How to hike Mount Olomana - GrindTV. 770 Auloa Road, Kailua. Take the Pali thru the Kalanionaole Highway and look for the Luana Hills Country Club. Park outside of the club; the entrance to the hike is just a quarter mile. The first two peaks are mildly challenging so be prepared to deal with some dropoffs and climbing up rocks. The first peak offers the highest views, third peak is most challenging. The hike offers unforgettable views of the city. Bring snacks and water for a picnic.