I will admit that I have always been envious of those who go on vacation and, upon returning a week later, look relaxed and recharged. I, on the other hand, resemble a large jet plane with half of its landing gear smashed to bits attempting to hit the runway without completely bursting into flames, skidding and spinning for a solid half-mile before careening to a screeching halt, five feet away from a large crowd of civilians. In this regard, I suppose that I would more accurately label a “vacation” as a “quest for oblivion.”

Of course, as far as anyone in a management role at my former company was concerned, my recent excursion to San Francisco was, technically, “for work.” However, when one is in the trade of peddling alcohol for a living, the fine line between business and pleasure is barely existent, to the point where it would be impolite not to partake excessively (so long as one continues to hold it together in public). This is how I justify my life on a day-to-day basis anyway.

To reward my diligence in moving a goodly amount of their product, one of the New Zealand wineries that I represent has invited me to be their guest aboard various boats to witness the spectacle that is the Louis Vuitton Cup segment of the America’s Cup races. Though I know very little about sailboat racing, I do know that I am rather partial to drinking on boats, especially in a city that I am told is like being in “perpetual Autumn.” In my mind this translates into the ultimate fat guy weather, consistently between 60 and 70 degrees and completely lacking in the dreaded humidity that has made my summer in Boston so utterly unbearable. No other kind of climate could be more perfect for both thinking AND drinking.

The Journey

Here is my problem with airlines like Virgin America and Jet Blue:

I’m not sure who it was that made the assumption that most airline passengers, many of whom have anxiety about flying, would ever take a shine to “cool” young ticketing agents with a nonchalant attitude bordering on rude, who ring you up for your luggage check-in the same way you would imagine a 7-11 cashier ringing up a pack of butts. The woman checking me in, between exhaustive hauls off of her jumbo Coolatta, tells me to enjoy my flight as she tosses my boarding pass at me as if it were a subway token.

While awaiting instructions as to which groups are currently boarding the aircraft, the man on the intercom decides it would be utterly fucking hilarious to start throwing in a bit of shtick.

“We are now boarding anyone in section D, as in ‘Dude we are finally going to get out of here!”

He is not done. When he gets to section E he quips “This means EVERYONE (pauses, waits for all passengers to start moving in direction of the gate)… EXCEPT for section F!”

The residents of section F appear nonplussed, as the E section ticket holders file past them. Upon walking further into the gate, I see the man behind the curtain and resist powerful urges to smash his face repeatedly into the podium until his nose has made the deadly journey far past his brain.

As we are seated and carry-ons are securely stowed in the overhead compartments with all electrical devices powered down, the safety presentations begin on “Red,” our friendly personal touchscreen online entertainment monitor and travel guide. Personally, while flying in foreign countries my favorite part of the trip is when a beautiful flight attendant stands up and awkwardly goes through the motions with the seatbelt, oxygen mask, and life vest. Plus it’s a nice opportunity to stare before it gets creepy.

What I do not enjoy is a sarcastic, David Spade-esque video presentation depicting strange cartoons with bad things happening to them, and the cheap-laugh soliciting line about “if you’re one of the 99.9999% people who has never used a seatbelt before blah blah blah blah.” I suppose that it’s better than the ill-fated stand-up routine I once witnessed, delivered by the pilot of a Jet Blue flight from Jersey to Maine, where he actually used the line “But seriously folks, it may be a turbulent flight so feel free NOT to disturb the pretty lady seated next to you.” Please just fly the plane, bring the pillows and drinks, and shut the fuck up. Thank you.

Once safely in the air, I frantically attempt to access the drink service option on Red, as the only sustenance I have had all day thus far was a plate of anemic eggs and homefries at the Jerry Remy’s in airport terminal. I had been disappointed to discover that they did not start serving alcoholic beverages until 8AM, so once aboard I was determined to make up for lost time by keying in three cans of Heineken, as well as two bottles of water, for delivery to my coordinates. After 40 minutes, I begin to wonder if this fucking thing is broken, as I have yet to receive a goddamn drink, but not long after I see signs of life from the slow-moving flight attendants. Luckily, the soothing lavender and blue lights within the cabin are enough to pacify me until I receive my beers and begin furiously drinking them in an effort to steady my wings.

