5:00 a.m. Awake at Moon Hill to a still-starry night for a quick breakfast and to review my gear: Tent, check; sub-zero sleeping bag, check; water bottles, check. food provisions, check; wool socks, check; smartwool long underwear, check; down parka, check; hiking companion, check; boots, doh! sneakers will have to do (big mistake).
5:30 a.m. Depart Moon Hill for Mavis Bank, passing through Papine, Gordon Town as day breaks.
7:30 a.m. Park by Jamaica Constabulary Force station in Mavis bank to ensure car is left under watchful eyes, don pack and head out, following road to ford Yallahs River and head up through Hagley Gap, Epping Farm, Penlyne Castle and on to Whitfield Hall.
2:00 p.m. Arrive Whitfield Hall, put down pack to rest after seven hours of strenuous uphill trodding, albeit on the dirt road.
2:30 p.m. After downing some trail mix and a liter of water, we leave the last vestige of civilization behind at Whitfield Hall and make for the trail head.
3:30 p.m. Arrive at Portland Gap and tour the camp site and rustic cabins. Our legs scream, make camp here, but our egos won't allow it. Trod on!
4:30 p.m. Asking hikers heading down the mountain how far we have to go.
4:45 p.m. Asking another hiker happily heading down if we soon reach...
5:30 p.m. We approach the summit, just in time for a spectacular sunset. A birdseye view of Kingston, the harbor and Palisadoes from a perch on top of the world is breathtaking. The Caribbean can be seen in all its splendor to the north, east and south.
6:00 p.m. Sun down, night approaches and we hastily set up the tent and down some grub to prepare for the cold night.
6:30 a.m. Frost on the outside of the tent wakes us with the Sunrise. Brush teeth and greet the day, happy for imminent warmth of the rising sun and moving limbs.
7:00 a.m. After a quick breakfast we begin the journey back down to Mavis Bank.
9:30 a.m. Stop by Whitfield Hall for a quick break. Head back out before legs stiffen and growing pain in my toes takes over.
11:00 a.m. Toes begin throbbing as nails jolt repeatedly against the front of my sneakers as we reach Penlyne Castle. We've opted for an alternate route along the trail down to Mavis Bank, a wise decision, but it doesn't save my toes.
1:00 p.m. Reach the Yallahs River and ford with pack held high.
2:00 p.m. Back at Mavis Bank police station, exhausted, thrilled to throw my pack in the back of the car and head back to civilization, legs trembling, toe nails bleeding, vowing never to attempt such a hike with a 40-pound pack in sneakers.
4:30 p.m. Reach Moon Hill to a welcoming hot shower, beer and rehabilitating dip in the pool, anxious for a hearty, home-cooked meal.