Originally I planned on doing this unsupported, but I'm very glad I was talked into some help. This was a fairly tough course, mainly because of the heat. But also because there's a lot of traffic on the roads on the West and South coast and there's barely any sidewalks. Then on the east coast it's a rollercoaster of hills. And if all that doesn't stress you out, at night there's a lot of dogs protecting houses but also quite a few stray dogs. I ran the east coast carrying a big stick. But was also very grateful to have a crew car fairly near by at all times.
I did this at night to avoid the heat and also to be able to see car lights, and to light myself up so cars could see me. But it's still very hot and it looked more like I swam the first 5 miles, as I was completely drenched in sweat after the first hour.
Once you get past Sam Lords Castle, there's basically no shops or gas stations until you've gone all the way up the east coast, over the top and down to Speightstown. And that took me a good 8 or 9 hours. So that's another reason why crew is a good idea for this run.
Unlike the map of the route I was going to follow, there is one section where I avoided a big hill and an extra km in favor of going along the coast at Bathsheba. And at the very north of the island there are roads on googlemaps which don't exist any more in the real world. So, be careful not to get lost up there.
This is a fun run or hike. For a good runner they could probably do it in under 12 hours easy. And then they would avoid what happened to me, which was getting cooked alive by the sun as I came down the last 10 miles of the west coast.
I started at sunset, which is 6pm. And finished at 11am the next day, in 17 hours and 6 mins. I thought I would do it in 15, but the heat just got the better of me. I look forward to seeing someone else do this fast and better. Good luck!