09/17/2009 05:12 am ET Updated Nov 17, 2011

Your Black Leather Chaps Are Freaking Me Out, but the Rest of Your Bucket List Trip Looks Great

My sixty-something father is on a motorcycle trip around the country, on his way to the greatest mother of all motorcycle gatherings, Sturgis. I know, I thought the same thing, "Isn't that the humongous gathering of a million bikers?" Yep, black mountains and big sky country, Harley's, Hells Angels, hot biker women, heaps of hairy men and for God's sake, just thousands of good solid American made people, blaring Kid Rock's Anthem "American Bad A**." It has all the makings of a Pro America ad campaign, or at least a few scenes out of my secret favorite TV guilty pleasure, Sons Of Anarchy.

For the past few weeks leading up to his departure I have officially referred to this shenanigan as "The Bucket List" Trip or the "Old man's trip" but, now that he's on the open road logging three hundred miles a day, truthfully, I am pumped for him. My father has lived in Guam and Hawaii for over 45 years (also known as "the rock") you can drive around the island twice and never fill up the gas tank. There isn't much open road and the usual day in and day out looks like an average episode of Magnum PI; a little surf, some bronzing, a few rounds of golf or fishing in between work days (yeah, I know he lives a tough life) so this is truly a once in a lifetime, serious man trip.

My dad is actually the hardest working guy I know, he has always run his own businesses, and done well. His brain spirals 24/7, he never shuts down. So, it's actually a miracle that he tossed his board shorts and slippers aside, and left the daily island grind behind to strap on some black leather chaps (yes I said leather chaps!) a biker jacket, and steel toe boots to hit the open road with his "boys."

On day one dad filed photos from the road on his iPhone -- I should be honest and mention this first photo featuring him wearing full on black leather chaps (and seemingly proud of it) practically put me into cardiac arrest; I considered booking a flight to intercept the madness immediately! But, once I accepted or at least convinced myself this was just dad playing "dress up" for a week with his buddies, my thinking slid into "wow this is whole maturing thing is not so bad... " Kicking it with your peeps, wearing tacky threads you would never really wear ever at home (ever), driving a fully loaded Harley and knocking back some ice cold Bud in the middle of God Damn America, is really what life is all about at the end of the day isn't it?

This high-octane bromance gathering includes a colorful cast of characters: a Governor, a judge, a pediatric dentist, an entrepreneur and their perspective brothers. It's just screaming Oprah segment, don't even think I didn't consider pitching it. Clear the highways folks, a true band of brother's is rolling into town... the man crushing will be elevated to level twenty.

As I received daily photos from the open road, I started to think that in a little corner of their souls, they all think they're some hot, sexy badass outlaw, channeling their inner Peter Fonda, and Dennis Hopper a la Easy Rider. I mean that's the best part of any road trip right? Changing your name, telling lies, wearing clothes you wouldn't wear at home, and pretending to be a tiny bit of someone else for a few days? At least that's pretty much how all my previous road trips to Vegas seemed to have played out.

I hate to break it to the bad boys of summer '09, but outlaws don't really phone home. A true outlaw wouldn't have an ipod or a digital camera, and certainly there would be some rule against filing emails with a Sent from my iPhone end tag, right? Aw, hell with it, that way of thinking is so 1970. Thank goodness my dad is tech savvy, otherwise I would be missing out on the daily road chronicles I have grown to love and anticipate with both excitement and envy:

"We are off to Sturgis this morning (staying at a friends house in Rapid City SD) having a blast. Did you get any of my photos today?" Love, Dad

"We are now in Montana entering the West Entrance to Yellowstone. 

"I've already put 2,000 miles on my new bike. Jim is 72 and walks with 
a cane and is am inspiration to all of us. Call you later, love dad

"Yesterday we were at another entrance. We stayed the night before in 
Wyoming. I awakened
at this real near log cabin lodge to some deer at 
our back door and moose down the road..."

Did my father just write that he is surrounded by log cabins, deer and moose? Wow, the island boys are definitely off "the rock." Sure, the whole black leather chaps thing is just crazy, if not concerning, but the fact that this group of men from the farthest island you can imagine are experiencing a slice of true Americana is well, just badass.

This whole getting older, bucket list thing doesn't seem like that bad of an idea, let's face it, sixty-seven is really not that far from forty-one now is it?

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