Because I do not want to deal with the trouble of contorting my gut in an effort to plug my phone charger into the outlet near my feet, I decide to browse the music selection on Red. I am able to locate a few artists that I enjoy, though the selection of actual songs is infuriatingly limited, to the point where if Red were a jukebox in a bar, someone would probably pull it off the wall and toss it through a window on an almost nightly basis. Inadequate as the selection is, it is far preferable to the blood curdling screams of the small Aryan child situated directly behind me, and as I get on to beer number 6, Coldplay’s Trouble is actually sounding pretty good!

That’s when things take a turn for the worse.

After giving Red the bad touch and ordering 2 more Heinekens, I am informed that I have effectively 86’d it from the plane. I think it’s important to clarify that I do not actually enjoy Heineken, but rather I simply find its flavor easy to ignore and superior to the alternatives. I am now left with the option of switching to straight liquor, a horrifying fabrication known as the “funkin’ margarita mixer,” or Bud Light. Because the flight is nearing its end, I choose Bud Light, and am instantly reminded what an utterly pointless creation this beer is. It is literally more watery than a glass of water, and I would probably have more luck getting drunk off of my hangover urine, but I press on, shotgun two of them, and next thing you know the tray tables are going up and it’s time to get this dog and pony show underway.

The Arrival

I appreciate my garish orange Nautica luggage because it is always very easy to spot at the baggage claim, not to mention I doubt anyone would ever try to steal it. To further discourage would-be thieves, I always weigh it down with at least three pairs of shoes, with shoetrees, whenever I travel for more than one day. Upon retrieving it I link up with the rest of my crew, including my co-worker Gary from Boston, at the closest airport bar. After choking down a double shot of Jameson, I fire up a large Peroni and ready myself to make a favorable first impression with wine professionals from all of the East Coast. I am informed that the limo driver charged with transporting us to the hotel has gotten a bit confused regarding the time and would return “presently,” after collecting luggage from the earlier arrivals. Dan, a portfolio manager from Rhode Island with a similar build to my own, except that he’s a ginger, leans over to me and says “Wait until you see this fucking guy – he’s about a million years old and I thought he was gonna throw his back out when he tried to lift my carry-on.”

Father Time, as he would be known from then on, proceeds to rumble up to the curb in a very old stretch SUV, which I would presume to be from circa 1988. Heeding Dan’s advice, I offer to put my own luggage into the back, for fear of having to wait for an ambulance to arrive and take this guy away in a stretcher. Twinkling blue and purple lights illuminate the interior of the limo, and as I pile myself into the corner window seat I am careful not to skid on the hardwood floors.

As the limo lurches into motion, we are acquainted with yet another new member of the group, who hails from Birmingham, Alabama. He prattles on about where he’s from, before referencing one of the restaurants on our itinerary for that evening. “Pier 23? Yeah, I spoke to a chef friend of mine who advised that we eat lightly there, if you know what I mean.” He pauses, implying something negative about the place, but when I am unable to make a connection I ask “Why? Because we’re hooking up an eight ball afterwards or something?” To me, it’s always a good sign when the first cocaine reference occurs 45 minutes in and is well received by the entire group. First Impression? Check.

After freshening up with a bracingly cold shower at the hotel, I meet Gary and his wife Clarissa to seek out an afternoon snack at a San Francisco institution known as Swan Oyster Depot. After a 25 minute uphill jaunt, we manage to procure three spots at the 18-seat bar right away, a feat which astounds anyone that I have described my visit to, as the line to get in is, allegedly, “always halfway down the block.” Swan has been around since 1912, and I would venture to say that the overall aesthetic of the place hasn’t changed much over the years. Large piles of fresh seafood on ice are laid out in plain view at both ends of the bar, with market prices for each displayed on the wall. The bar itself is lined with traditional accompaniments like Tabasco, lemon wedges, oyster crackers, and mignonette, all in endless quantities.


