4.4
(5)
156
riders
20
rides
Touring cycling around Wailea, Hawaii, offers diverse landscapes ranging from pristine coastal paths to challenging volcanic terrain. The region is characterized by crescent-shaped beaches, ancient lava flows, and lush inland scenery. Cyclists can explore routes with continuous ocean views, traverse volcanic formations, and encounter varied elevations. This unique blend provides a wide array of experiences for touring cyclists.
Last updated: October 10, 2026
4
riders
11.3km
00:42
90m
90m
Embark on an easy touring bicycle ride through Mākena State Park via Polo Beach, a route that spans 7.1 miles (11.3 km) with a gentle elevation gain of 301 feet…
10.1km
00:41
140m
140m
Enjoy an easy 6.3-mile touring cycling loop along the Wailea coast, featuring beautiful beaches and ocean views.

4.3
(3)
35
riders
48.9km
02:57
250m
250m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
16
riders
18.7km
01:11
170m
170m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
11
riders
18.8km
01:11
170m
170m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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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.
1
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Lots of fresh air and always parallel to the water.
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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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Wailea offers a good selection of touring cycling routes, with over 20 options to explore. These routes cater to various skill levels, from easy coastal rides to more challenging inland adventures.
Wailea's touring cycling routes feature diverse terrain. You'll find pristine coastal paths with continuous ocean views, as well as routes that traverse volcanic formations and lush inland scenery. Some routes, like the Piilani Highway via Ulupalakua, can include significant elevation changes and potentially unpaved or narrow sections, offering a more challenging experience.
Yes, Wailea has several easy and scenic options. The Mākena State Park via Polo Beach route is an easy 7.0-mile ride offering continuous coastal views and passing by beautiful beaches. Another great choice is the Wailea Beach via Keawakapu loop, an easy 6.3-mile path with scenic ocean vistas.
Many routes offer views of Wailea's stunning coastline and beaches. You might pass by Keawakapu Beach or the Wailea Oceanfront Boardwalk. Further afield, you could encounter the dramatic Lava Fields at King's Trailhead or the historic Hanamanioa Lighthouse.
Yes, Wailea offers several excellent loop routes. The Kihei Boat Ramp – Keawakapu Beach loop is a moderate 22.2-mile option, and the Wailea Beach loop from Wailea is a moderate 12.6-mile ride, both providing great opportunities to explore the coastal scenery.
The touring cycling routes in Wailea are highly regarded by the komoot community, with an impressive average rating of 4.75 out of 5 stars from over 5 reviews. Cyclists often praise the continuous ocean views, diverse landscapes, and the variety of experiences available, from leisurely coastal rides to challenging climbs.
Yes, bicycle rentals are readily available across Maui, including in and around Wailea. This makes it convenient for visitors to explore the region's diverse cycling routes without bringing their own equipment.
Wailea generally offers pleasant cycling conditions year-round due to its tropical climate. However, the winter months (December to April) are popular for cooler temperatures and whale watching opportunities along the coast. Always check local weather forecasts before heading out.
Absolutely. For experienced touring cyclists seeking a challenge, the Piilani Highway via Ulupalakua is a difficult 32.4-mile route. It features significant elevation changes and leads through diverse landscapes with ocean views, sometimes including unpaved segments and narrow sections.
Wailea is a well-developed resort area, so you'll find numerous cafes, restaurants, and accommodation options conveniently located near many of the cycling routes and beaches. This makes it easy to refuel or relax after your ride.
Beyond the beautiful beaches, Wailea's natural features include dramatic volcanic formations and ancient lava fields, particularly in areas like La Perouse Bay. You might also catch glimpses of the majestic Haleakalā volcano in the distance, or pass by natural reserves like Keālia Pond National Wildlife Refuge.


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