The best running trails around Wailea
4.4
(7)
1,348
runners
50
runs
Last updated: October 4, 2025
115
runners
1. Wailea Oceanfront Boardwalk Trail run — Mākena State Park
5.16km
00:33
30m
30m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
80
runners
2. Charley Young Beach loop run — Wailea
10.5km
01:07
90m
90m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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53
runners
3. Keawakapu Beach Trail loop run — Kihei
11.5km
01:12
120m
120m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.5
(2)
37
runners
4. Wailea Oceanfront Boardwalk Trail loop run — Wailea
4.88km
00:31
40m
40m
Easy run. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
4.5
(2)
30
runners
5. Mākena Road & Wailea Alanui Drive loop run — Wailea
7.01km
00:44
60m
60m
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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