Because I have been jamming down cheap beer all morning, a bottle of cold, cheap Chateau La Tarciere Muscadet tastes like fucking heaven in contrast. The bartender pours all the way to the top of the glass, a practice that, while sometimes inappropriate, is perfectly reasonable here. We start with a dozen Kumamoto oysters, as well as two jumbo prawn cocktails, served with a generous carafe of mayo-driven Louis sauce, and a bowl of “Boston-style” chowder because why the fuck not? The oysters are cold and briny, marked by the cucumber characteristic that is most common with this particular species. I like mine simple, a squeeze of lemon and a quick hit of Tabasco.

We kill the first bottle of Muscadet in about 12 minutes, and while ordering another we ask the bartender to send out any dish of his choosing. Our confidence in him is rewarded with a plate of insanely fresh Halibut sashimi, complimented by rich, peppery olive oil and salty capers, which we quickly devour before requesting another order. Even though my barstool is wildly uncomfortable, I could have sat there and ate for several more hours, but alas we have impending dinner plans with our host, not to mention the line out the door has become quite sizeable during our stay.

While hoofing it, mostly downhill this time, back to our hotel, we stop to pick up a few bottles of wine to drink in our rooms in the interim before dinner. After trouncing down several glasses of Pieropan Soave, with a spot of pungent cheese, we are primed to meet the rest of the group, which is now about ten strong, at Pier 23. Initially, Dan has “a bone to pick” with me, claiming that I promised to go out and “get weird” with him this afternoon (which I do not remember doing), but after discovering that I share his affinity for heaping shots of Fernet Branca he seems to forget… until tomorrow. He also cannot help but point out that “He knew I would be fun to party with because I had missed two belt loops entirely,” which I confirm upon looking down. We are off to a great start, as I am, apparently, already a mess.

I would like to take a moment to discuss the phenomenon of Fernet Branca. I remember the first time I partook was with a Portland bartender named John Meyers. We finished the entire bottle, and I remember finding its bitter, medicinal quality weirdly enjoyable. At the time, it had yet to become available for purchase in Maine, so it remained a special treat that I enjoyed whenever I was on the road. Then, all of the sudden, it seemed like it was popping up everywhere, most prominently as a method for a bartender to subtlety identify himself as such to other bartenders simply by ordering it. San Francisco, as it turns out, consumes more than anywhere else in the country, with Boston running a close second. This brings me to the point of my story, which is that I am a firm believer in “when in Rome.”

When I received my itinerary for the trip about a week ago, I immediately set to researching each of the restaurants that we are scheduled to visit. Normally I am quite confident with my decisions, but in the case of Pier 23 I’ve got a bit of a dilemma. On the website, it claims that their specialty is whole roasted Dungeness Crab, though denoting it as “seasonal.” Earlier, when attempting to order crab at Swan Oyster, the bartender informed us that it is, in fact, out of season, and that they refuse to serve the frozen kind. This throws my initial plan into a tailspin, though I notice that Pier 23 is still offering it. Second, I had initially taken interest in the rib appetizer, but with crab now out of the picture I felt compelled to order seafood, as the restaurant is literally right on the water. Lastly, I am starting to get drunk and not all that hungry, and end up putting my focus on Fernet with Dan rather than on the menu where it belonged.

I manage to open the world’s biggest can of worms when Dan sees me snap a quick picture of the table setting.

“What are you, some kind of fucking blogger?” he asks, to which I reply that “Well, I hate that word but I do technically have a blog.” Immediately I realize that this was NOT the correct response, as every single activity for the next 3 days involves Dan asking if I’m “going to blog about it for the 7 people, including my mother, who actually read it.” Luckily I am able to dig into my arsenal and realize that he, and most gingers for that matter, particularly dislikes being referred to as “ginger balls,” which keeps him at bay long enough for me to get in at least a few pictures of my food here and there.

