Sometime in the fall of 2008 my buddy Bryan calculated that the way our holidays fell this year, we could get a full two weeks off by taking only 6 days of vacation. I was hesitant… having family and a girlfriend here, I wasn’t sure how that was going to fly. But after some long discussions and and a few hours on a plane, I ended up with this:

Which of course eventually led to this:

Good times were had. With four of us traveling together there was a good amount of concern that we might kill each other after week 1, but we managed to survive. A lot of that is probably due to the commitment to flexibility (read: refusal to plan anything) that ended up working quite well. This strategy also helped us easily absorb travel hiccups, such as me arriving 24 hours prior to them thanks to American Airlines commitment to quality.

We ended up seeing a good part of the island. Basically looked like this:

• 12/22 Flew into Kingston
• 12/22-12/23 Stayed at the Hilton by myself in Kingston drinking red stripe at the pool bar.
• 12/23 My companions arrive, and we drive to Port Maria on the north coast.
• 12/23-12/26 Blue Harbour (some serious Ian Flemming territory)
• 12/26-12/28 Random shitty hotel in Montego Bay
• 12/28-1/1 Spent New Years in an All-Inclusive resort, Riu
• 1/1-1/2 Back at the Hilton winding down and ensuring our bags are suitable for air travel.

I’ve got a few more things to say about Jamaica which I will probably spread across a few posts just to pad it all out. Stay tuned.