4.3
(13)
1,633
riders
13
rides
Road cycling around Wailea offers a diverse landscape characterized by scenic coastal roads and varied inland terrain. The region features routes that traverse volcanic formations and lava fields, providing unique backdrops for rides. Cyclists can experience a range of elevations, from flat, well-paved coastal stretches to more challenging climbs into the island's interior. This combination of ocean views, volcanic geology, and lush scenery defines the road cycling experience in Wailea.
Last updated: April 24, 2026
5.0
(1)
39
riders
97.7km
04:36
1,220m
1,230m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
101
riders
31.6km
01:36
280m
290m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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91
riders
25.5km
01:16
240m
250m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
52
riders
31.6km
01:25
200m
200m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
23
riders
87.3km
03:52
750m
750m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Wailea
Perfect barefoot running beach, as always as early or late in the day as possible.
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Perfect running route for a lap without shoes.
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Lots of fresh air and always parallel to the water.
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Ulua Beach Park is a 0.25-mile-long sandy beach known for its excellent swimming, boogie boarding, and beginner to intermediate snorkeling opportunities, with the rocky outcrop on the north end of the beach offering some of the best spots. Ulua Beach is more crowded than its neighboring beach to the north. The beach gets its name from a famous Hawaiian game fish and was initially called "Kaula'uo" by locals before World War II. It was renamed "Little Tarawa" by US Marines during their training mission, which is still the name some locals use. Limited parking is available, so plan to come early if you need a space.
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Kamaole III is one of the last main beaches in Kilhe and is a favorite hangout for locals and visitors. It includes a giant beach park, playground and barbecue facilities, perfect for families to enjoy a full day enjoying the beach. Sunset here is something of a tradition. Locals make this place a habit in the evenings to play bocce ball, eat and watch the sun go down.
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The Shops at Wailea is a collection of island restaurants and distinctive Hawai‘ian stores. There is a lovely courtyard here where you can enjoy a refreshing drink after your run or pick up any essentials you may need for an afternoon at the beach.
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This beach is a beautiful, small stretch of sand with lots of character. It is named after a nearby resident who became a local celebrity for offering beachgoers a hose to wash the sand off their feet after a swim and keeping the pathways clear past his home. There are plenty of opportunities for snorkeling here and a grassy area for families to enjoy a picnic and beach volleyball on a broader section of the sand. While passing by, watch for sea turtles often spotted in this area. After a run, it is an excellent spot to kick off your shoes and enjoy the scenery.
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Keawakapu I Beach is a serene and tranquil destination situated behind luxurious multi-million dollar homes. It is a popular spot for those who want to enjoy a peaceful and less crowded beach experience. Visitors can indulge in activities such as yoga, jogging, whale watching, walking their furry friends, or just taking in the stunning sunset views. The name 'Keawakapu' means "forbidden cove" due to the intense storms that can hit the beach. Sometimes, after a storm, the sand may be swept away, revealing lava rock. However, over time, the sand returns gradually, thanks to Mother Nature.
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There are over 25 road cycling routes around Wailea, offering a diverse range of experiences. These include 9 easy routes, 12 moderate routes, and 7 more challenging options for experienced riders.
Road cycling in Wailea offers a mix of stunning landscapes. You'll find scenic coastal roads with breathtaking ocean views, routes that traverse unique volcanic formations and lava fields, and diverse elevations ranging from flat, well-paved stretches to challenging climbs into the island's interior. This combination provides varied backdrops for your rides.
Yes, Wailea offers several easy road cycling routes perfect for beginners or those looking for a relaxed ride. An excellent option is Ahihi Bay via Kihei Frontage Road — Maui, which is 18.1 miles long and offers coastal views on mostly well-paved surfaces. Another easy choice is the Mākena State Park – Keawakapu Beach loop, which is about 24 miles long.
For experienced cyclists seeking a challenge, Wailea and its surroundings offer routes with significant elevation changes. The Mokulele Bike Path & Kahekili Highway loop — Maui is a difficult 60.7-mile trail that leads through varied terrain. The broader Maui area also includes formidable climbs like the Haleakalā Summit Ride, which presents over 10,000 feet of elevation gain.
Many road cycling routes in Wailea offer stunning views and pass by notable landmarks. You can cycle past the unique Lava Fields at King's Trailhead, enjoy the coastal beauty of Keawakapu Beach, or ride along the Wailea Oceanfront Boardwalk. Routes often provide constant ocean vistas and opportunities to see lush scenery.
The road cycling experience in Wailea is highly rated by the komoot community, with an average score of 4.4 stars from over 10 reviews. Cyclists often praise the diverse scenery, from breathtaking coastal views to unique volcanic landscapes, and the variety of routes catering to different fitness levels.
Wailea offers good road cycling conditions year-round, but morning rides are generally recommended due to afternoon trade winds. While Maui does have a rainy season (typically November to March) and a hurricane season (June to November), many days remain suitable for cycling. Always check local weather forecasts before heading out.
Yes, Wailea has options suitable for families, particularly those looking for easier, mostly flat rides. Routes like the Ahihi Bay via Kihei Frontage Road — Maui or the Wailea Beach via Keawakapu Loop (approximately 6.3 miles) are excellent choices with well-paved surfaces and minimal elevation, making them enjoyable for all skill levels.
While many road cycling routes in Wailea are on public roads, it's important to check local regulations regarding dogs on specific paths or in natural areas. Generally, dogs are not permitted on multi-use paths like the Wailea Beach Path or in protected natural reserves. Always keep your dog on a leash where permitted and ensure they are comfortable with the pace and environment of a road cycling route.
Parking availability varies by route. For coastal rides, you can often find public parking lots near beaches or parks in areas like Kihei and Wailea. For routes that start further inland, look for designated parking areas at trailheads or community centers. It's advisable to research specific starting points for your chosen route to confirm parking options.
Yes, many road cycling routes in Wailea pass through or near towns and commercial areas where you can find cafes, restaurants, and convenience stores. Coastal routes, in particular, often have easy access to amenities in Kihei and Wailea. For longer inland rides, it's always a good idea to carry sufficient water and snacks, as refreshment stops may be less frequent.
Maui's public bus system, Maui Bus, does offer limited services that can accommodate bicycles, typically on racks at the front of the bus. However, space is often limited, and specific routes or times might have restrictions. It's best to check the official Maui Bus website or contact them directly for the most current information on routes and bike policies relevant to Wailea.
Generally, no specific permits are required for road cycling on public roads in the Wailea area. However, if your route takes you through certain state parks, national parks (like Haleakalā National Park), or private lands, there might be entrance fees or specific regulations. Always check the requirements for any protected areas your chosen route might traverse.


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