We power down two shots of Fernet apiece while we look the menu over. Amos, Dan’s travelling companion, gives us a look that implies “It may have been better for the world if you two hadn’t met.” Because I am starting to feel kind of fucked up and not super hungry, I have trouble focusing. Louis, the guy seated across from me, declares that the “Chorizo firecracker chimichanga sounds fucking awesome.” I glance at the Dungeness Crab on the menu, and then the ribs, but when the waitress actually comes around all hell breaks loose as I order like a total piker.

My carelessness is rewarded with a completely lackluster meal, starting with crab bisque (NO idea what the hell I was thinking here) that arrived lukewarm and badly in need of seasoning. This is followed by equally bland fish tacos, which lack breading, any element of crunch, any kind of crema, and anything remotely resembling flavor. I eat one out of three and pass them to Dan, who happily slaughters the remainder. To make matters worse, Gary, a few seats down, has ordered both the ribs AND the whole crab and each turn out to be fucking delicious. The ear-to-ear smile on his face as he devoured the crab will be burned into my memory forever. Even the goddamn chorizo firecracker chimichangas turn out to be better than the bullshit I had ordered! I promptly slug two more shots and three more glasses of wine before going outside for fresh air.

The weather in San Francisco makes me feel absolutely invincible, as it is cool and completely lacking in the stifling humidity that I am routinely subjected to in Boston. I chat up the doorman, informing him that I have come to the conclusion that this city has “Ideal conditions for the morbidly obese.” He, being a bit chubby himself, agrees wholeheartedly.

Back inside, I return to the table to find that someone at my end has begun the inevitable discussion of finding drugs. Louis is particularly fired up, not to mention he seems to think that I “Know a guy who knows a guy, if you know what I’m talking about.” I inform him that I have no such connections here, and promptly direct him towards Dan just to get him off my back.

To be honest, I haven’t done cocaine in over two years, and this is for a few reasons, the first of which being that the older I get, the more soul-crushing and awful the hangover from that stuff is. There is always the day after, when my body is completely fucked, followed by day two’s immeasurable depression, which generally prompts binge drinking just for the sake of feeling something else. Also, I have gained a lot of weight over the last few years, which makes me enjoy the drug significantly less as I spend more time wondering if my heart will explode than anything else. I know it sounds crazy, but one of my motivations to lose weight is so I can partake occasionally because, at the end of the day, it’s pretty fucking enjoyable. Needless to say, on a trip like this, I cannot afford to be derailed for 2 days this early on.

I have actually made plans to meet up with a random friend from Maine who works in a nearby restaurant. I accompany the group to a pool hall near our hotel, where I take down a few shots of tequila before promising Dan that I was only leaving for a short time to meet a friend and that I would definitely be back. Louis, who at one point looked as though he may pass out, is now asking practically every single person at the bar where he can find some blow, so I figure that this may be my cue to get the fuck out of here before he causes a scene with the wrong person.

I meet my friend at an Irish bar about a 25-minute walk away. She seems fine, and after a few shots and beers we decide to hit up a seedy bar in Chinatown for a nightcap. Then, something strange happens. Within the space of 5 minutes, she has gone from perfectly fine to completely shattered, to the point where I’m worried that she won’t be able to stand up. I finish my tequila and pay the bill, trying to figure out a strategy to get her home when I literally have no idea where she lives.

Outside, I am able to hail a cab, and eventually get her to tell us where she lives. I make sure that the cab driver has money and have them drop me off by my hotel. My head is still spinning from the whole experience when I suddenly remember that there is an IN N OUT Burger situated directly behind my hotel. There is no better way to put a long day of drinking to bed than to thrash a Double Double with a side of fries, so that is exactly what I do.

I’m not sure my head had even hit the pillow before I passed into a deep, dreamless sleep.