[All photos courtesy of Nate Christenson and Josh Kurpius.]

When I got the call at 5pm during my treasured Friday happy hour, I told them to book my flight ASAP. The trip sounded like a blast. Embedding with Harley Davidson and Team Mondavi on a 1,400-mile, round-trip ride from Los Angeles to Napa on the West Coast along historic Highway 1 sounded like what was up.

This was the Prohibition Run. Brainchild of wine-country scion Carlo Mondavi and a few of his tight-knit friends. Not for the weary. One part endurance race, two parts Milwaukee steel, three parts drifting cliffs, topped off with a cabernet grape and shaken vigorously into a raging party in Napa. With that in mind, we rolled out of Los Angeles on a mission to tear shit up. 

Leading the pack was Carlo. Grandson of famed wine pioneer Robert Mondavi, and son of award-winning vintner Tim Mondavi, he is Heir to the Throne, no stranger to the wine game. The Mondavi name has been synonymous with making corks pop and panties drop for generations. This family is supremely legit, and it shows in the quality, craft, and credentials of their game. If you don't know, now you know.

The Harley people were gracious enough to lend a baker’s dozen of their trusty steeds to be split up among 15 players. A mix of Cali folk, pro snowboarders, musicians, artists, and hooligans rounded out the crew. No matter how we all began, we all left off with a newfound respect for the road and the wine game.

Night one, we got to know our bikes. Immediately attracted to the StreetGlide, I hopped on and made her my bitch. With the touch of a button, she let off like double-barreled buckshot. Smooth, elegant curves. Sedona Orange paint flickering in the full moon light. Chrome down to the socks. The sexy beast let out a long, raspy baritone note, and we were in love. As I flicked her big body around the Venice night, I could tell she was a pro. Agile enough to split lanes at speed. Saddlebags that would make JLo Jell-o. Anticipating what was to come, I knew this was no disco nap of a ride. I caught my 40 winks.

Full tanks of gas, and we were off. Crisp SoCal air cooled the fins on our engines over to the coast in an harmonic rumble, as 13 bikes in cockeyed centipede formation cut through Santa Monica like so much warm tofu.

Hopping over to Highway 1, we picked up speed through the hills as we made our way to Big Sur for the night. Sweeping mountain crests and low-speed, snaked-out curves led my bike up along the cliffs effortlessly. The new Harley 103 engine put out 102 lb-ft of raw torque to the rear tire. The engine bored out to 3.875 inches left plenty of room on the throttle to chirp it out on Smokey if need be. An 18-inch up front, and a low-slung 16-inch rear fattie kept it in lounge mode. Once relaxed, my fingers were able to tickle the Harman/Kardon system and find some old Dre beats to pump at high speed.

The late start out of Venice had us fighting dark up to the top of Big Sur. Alien landscapes and rugged coastal scenery turned to pumpkin-hued night. I wasn't in the Bronx anymore, and I have to say the last leg along the bottomless cliffs had me checking myself. In the black of night we had ourselves a little adventure finding the hotel. Victory at last had us corking up a few cases of the Mondavi's private stock cabernet sauvignon by the fire. Sweet dreams.

On our way up the coast from Big Sur, beautiful weather gave way to a nasty storm front that ripped into us like a fleet of kamikazee dive-bombers from the Pacific. We geared up best we could and set off to lay down another 300 miles to Napa. Up the hills and freak-show cliffs of Big Sur, we pushed on through driving rain, carving canyons along a backdrop of mystic monster rock formations and roaming livestock, and over to Pebble Beach for a private tour of 17 Mile Drive. Soaked to the core, we stopped through the exclusive Monterey Peninsula Dunes golf course clubhouse and took over the fireplaces like we were hobo's on the Lexington Ave. line seeking heat from exhaust grates. Thirty minutes of heating up our socks, gloves, and jackets by the fire, and it was time to set off again. We hit the road like a freight train through San Fran with one stop in mind—Napa and a bottomless river of red, red wine...

At some point during this leg of the trip, we threw caution to the wind and flipped into Cannonball Run mode. Every man for himself, as we charged forward like something out of a Blues Brothers prequel. Ripping through traffic, lane splitting, and eating small children through the purple rain. Basic riding etiquette had no place here, and it was no holds barred, as we tore past anything that stood in our way. Good thing these bikes had the balls to deliver. They held up to the challenge and gripped the rain-soaked roads to deliver us safe and sound to the Mondavi estate.

What ensued was a feast of epic proportions. We ate and quenched our wine lust like Vikings returning from a hearty conquest. Big ups to the Mondavi boys and their homeys for taking great care of the team. I took myself out like Chuck Norris with extreme prejudice that night and we all lived to tell.

The next day had us kickstands up by 9am and back on the road toward the Ovid Vineyard for a particularly interesting stop. Behind seemingly innocuous gates stood one of the most renowned micro-vineyards in Napa. Each harvest yielding just 500 prized barrels. At $500-$1,000 a bottle for the good stuff, you have to be player status to enjoy. And that's even if you can get your hands on it. Last stop was at the Mondavi brothers’ private operation. Little known, the sons of world-class wine expert Tim Mondavi have been up to their own tricks. What I can tell you is if you can get a hold of the 2007 M Brothers 3 cabernet sauvignon, it is a beautiful thing. Believe me, I did quality testing on more than three cases and the quality, build, and delivery were on par with the greats.

The last night in Napa was one for the ages. Carlo set up a grand finale concert for a few of his boys who were brave enough to come along for the ride. Chris Pierce opened up for Butch Walker & the Black Widows at the Kitchen Door for what turned into a banging party. After forgetting my credit card at the bar, we formed a caravan back into the hills to party till the break of dawn once again.

Leaving Napa in the rearview mirror was such sweet sorrow as we set off on a 700-mile journey back to LA. Hammer down, we booked our asses through daylight on into dusk and through sea foam-scented night back down Highway 1. The night ride had us caught somewhere between mind-numbing zombie and careless fear of the unknown. If you've ever done the cliffs off of Big Sur in pitch black, you know what I speak of...

Rolling into SoCal had us twitching with anticipation. So much to digest. So little brain matter left. Time to get on a flight to NYC and back on the grind. The Prohibition Run, motorcycles, wine, and a double twist of madness.

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