Many have hiked the three peaks of Olomana but few have hiked around the peaks. I did this hike on 2 November 2020 with Bob Tyson. We started at 9 a.m. at the head of the Ohana Bike Trail (OBT) on Old Kalanianaole (pictured below and as green star on the map above).
We hiked the OBT only for a couple minutes, if that, and then headed left on an obscure trail that led us to a dry gulch that sits between the OBT and the Hawaii Youth Correctional Facility. We hiked a ribbon-marked "trail" in the gulch and then left the gulch to ascend briefly to a water tank (see map below).
We passed to the left of the tank and then commenced a climb of a ridge we named after fellow hiker Ed Mersino (hence Mersino Ridge). We then came upon a point on the ridge that intersected with the Olomana Alo trail (created by Joe Bussen). Courtesy of Joe, there is even a sign there.
At that point, instead of beginning the climb of ORT to Peak 1, we instead hiked down ORT toward its start point.
Well before reaching the golf course road where the ORT commences, we veered left at an obscure junction to begin hiking a route called Olomana Express (tbh, we got off track while searching for O Express, as evidenced by forked lines on the map).
We eventually found Point C and commenced the hike of Olomana Express, which was in hikeable condition thanks to recent work by HTMC trail clearers. Note that OE is not often hiked and could have become overgrown in the time after our hike.
Olomana Express eventually connected to Old Government Road (map point D), which we veered left on to begin ascending to the crest of Anianinui Ridge (if we had veered right on OGC, we would have come out on the Royal Hawaiian Golf Course).
The way was clear and open thanks to the work and riding of mountain bikers. About halfway up the grinding climb, we left the mountain bike trail and followed a much less used trail that crested atop Anianinui. This route is called Olomana Hope (pronounced Ho-Pay).
Bob (pictured below) and I took a lengthy rest break once we had topped out on Anianinui. We were glad that most of the climbing for the day was almost complete.
After our rest, we continued up Anianinui toward the backside of Olomana's 3rd peak. 
Before reaching the peak (see above), we veered right on a trail used most recently by mountain bikers that descended to the Ohana Bike Trail at junction they call Renegade (Map point E).
The rest of the hike went quickly at that point and Bob and I completed the 6.75 mile circumnavigation before 2 p.m. (so 4:48:50 according to GAIA GPS which I used to track our route).
