward side of Oahu, generally offers pleasant hiking conditions year-round due to Hawaii's tropical climate. However, the cooler, drier months from April to October are often preferred for outdoor activities, avoiding the slightly wetter winter season.
For more experienced adventurers seeking a challenge, the Olomana Three Peaks Trail, often called the 'Everest of Kailua,' is a strenuous and technical hike offering breathtaking 360-degree views of the Windward coast and the Ko'olau Range. This is a significant step up from the moderate trails found directly within Kailua.
Yes, for a tranquil experience and excellent birdwatching opportunities, the Kawainui Marsh Trail is a flat, approximately 3-mile path through Hawaii's largest wetland. It offers striking windward mountain views and is a haven for four endangered native Hawaiian waterbirds.
Yes, the iconic Lanikai Pillbox Hike (Kaiwa Ridge Trail), though relatively short, is famous for its spectacular sunrise views over the Mokulua Islands. It's a popular choice for those seeking stunning coastal vistas.


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